# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2325
_database_code_depnum_ccdc_archive 'CCDC 1405275'
_audit_update_record             
;
2015-06-07 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_audit_creation_date             2015-02-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 O3'
_chemical_formula_sum            'C21 H24 O3'
_chemical_formula_weight         324.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H28O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.8945(2)
_cell_length_b                   21.1600(5)
_cell_length_c                   9.0481(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.6300(19)
_cell_angle_gamma                90
_cell_volume                     1702.24(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5475
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      25.7420
_cell_measurement_theta_min      1.9100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.2247
_exptl_crystal_size_min          0.1276
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11096
_diffrn_reflns_point_group_measured_fraction_full 0.810
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.925
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3136  178.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
  2 omega  -80.00   54.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3136  -57.0000  120.0000 134

#__ type_ start__ end____ width___ exp.time_
  3 omega  -55.00   78.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4073   57.0000 -150.0000 133

#__ type_ start__ end____ width___ exp.time_
  4 omega  -57.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4073   77.0000  -30.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0354138000
_diffrn_orient_matrix_UB_12      0.0126801000
_diffrn_orient_matrix_UB_13      -0.0646900000
_diffrn_orient_matrix_UB_21      0.0148343000
_diffrn_orient_matrix_UB_22      -0.0284094000
_diffrn_orient_matrix_UB_23      -0.0384821000
_diffrn_orient_matrix_UB_31      -0.0699508000
_diffrn_orient_matrix_UB_32      -0.0124499000
_diffrn_orient_matrix_UB_33      0.0220484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.662
_reflns_Friedel_fraction_max     0.612
_reflns_number_gt                4559
_reflns_number_total             5072
_reflns_odcompleteness_completeness 86.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    ?
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5072
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.074
_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)+(0.0370P)²+0.1153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0847
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C12(H12), C13(H13), C19(H19), C20(H20), C23(H23), C29(H29),
 C30(H30), C34(H34), C37(H37), C39(H39)
2.b Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C41(H41A,H41B), C45(H45A,H45B), C48(H48A,H48B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C17(H17), C18(H18), C22(H22), C24(H24), C25(H25), C27(H27),
 C28(H28), C32(H32), C35(H35), C36(H36), C40(H40), C43(H43), C44(H44), C47(H47)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C42(H42A,H42B,H42C), C46(H46A,H46B,
 H46C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.9089(2) -0.01610(12) 1.0430(2) 0.0331(6) Uani 1 1 d . . . . .
O2 O -0.4369(2) 0.19287(12) 1.0790(3) 0.0372(6) Uani 1 1 d . . . . .
O3 O -1.2952(2) 0.32007(12) 1.4032(3) 0.0395(6) Uani 1 1 d . . . . .
O4 O -1.0553(2) 0.30628(12) 1.4927(2) 0.0355(6) Uani 1 1 d . . . . .
C5 C -1.0054(3) 0.24201(15) 0.9171(3) 0.0231(7) Uani 1 1 d . . . . .
H5 H -0.9385 0.2409 0.8329 0.028 Uiso 1 1 calc R . . . .
C6 C -0.7164(3) 0.04609(15) 1.4624(3) 0.0190(7) Uani 1 1 d . . . . .
H6 H -0.7052 0.0009 1.4836 0.023 Uiso 1 1 calc R . . . .
O7 O -0.2539(2) 0.12339(11) 1.3925(3) 0.0323(6) Uani 1 1 d . . . . .
C8 C -0.7063(3) 0.26473(15) 1.3055(3) 0.0259(8) Uani 1 1 d . . . . .
H8 H -0.6392 0.2723 1.3842 0.031 Uiso 1 1 calc R . . . .
C9 C -0.8635(3) 0.27660(15) 1.3257(3) 0.0236(7) Uani 1 1 d . . . . .
C10 C -0.4779(3) 0.06865(15) 1.3154(3) 0.0214(7) Uani 1 1 d . . . . .
C11 C -0.4142(3) -0.01937(15) 1.5688(4) 0.0241(7) Uani 1 1 d . . . . .
H11 H -0.4436 -0.0416 1.4841 0.029 Uiso 1 1 calc R . . . .
C12 C -0.5539(3) 0.07480(15) 1.4623(3) 0.0215(7) Uani 1 1 d . . . . .
H12 H -0.5616 0.1199 1.4855 0.026 Uiso 1 1 calc R . . . .
C13 C -0.9497(3) 0.01591(15) 1.3021(3) 0.0211(7) Uani 1 1 d . . . . .
H13 H -1.0220 0.0388 1.3617 0.025 Uiso 1 1 calc R . . . .
O14 O -1.1313(2) -0.03451(11) 1.1540(2) 0.0303(6) Uani 1 1 d . . . . .
C15 C -0.6602(3) 0.27445(15) 0.9155(3) 0.0197(7) Uani 1 1 d . . . . .
C16 C -0.4563(3) 0.04364(15) 1.5835(3) 0.0203(7) Uani 1 1 d . . . . .
C17 C -0.5464(3) 0.04517(16) 1.1934(3) 0.0237(7) Uani 1 1 d . . . . .
H17 H -0.4896 0.0386 1.1101 0.028 Uiso 1 1 calc R . . . .
C18 C -0.3287(3) -0.04953(17) 1.6792(3) 0.0294(8) Uani 1 1 d . . . . .
H18 H -0.3020 -0.0917 1.6680 0.035 Uiso 1 1 calc R . . . .
C19 C -0.7459(3) 0.24041(15) 1.0363(3) 0.0186(7) Uani 1 1 d . . . . .
H19 H -0.7552 0.1959 1.0076 0.022 Uiso 1 1 calc R . . . .
C20 C -0.8015(3) 0.07560(15) 1.5941(3) 0.0219(7) Uani 1 1 d . . . . .
H20 H -0.7241 0.0830 1.6714 0.026 Uiso 1 1 calc R . . . .
C21 C -0.7035(3) 0.02970(15) 1.1857(3) 0.0226(7) Uani 1 1 d . . . . .
C22 C -0.6252(3) 0.33815(15) 0.9303(3) 0.0227(7) Uani 1 1 d . . . . .
H22 H -0.6586 0.3606 1.0113 0.027 Uiso 1 1 calc R . . . .
C23 C -0.9080(3) 0.26762(15) 1.0493(3) 0.0192(7) Uani 1 1 d . . . . .
H23 H -0.9010 0.3136 1.0373 0.023 Uiso 1 1 calc R . . . .
C24 C -0.6081(3) 0.24192(16) 0.7933(3) 0.0244(7) Uani 1 1 d . . . . .
H24 H -0.6312 0.1993 0.7814 0.029 Uiso 1 1 calc R . . . .
C25 C -0.7630(4) 0.00014(16) 1.0665(3) 0.0277(8) Uani 1 1 d . . . . .
H25 H -0.6971 -0.0103 0.9924 0.033 Uiso 1 1 calc R . . . .
C26 C -0.6524(3) 0.24317(15) 1.1782(3) 0.0216(7) Uani 1 1 d . . . . .
C27 C -0.4986(4) 0.21967(16) 1.1792(4) 0.0308(8) Uani 1 1 d . . . . .
H27 H -0.4416 0.2258 1.2657 0.037 Uiso 1 1 calc R . . . .
C28 C -0.2833(4) -0.01711(17) 1.8053(4) 0.0311(9) Uani 1 1 d . . . . .
H28 H -0.2259 -0.0371 1.8790 0.037 Uiso 1 1 calc R . . . .
C29 C -0.7999(3) 0.05155(15) 1.3107(3) 0.0188(7) Uani 1 1 d . . . . .
H29 H -0.8221 0.0964 1.2941 0.023 Uiso 1 1 calc R . . . .
C30 C -0.9715(3) 0.25500(15) 1.2038(3) 0.0202(7) Uani 1 1 d . . . . .
H30 H -0.9827 0.2091 1.2139 0.024 Uiso 1 1 calc R . . . .
C31 C -1.0566(3) 0.17403(17) 0.9390(4) 0.0314(9) Uani 1 1 d . . . . .
H31A H -0.9726 0.1488 0.9723 0.047 Uiso 1 1 calc GR . . . .
H31B H -1.0962 0.1576 0.8470 0.047 Uiso 1 1 calc GR . . . .
H31C H -1.1333 0.1729 1.0115 0.047 Uiso 1 1 calc GR . . . .
C32 C -0.3242(3) 0.04528(18) 1.8201(3) 0.0299(8) Uani 1 1 d . . . . .
H32 H -0.2944 0.0674 1.9048 0.036 Uiso 1 1 calc R . . . .
C33 C -0.8665(3) 0.14093(15) 1.5574(3) 0.0252(8) Uani 1 1 d . . . . .
H33A H -0.7902 0.1667 1.5148 0.038 Uiso 1 1 calc GR . . . .
H33B H -0.9003 0.1605 1.6462 0.038 Uiso 1 1 calc GR . . . .
H33C H -0.9496 0.1365 1.4882 0.038 Uiso 1 1 calc GR . . . .
C34 C -1.1256(3) 0.28450(15) 1.2308(3) 0.0229(7) Uani 1 1 d . . . . .
H34 H -1.2009 0.2616 1.1705 0.027 Uiso 1 1 calc R . . . .
C35 C -0.4093(3) 0.07568(16) 1.7107(3) 0.0249(7) Uani 1 1 d . . . . .
H35 H -0.4352 0.1179 1.7226 0.030 Uiso 1 1 calc R . . . .
C36 C -0.3247(4) 0.09308(16) 1.3010(4) 0.0276(8) Uani 1 1 d . . . . .
H36 H -0.2773 0.0844 1.2129 0.033 Uiso 1 1 calc R . . . .
C37 C -1.0158(3) 0.00951(17) 1.1466(3) 0.0273(8) Uani 1 1 d . . . . .
H37 H -1.0550 0.0502 1.1113 0.033 Uiso 1 1 calc R . . . .
C38 C -1.0991(4) -0.07645(16) 1.2786(3) 0.0277(8) Uani 1 1 d . . . . .
H38A H -1.0899 -0.1198 1.2451 0.033 Uiso 1 1 calc R . . . .
H38B H -1.1789 -0.0743 1.3493 0.033 Uiso 1 1 calc R . . . .
C39 C -1.1711(4) 0.28077(17) 1.3911(3) 0.0297(8) Uani 1 1 d . . . . .
H39 H -1.1964 0.2372 1.4178 0.036 Uiso 1 1 calc R . . . .
C40 C -0.9117(4) 0.29836(16) 1.4549(3) 0.0301(8) Uani 1 1 d . . . . .
H40 H -0.8382 0.3091 1.5256 0.036 Uiso 1 1 calc R . . . .
C41 C -0.9514(3) -0.05364(15) 1.3486(3) 0.0235(7) Uani 1 1 d . . . . .
H41A H -0.8665 -0.0764 1.3100 0.028 Uiso 1 1 calc R . . . .
H41B H -0.9508 -0.0580 1.4554 0.028 Uiso 1 1 calc R . . . .
C42 C -0.9191(4) 0.03486(16) 1.6662(4) 0.0318(8) Uani 1 1 d . . . . .
H42A H -1.0034 0.0292 1.5989 0.048 Uiso 1 1 calc GR . . . .
H42B H -0.9519 0.0551 1.7545 0.048 Uiso 1 1 calc GR . . . .
H42C H -0.8764 -0.0056 1.6908 0.048 Uiso 1 1 calc GR . . . .
C43 C -0.5224(3) 0.27211(18) 0.6894(3) 0.0290(8) Uani 1 1 d . . . . .
H43 H -0.4875 0.2497 0.6090 0.035 Uiso 1 1 calc R . . . .
C44 C -0.5403(3) 0.36861(17) 0.8244(4) 0.0293(8) Uani 1 1 d . . . . .
H44 H -0.5185 0.4114 0.8346 0.035 Uiso 1 1 calc R . . . .
C45 C -1.2913(4) 0.36755(18) 1.2870(4) 0.0401(10) Uani 1 1 d . . . . .
H45A H -1.2897 0.4097 1.3292 0.048 Uiso 1 1 calc R . . . .
H45B H -1.3789 0.3637 1.2212 0.048 Uiso 1 1 calc R . . . .
C46 C -1.1392(3) 0.28296(18) 0.8671(4) 0.0341(9) Uani 1 1 d . . . . .
H46A H -1.2189 0.2783 0.9355 0.051 Uiso 1 1 calc GR . . . .
H46B H -1.1740 0.2699 0.7704 0.051 Uiso 1 1 calc GR . . . .
H46C H -1.1087 0.3264 0.8639 0.051 Uiso 1 1 calc GR . . . .
C47 C -0.4885(3) 0.33562(18) 0.7049(3) 0.0304(8) Uani 1 1 d . . . . .
H47 H -0.4311 0.3559 0.6349 0.036 Uiso 1 1 calc R . . . .
C48 C -1.1476(4) 0.35517(15) 1.2031(4) 0.0300(8) Uani 1 1 d . . . . .
H48A H -1.0637 0.3796 1.2433 0.036 Uiso 1 1 calc R . . . .
H48B H -1.1611 0.3643 1.0985 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C25 1.353(4) . ?
O1 C37 1.459(4) . ?
O2 C27 1.214(4) . ?
O3 C39 1.389(4) . ?
O3 C45 1.456(4) . ?
O4 C39 1.464(4) . ?
O4 C40 1.342(4) . ?
C5 C23 1.554(4) . ?
C5 C31 1.523(5) . ?
C5 C46 1.530(4) . ?
C6 C12 1.567(4) . ?
C6 C20 1.560(4) . ?
C6 C29 1.547(4) . ?
O7 C36 1.210(4) . ?
C8 C9 1.437(4) . ?
C8 C26 1.340(4) . ?
C9 C30 1.513(4) . ?
C9 C40 1.338(4) . ?
C10 C12 1.514(4) . ?
C10 C17 1.341(4) . ?
C10 C36 1.467(4) . ?
C11 C16 1.392(4) . ?
C11 C18 1.393(4) . ?
C12 C16 1.529(4) . ?
C13 C29 1.531(4) . ?
C13 C37 1.515(4) . ?
C13 C41 1.531(4) . ?
O14 C37 1.390(4) . ?
O14 C38 1.457(4) . ?
C15 C19 1.530(4) . ?
C15 C22 1.389(4) . ?
C15 C24 1.393(4) . ?
C16 C35 1.390(4) . ?
C17 C21 1.434(4) . ?
C18 C28 1.381(4) . ?
C19 C23 1.560(4) . ?
C19 C26 1.511(4) . ?
C20 C33 1.531(4) . ?
C20 C42 1.517(4) . ?
C21 C25 1.342(4) . ?
C21 C29 1.511(4) . ?
C22 C44 1.394(4) . ?
C23 C30 1.547(4) . ?
C24 C43 1.383(4) . ?
C26 C27 1.455(4) . ?
C28 C32 1.377(5) . ?
C30 C34 1.532(4) . ?
C32 C35 1.387(4) . ?
C34 C39 1.518(4) . ?
C34 C48 1.528(4) . ?
C38 C41 1.521(4) . ?
C43 C47 1.384(5) . ?
C44 C47 1.377(5) . ?
C45 C48 1.528(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 O1 C37 116.4(2) . . ?
C39 O3 C45 108.7(2) . . ?
C40 O4 C39 116.8(2) . . ?
C31 C5 C23 113.0(3) . . ?
C31 C5 C46 109.9(3) . . ?
C46 C5 C23 116.2(3) . . ?
C20 C6 C12 108.2(2) . . ?
C29 C6 C12 112.9(2) . . ?
C29 C6 C20 114.6(2) . . ?
C26 C8 C9 122.8(3) . . ?
C8 C9 C30 117.0(3) . . ?
C40 C9 C8 120.5(3) . . ?
C40 C9 C30 121.9(3) . . ?
C17 C10 C12 123.4(3) . . ?
C17 C10 C36 117.3(3) . . ?
C36 C10 C12 119.1(3) . . ?
C16 C11 C18 120.8(3) . . ?
C10 C12 C6 113.7(2) . . ?
C10 C12 C16 109.5(2) . . ?
C16 C12 C6 109.7(2) . . ?
C29 C13 C41 118.4(2) . . ?
C37 C13 C29 113.9(2) . . ?
C37 C13 C41 99.4(2) . . ?
C37 O14 C38 108.4(2) . . ?
C22 C15 C19 120.2(3) . . ?
C22 C15 C24 118.5(3) . . ?
C24 C15 C19 121.2(3) . . ?
C11 C16 C12 119.5(3) . . ?
C35 C16 C11 118.1(3) . . ?
C35 C16 C12 122.3(3) . . ?
C10 C17 C21 122.9(3) . . ?
C28 C18 C11 120.4(3) . . ?
C15 C19 C23 111.1(2) . . ?
C26 C19 C15 108.4(2) . . ?
C26 C19 C23 114.2(2) . . ?
C33 C20 C6 112.6(2) . . ?
C42 C20 C6 117.2(3) . . ?
C42 C20 C33 110.2(2) . . ?
C17 C21 C29 117.8(3) . . ?
C25 C21 C17 120.5(3) . . ?
C25 C21 C29 121.6(3) . . ?
C15 C22 C44 120.5(3) . . ?
C5 C23 C19 108.0(2) . . ?
C30 C23 C5 115.2(2) . . ?
C30 C23 C19 111.5(2) . . ?
C43 C24 C15 120.9(3) . . ?
C21 C25 O1 126.9(3) . . ?
C8 C26 C19 122.8(3) . . ?
C8 C26 C27 118.1(3) . . ?
C27 C26 C19 119.1(3) . . ?
O2 C27 C26 126.9(3) . . ?
C32 C28 C18 119.0(3) . . ?
C13 C29 C6 113.8(2) . . ?
C21 C29 C6 111.9(2) . . ?
C21 C29 C13 108.8(2) . . ?
C9 C30 C23 111.5(2) . . ?
C9 C30 C34 108.2(2) . . ?
C34 C30 C23 115.2(2) . . ?
C28 C32 C35 121.1(3) . . ?
C39 C34 C30 113.3(3) . . ?
C39 C34 C48 99.9(3) . . ?
C48 C34 C30 118.9(3) . . ?
C32 C35 C16 120.6(3) . . ?
O7 C36 C10 126.3(3) . . ?
O1 C37 C13 112.8(2) . . ?
O14 C37 O1 106.2(3) . . ?
O14 C37 C13 106.5(2) . . ?
O14 C38 C41 106.1(2) . . ?
O3 C39 O4 106.0(3) . . ?
O3 C39 C34 106.1(3) . . ?
O4 C39 C34 112.3(2) . . ?
C9 C40 O4 126.6(3) . . ?
C38 C41 C13 101.9(2) . . ?
C24 C43 C47 120.2(3) . . ?
C47 C44 C22 120.3(3) . . ?
O3 C45 C48 106.1(3) . . ?
C44 C47 C43 119.6(3) . . ?
C45 C48 C34 101.0(3) . . ?

_shelx_SHELXL_version_number     2014/7
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
-12 -5 -3 0.0200 -11.9972 -4.9964 -2.9996 0.5556 0.0794 0.8353
-2 14 -11 0.0763 -2.0055 14.0038 -10.9881 0.9594 -0.0047 -0.2763
0 -9 12 0.1084 0.0054 -9.0028 11.9875 -0.8898 -0.2055 0.3760
0 -25 7 0.1504 0.0066 -25.0039 6.9900 -0.7695 0.4415 0.4650
13 -1 0 0.0801 12.9971 -1.0042 0.0017 -0.4731 0.2213 -0.8966
12 2 -5 0.1011 11.9952 1.9972 -4.9933 -0.0765 0.3134 -0.9740
-12 -4 5 0.0898 -11.9949 -3.9975 4.9930 0.0511 -0.2565 0.9989
-1 29 3 0.1093 -1.0039 29.0032 3.0011 0.2092 -0.9543 -0.2247
12 4 4 0.1052 11.9977 3.9962 3.9986 -0.6329 -0.0894 -0.8008
2 -28 -5 0.0927 1.9998 -27.9766 -4.9964 -0.1024 1.0167 0.0983

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_2409
_database_code_depnum_ccdc_archive 'CCDC 1405277'
_audit_update_record             
;
2015-06-07 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C18 H20 O3'
_chemical_formula_sum            'C18 H20 O3'
_chemical_formula_weight         284.36
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         C17H17O3
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   7.503(3)
_cell_length_b                   10.304(5)
_cell_length_c                   10.253(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.82(4)
_cell_angle_gamma                90
_cell_volume                     791.7(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    417
_cell_measurement_temperature    293.02(10)
_cell_measurement_theta_max      18.0400
_cell_measurement_theta_min      2.7900
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.986
_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_density_diffrn    1.1928
_exptl_crystal_F_000             304.1600
_exptl_crystal_size_max          0.1711
_exptl_crystal_size_mid          0.1298
_exptl_crystal_size_min          0.0641
_diffrn_reflns_av_R_equivalents  0.1847
_diffrn_reflns_av_unetI/netI     0.3138
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5304
_diffrn_reflns_theta_full        29.1780
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         2.72
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.6796
_diffrn_measured_fraction_theta_max 0.6796
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   82.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       10.1632   38.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00   33.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       10.1632  -57.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega   43.00   74.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       10.1632 -178.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega  -13.00   20.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.4132  -99.0000 -120.0000 33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0237607000
_diffrn_orient_matrix_UB_12      -0.0662916000
_diffrn_orient_matrix_UB_13      -0.0082078000
_diffrn_orient_matrix_UB_21      0.0456488000
_diffrn_orient_matrix_UB_22      -0.0019161000
_diffrn_orient_matrix_UB_23      -0.0589231000
_diffrn_orient_matrix_UB_31      0.0793295000
_diffrn_orient_matrix_UB_32      -0.0186532000
_diffrn_orient_matrix_UB_33      0.0355990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.474
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              13
_reflns_limit_l_min              -12
_reflns_number_gt                988
_reflns_number_total             2910
_reflns_odcompleteness_completeness 99.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(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  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.8573
_refine_diff_density_min         -0.7719
_refine_diff_density_rms         0.1931
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -3.6(11)
_refine_ls_d_res_high            0.7289
_refine_ls_d_res_low             7.4940
_refine_ls_goodness_of_fit_ref   0.9590
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2768
_refine_ls_R_factor_gt           0.1040
_refine_ls_restrained_S_all      0.9590
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1049P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2241
_refine_ls_wR_factor_ref         0.3441
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3AA(H3AA), C4AA(H4AA), C7AA(H7AA), C9AA(H9AA), C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C6AA(H6AA), C8AA(H8AA), C2BA(H2BA), C3BA(H3BA), C4BA(H4BA), C6BA(H6BA),
 C7BA(H7BA), C9BA(H9BA)
2.c Idealised Me refined as rotating group:
 C0BA(H0BA,H0BB,H0BC), C5BA(H5BA,H5BB,H5BC)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
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_refinement_flags_posn
O O -0.3754(9) -0.5786(7) -0.3852(7) 0.052(2) Uani 1.000000 .
O2 O -0.3878(9) -0.8049(8) -1.0601(7) 0.0536(19) Uani 1.000000 .
C2AA C -0.4141(13) -0.6502(9) -0.6107(10) 0.041(3) Uani 1.000000 .
C3AA C -0.7158(12) -0.7208(11) -0.7117(9) 0.044(3) Uani 1.000000 .
H3AA H -0.7467(12) -0.6299(11) -0.7300(9) 0.053(3) Uiso 1.000000 R
C4AA C -0.5914(11) -0.7241(10) -0.5858(9) 0.040(2) Uani 1.000000 .
H4AA H -0.5596(11) -0.8151(10) -0.5698(9) 0.048(3) Uiso 1.000000 R
C5AA C -0.4372(13) -0.7137(10) -0.8457(10) 0.044(3) Uani 1.000000 .
C6AA C -0.3271(13) -0.5864(11) -0.5103(11) 0.052(3) Uani 1.000000 .
H6AA H -0.2228(13) -0.5433(11) -0.5300(11) 0.062(4) Uiso 1.000000 R
C7AA C -0.6279(11) -0.7783(10) -0.8366(9) 0.043(3) Uani 1.000000 .
H7AA H -0.6143(11) -0.8724(10) -0.8267(9) 0.051(3) Uiso 1.000000 R
C8AA C -0.3527(13) -0.6551(10) -0.7425(11) 0.045(3) Uani 1.000000 .
H8AA H -0.2452(13) -0.6140(10) -0.7572(11) 0.054(3) Uiso 1.000000 R
C9AA C -0.6682(13) -0.6717(10) -0.4593(10) 0.043(3) Uani 1.000000 .
H9AA H -0.7625(13) -0.7310(10) -0.4338(10) 0.052(3) Uiso 1.000000 R
C0BA C -0.8943(12) -0.7963(11) -0.6879(9) 0.048(3) Uani 1.000000 .
H0Ba H -0.8675(15) -0.8854(17) -0.668(6) 0.073(4) Uiso 1.000000 GR
H0Bb H -0.952(4) -0.758(4) -0.616(4) 0.073(4) Uiso 1.000000 GR
H0Bc H -0.972(4) -0.792(6) -0.765(2) 0.073(4) Uiso 1.000000 GR
C2BA C -0.8835(15) -0.5937(12) -1.1145(11) 0.057(3) Uani 1.000000 .
H2BA H -0.9001(15) -0.5083(12) -1.1420(11) 0.068(4) Uiso 1.000000 R
C3BA C -0.7688(15) -0.6190(11) -1.0037(10) 0.049(3) Uani 1.000000 .
C4BA C -0.9712(15) -0.6914(14) -1.1826(13) 0.068(4) Uani 1.000000 .
H4BA H -1.0469(15) -0.6712(14) -1.2543(13) 0.081(5) Uiso 1.000000 R
C5BA C -0.7521(14) -0.5323(11) -0.4782(10) 0.052(3) Uani 1.000000 .
H5Ba H -0.671(4) -0.478(2) -0.523(6) 0.077(5) Uiso 1.000000 GR
H5Bb H -0.863(5) -0.5388(13) -0.528(6) 0.077(5) Uiso 1.000000 GR
H5Bc H -0.773(9) -0.495(3) -0.3943(11) 0.077(5) Uiso 1.000000 GR
C6BA C -0.8295(14) -0.8479(11) -1.0321(11) 0.054(3) Uani 1.000000 .
H6BA H -0.8092(14) -0.9336(11) -1.0067(11) 0.065(4) Uiso 1.000000 R
C7BA C -0.3414(14) -0.7353(12) -0.9644(11) 0.055(3) Uani 1.000000 .
C8BA C -0.7436(12) -0.7492(11) -0.9589(10) 0.048(3) Uani 1.000000 .
C9BA C -0.9469(15) -0.8237(12) -1.1441(11) 0.063(3) Uani 1.000000 .
H9BA H -1.0046(15) -0.8910(12) -1.1895(11) 0.075(4) Uiso 1.000000 R
C1 C -0.5231(14) -0.6686(10) -0.3484(12) 0.050(3) Uani 1.000000 .
O1 O -0.4508(10) -0.7966(7) -0.3313(7) 0.056(2) Uani 1.000000 .
H3BA H -0.7099(15) -0.5510(11) -0.9602(10) 0.059(4) Uiso 1.000000 R
H7BA H -0.2331(14) -0.6921(12) -0.9694(11) 0.066(4) Uiso 1.000000 R
H1 H -0.5740(14) -0.6391(10) -0.2673(12) 0.060(3) Uiso 1.000000 R
H1a H -0.415(15) -0.806(4) -0.255(3) 0.084(3) Uiso 1.000000 GR


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
O C6AA 1.353(13) . ?
O C1 1.507(13) . ?
O2 C7BA 1.251(12) . ?
C2AA C4AA 1.564(13) . ?
C2AA C6AA 1.361(14) . ?
C2AA C8AA 1.449(14) . ?
C3AA C4AA 1.556(12) . ?
C3AA C7AA 1.584(13) . ?
C3AA C0BA 1.578(13) . ?
C4AA C9AA 1.542(13) . ?
C5AA C7AA 1.585(13) . ?
C5AA C8AA 1.349(13) . ?
C5AA C7BA 1.461(14) . ?
C7AA C8BA 1.520(13) . ?
C9AA C5BA 1.577(14) . ?
C9AA C1 1.535(13) . ?
C2BA C3BA 1.415(14) . ?
C2BA C4BA 1.375(16) . ?
C3BA C8BA 1.428(15) . ?
C4BA C9BA 1.429(17) . ?
C6BA C8BA 1.402(14) . ?
C6BA C9BA 1.435(14) . ?
C1 O1 1.433(12) . ?

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
C1 O C6AA 115.8(8) . . ?
C6AA C2AA C4AA 119.5(9) . . ?
C8AA C2AA C4AA 116.6(8) . . ?
C8AA C2AA C6AA 124.0(10) . . ?
C7AA C3AA C4AA 113.9(7) . . ?
C0BA C3AA C4AA 109.9(8) . . ?
C0BA C3AA C7AA 109.3(8) . . ?
C3AA C4AA C2AA 109.5(8) . . ?
C9AA C4AA C2AA 108.9(8) . . ?
C9AA C4AA C3AA 117.1(7) . . ?
C8AA C5AA C7AA 122.2(9) . . ?
C7BA C5AA C7AA 117.9(9) . . ?
C7BA C5AA C8AA 119.3(10) . . ?
C2AA C6AA O 127.3(10) . . ?
C5AA C7AA C3AA 107.7(8) . . ?
C8BA C7AA C3AA 110.4(7) . . ?
C8BA C7AA C5AA 110.5(8) . . ?
C5AA C8AA C2AA 126.0(10) . . ?
C5BA C9AA C4AA 112.3(9) . . ?
C1 C9AA C4AA 110.5(8) . . ?
C1 C9AA C5BA 109.6(8) . . ?
C4BA C2BA C3BA 122.0(12) . . ?
C8BA C3BA C2BA 119.8(10) . . ?
C9BA C4BA C2BA 120.5(11) . . ?
C9BA C6BA C8BA 123.4(11) . . ?
C5AA C7BA O2 127.7(11) . . ?
C3BA C8BA C7AA 120.8(10) . . ?
C6BA C8BA C7AA 121.8(10) . . ?
C6BA C8BA C3BA 117.4(9) . . ?
C6BA C9BA C4BA 116.9(11) . . ?
C9AA C1 O 109.3(8) . . ?
O1 C1 O 108.6(8) . . ?
O1 C1 C9AA 108.8(8) . . ?

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 -4 5 0.0512 0.0003 -3.9987 4.9978 0.2240 -0.2868 0.2525
0 4 -5 0.0618 -0.0003 3.9987 -4.9978 -0.2240 0.2868 -0.2525
5 1 1 0.0779 5.0001 1.0019 1.0003 -0.1934 0.1674 0.4136
-5 -1 0 0.0846 -5.0000 -1.0019 -0.0007 0.1852 -0.2263 -0.3780
-1 4 5 0.0378 -0.9995 3.9988 4.9975 -0.2824 -0.3478 0.0240
1 -4 -5 0.0263 0.9995 -3.9988 -4.9975 0.2824 0.3478 -0.0240

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2014_12_16
_database_code_depnum_ccdc_archive 'CCDC 1405309'
_audit_update_record             
;
2015-06-07 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_audit_creation_date             2015-02-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H28 O3'
_chemical_formula_sum            'C22 H28 O3'
_chemical_formula_weight         340.47
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'C22 H28 O3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   7.5376(6)
_cell_length_b                   10.5784(10)
_cell_length_c                   23.8774(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1903.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1134
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      19.1520
_cell_measurement_theta_min      2.5550
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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 yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1877
_exptl_crystal_description       block
_exptl_crystal_F_000             736.3612
_exptl_crystal_size_max          0.1956
_exptl_crystal_size_mid          0.1687
_exptl_crystal_size_min          0.0889
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.1618
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7273
_diffrn_reflns_theta_full        25.9611
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         1.71
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.8311
_diffrn_measured_fraction_theta_max 0.8311
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -34.00  103.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       12.2354   38.0000  -60.0000 137

#__ type_ start__ end____ width___ exp.time_
  2 omega  -89.00  -35.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       12.2354 -178.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00    5.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       12.2354  -99.0000  -90.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0455059000
_diffrn_orient_matrix_UB_12      0.0033576000
_diffrn_orient_matrix_UB_13      -0.0259313000
_diffrn_orient_matrix_UB_21      0.0563994000
_diffrn_orient_matrix_UB_22      -0.0476371000
_diffrn_orient_matrix_UB_23      -0.0110163000
_diffrn_orient_matrix_UB_31      -0.0600700000
_diffrn_orient_matrix_UB_32      -0.0471209000
_diffrn_orient_matrix_UB_33      0.0093362000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.764
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              29
_reflns_limit_l_min              -28
_reflns_number_gt                1813
_reflns_number_total             3091
_reflns_odcompleteness_completeness 85.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.17
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.5048
_refine_diff_density_min         -0.5567
_refine_diff_density_rms         0.1256
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.9(15)
_refine_ls_d_res_high            0.8118
_refine_ls_d_res_low             11.9387
_refine_ls_goodness_of_fit_ref   1.0032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    47
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.0032
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1300
_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:
 C12(H12), C4(H4), C6(H6), C3(H3), C19(H19), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C15(H15), C14(H14), C8(H8), C11(H11), C16(H16), C9(H9), C17(H17)
2.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C22(H22a,H22b,H22c), C1(H1a,H1b,H1c), C5(H5a,H5b,H5c)
;
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_refinement_flags_posn
O2 O -0.5538(4) -0.6821(3) -0.09630(11) 0.0223(8) Uani 1.000000 .
O1 O -0.8621(4) -0.6861(3) -0.11019(11) 0.0246(8) Uani 1.000000 .
C10 C -0.6539(6) -1.1184(5) -0.13226(17) 0.0180(11) Uani 1.000000 .
O3 O -0.6981(4) -1.3391(3) -0.14926(13) 0.0307(9) Uani 1.000000 .
C7 C -0.5714(5) -0.8998(4) -0.12492(17) 0.0167(11) Uani 1.000000 .
C12 C -0.8410(6) -1.0824(4) -0.15162(16) 0.0166(11) Uani 1.000000 .
H12 H -0.8715(6) -1.1360(4) -0.18368(16) 0.0199(13) Uiso 1.000000 R
C13 C -0.9638(6) -1.1177(4) -0.10323(17) 0.0171(11) Uani 1.000000 .
C18 C -1.0630(6) -1.2287(5) -0.10413(18) 0.0237(12) Uani 1.000000 .
H18 H -1.0610(6) -1.2795(5) -0.13591(18) 0.0284(14) Uiso 1.000000 R
C15 C -1.0736(6) -1.0804(5) -0.00892(18) 0.0280(13) Uani 1.000000 .
H15 H -1.0770(6) -1.0303(5) 0.02305(18) 0.0336(15) Uiso 1.000000 R
C4 C -0.6800(6) -0.7319(4) -0.18830(17) 0.0192(11) Uani 1.000000 .
H4 H -0.7817(6) -0.7119(4) -0.21228(17) 0.0230(14) Uiso 1.000000 R
C14 C -0.9688(6) -1.0439(4) -0.05449(17) 0.0219(12) Uani 1.000000 .
H14 H -0.9019(6) -0.9701(4) -0.05243(17) 0.0263(14) Uiso 1.000000 R
C8 C -0.5125(6) -0.8073(5) -0.09123(18) 0.0234(12) Uani 1.000000 .
H8 H -0.4374(6) -0.8304(5) -0.06206(18) 0.0281(15) Uiso 1.000000 R
C6 C -0.6814(6) -0.8754(4) -0.17620(17) 0.0210(12) Uani 1.000000 .
H6 H -0.6206(6) -0.9165(4) -0.20759(17) 0.0252(14) Uiso 1.000000 R
C3 C -0.6962(6) -0.6563(4) -0.13490(18) 0.0248(12) Uani 1.000000 .
H3 H -0.6947(6) -0.5661(4) -0.14428(18) 0.0298(15) Uiso 1.000000 R
C11 C -0.6088(6) -1.2532(5) -0.13077(18) 0.0259(13) Uani 1.000000 .
H11 H -0.5016(6) -1.2749(5) -0.11408(18) 0.0311(15) Uiso 1.000000 R
C19 C -0.8633(5) -0.9410(4) -0.17006(16) 0.0180(11) Uani 1.000000 .
H19 H -0.9261(5) -0.8978(4) -0.13967(16) 0.0216(14) Uiso 1.000000 R
C2 C -0.9175(6) -0.5995(5) -0.06745(18) 0.0275(13) Uani 1.000000 .
H2a H -0.8427(6) -0.6082(5) -0.03461(18) 0.0330(15) Uiso 1.000000 R
H2b H -0.9088(6) -0.5132(5) -0.08089(18) 0.0330(15) Uiso 1.000000 R
C21 C -0.9020(5) -0.9877(5) -0.27638(16) 0.0292(13) Uani 1.000000 .
H21a H -0.7911(18) -0.9473(17) -0.2848(6) 0.044(2) Uiso 1.000000 GR
H21b H -0.883(3) -1.0764(6) -0.2705(4) 0.044(2) Uiso 1.000000 GR
H21c H -0.9825(17) -0.976(2) -0.3071(3) 0.044(2) Uiso 1.000000 GR
C16 C -1.1713(6) -1.1893(5) -0.01100(19) 0.0290(13) Uani 1.000000 .
H16 H -1.2417(6) -1.2124(5) 0.01929(19) 0.0348(15) Uiso 1.000000 R
C20 C -0.9817(6) -0.9291(4) -0.22325(17) 0.0223(12) Uani 1.000000 .
H20 H -0.9941(6) -0.8384(4) -0.23071(17) 0.0267(14) Uiso 1.000000 R
C9 C -0.5382(6) -1.0323(4) -0.11425(17) 0.0217(12) Uani 1.000000 .
H9 H -0.4368(6) -1.0572(4) -0.09497(17) 0.0261(14) Uiso 1.000000 R
C22 C -1.1678(5) -0.9791(4) -0.21247(17) 0.0259(12) Uani 1.000000 .
H22a H -1.1632(7) -1.0689(5) -0.2071(10) 0.0389(19) Uiso 1.000000 GR
H22b H -1.2155(14) -0.9397(18) -0.1795(6) 0.0389(19) Uiso 1.000000 GR
H22c H -1.2422(10) -0.960(2) -0.2440(5) 0.0389(19) Uiso 1.000000 GR
C17 C -1.1650(6) -1.2650(5) -0.05823(19) 0.0287(13) Uani 1.000000 .
H17 H -1.2290(6) -1.3401(5) -0.05933(19) 0.0344(15) Uiso 1.000000 R
C1 C -1.1085(5) -0.6309(5) -0.05293(19) 0.0320(14) Uani 1.000000 .
H1a H -1.1817(8) -0.620(2) -0.0855(4) 0.048(2) Uiso 1.000000 GR
H1b H -1.1159(8) -0.7170(9) -0.0405(10) 0.048(2) Uiso 1.000000 GR
H1c H -1.1488(13) -0.5757(17) -0.0237(8) 0.048(2) Uiso 1.000000 GR
C5 C -0.5095(5) -0.6937(4) -0.21929(17) 0.0293(13) Uani 1.000000 .
H5a H -0.4082(5) -0.719(2) -0.1977(5) 0.0440(19) Uiso 1.000000 GR
H5b H -0.5062(17) -0.7345(19) -0.2552(5) 0.0440(19) Uiso 1.000000 GR
H5c H -0.5078(17) -0.6037(5) -0.2244(9) 0.0440(19) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C8 1.366(5) . ?
O2 C3 1.441(5) . ?
O1 C3 1.418(5) . ?
O1 C2 1.433(5) . ?
C10 C12 1.533(6) . ?
C10 C11 1.466(7) . ?
C10 C9 1.332(6) . ?
O3 C11 1.214(5) . ?
C7 C8 1.342(6) . ?
C7 C6 1.501(5) . ?
C7 C9 1.446(6) . ?
C12 C13 1.527(5) . ?
C12 C19 1.568(6) . ?
C13 C18 1.393(6) . ?
C13 C14 1.402(5) . ?
C18 C17 1.393(6) . ?
C15 C14 1.399(5) . ?
C15 C16 1.368(6) . ?
C4 C6 1.545(6) . ?
C4 C3 1.510(6) . ?
C4 C5 1.537(5) . ?
C6 C19 1.544(6) . ?
C19 C20 1.557(5) . ?
C2 C1 1.518(5) . ?
C21 C20 1.534(5) . ?
C16 C17 1.384(6) . ?
C20 C22 1.521(5) . ?

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
C3 O2 C8 114.2(3) . . ?
C2 O1 C3 114.3(3) . . ?
C11 C10 C12 117.5(4) . . ?
C9 C10 C12 122.0(4) . . ?
C9 C10 C11 120.3(4) . . ?
C6 C7 C8 123.1(4) . . ?
C9 C7 C8 122.9(4) . . ?
C9 C7 C6 114.0(4) . . ?
C13 C12 C10 105.6(3) . . ?
C19 C12 C10 114.9(4) . . ?
C19 C12 C13 112.4(3) . . ?
C18 C13 C12 121.3(4) . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 C18 117.9(4) . . ?
C17 C18 C13 121.1(4) . . ?
C16 C15 C14 120.6(4) . . ?
C3 C4 C6 111.2(4) . . ?
C5 C4 C6 110.8(4) . . ?
C5 C4 C3 109.6(4) . . ?
C15 C14 C13 120.4(4) . . ?
C7 C8 O2 125.3(4) . . ?
C4 C6 C7 108.5(4) . . ?
C19 C6 C7 109.6(3) . . ?
C19 C6 C4 117.8(4) . . ?
O1 C3 O2 110.4(3) . . ?
C4 C3 O2 112.3(4) . . ?
C4 C3 O1 107.8(4) . . ?
O3 C11 C10 126.2(4) . . ?
C6 C19 C12 111.1(3) . . ?
C20 C19 C12 111.6(4) . . ?
C20 C19 C6 113.3(3) . . ?
C1 C2 O1 107.4(4) . . ?
C17 C16 C15 119.9(5) . . ?
C21 C20 C19 114.7(3) . . ?
C22 C20 C19 111.2(3) . . ?
C22 C20 C21 111.1(4) . . ?
C7 C9 C10 119.5(4) . . ?
C16 C17 C18 120.1(5) . . ?

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
9 8 6 0.0683 8.9971 8.0108 6.0286 -0.5389 0.0594 -0.8616
-3 14 9 0.1001 -2.9991 13.9956 8.9625 -0.0489 -0.9346 -0.3957
5 -11 -13 0.1003 5.0016 -10.9972 -12.9593 0.0715 0.9487 0.0968
-8 -9 13 0.0315 -8.0072 -8.9970 12.9812 -0.0025 -0.1660 1.0261
8 8 -13 0.0704 8.0069 7.9975 -12.9795 -0.0009 0.2136 -0.9790
0 8 -29 0.0761 0.0171 7.9778 -29.0196 0.7785 -0.0594 -0.6479
3 -5 30 0.1006 2.9825 -4.9750 30.0284 -0.9311 0.0744 0.3356
-9 -6 -13 0.0093 -8.9929 -6.0161 -13.0335 0.7270 -0.0770 0.7020
4 -12 -15 0.0614 4.0000 -12.0000 -15.0000 0.1667 0.9625 0.1851
-2 -6 30 0.0672 -2.0000 -6.0000 30.0001 -0.7071 -0.1575 0.6830

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_lal106_0m
_database_code_depnum_ccdc_archive 'CCDC 1408759'
_audit_update_record             
;
2015-06-25 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_audit_creation_date             2015-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 Br O2'
_chemical_formula_sum            'C15 H13 Br O2'
_chemical_formula_weight         305.16
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br 0.1811 1.6452 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   6.1506(18)
_cell_length_b                   7.564(2)
_cell_length_c                   28.362(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1319.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1597
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.12
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.669
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_correction_T_min  0.3888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1823 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.5224.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        18.180
_diffrn_reflns_theta_max         18.180
_diffrn_reflns_theta_min         2.199
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms Ag'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1624
_reflns_number_total             1902
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 552 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.003
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0739
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.48838(12) -0.37213(9) -0.23574(2) 0.0285(2) Uani 1 1 d . . . . .
O1 O -0.5228(8) -1.1255(6) 0.00333(14) 0.0402(13) Uani 1 1 d . . . . .
C2 C -0.0191(12) -0.7178(8) -0.18911(18) 0.0181(14) Uani 1 1 d . . . . .
H2 H 0.1194 -0.7567 -0.1997 0.022 Uiso 1 1 calc R . . . .
C3 C 0.0039(11) -0.9079(7) -0.06950(17) 0.0155(14) Uani 1 1 d . . . . .
C4 C -0.1433(10) -0.9915(8) -0.0435(2) 0.0164(16) Uani 1 1 d . . . . .
H4 H -0.1486 -0.9692 -0.0106 0.020 Uiso 1 1 calc R . . . .
C5 C 0.1507(11) -0.7833(10) -0.0465(2) 0.0219(17) Uani 1 1 d . . . . .
H5 H 0.1358 -0.7675 -0.0135 0.026 Uiso 1 1 calc R . . . .
C6 C 0.0138(12) -0.9343(8) -0.12242(17) 0.0172(14) Uani 1 1 d . . . . .
H6 H 0.1701 -0.9297 -0.1320 0.021 Uiso 1 1 calc R . . . .
C7 C -0.1031(10) -0.7881(8) -0.1479(2) 0.0163(16) Uani 1 1 d . . . . .
O8 O 0.2894(8) -0.6988(7) -0.06634(14) 0.0299(13) Uani 1 1 d . . . . .
C9 C -0.4758(12) -1.1805(9) -0.0350(2) 0.0329(18) Uani 1 1 d . . . . .
H9 H -0.5620 -1.2734 -0.0476 0.039 Uiso 1 1 calc R . . . .
C10 C -0.3053(11) -0.7277(9) -0.1332(2) 0.0180(16) Uani 1 1 d . . . . .
H10 H -0.3659 -0.7723 -0.1048 0.022 Uiso 1 1 calc R . . . .
C12 C -0.4197(9) -0.6050(8) -0.15887(19) 0.0155(15) Uani 1 1 d . . . . .
H12 H -0.5587 -0.5661 -0.1486 0.019 Uiso 1 1 calc R . . . .
C13 C -0.2676(11) -1.1703(9) -0.1078(2) 0.0240(18) Uani 1 1 d . . . . .
H13 H -0.3739 -1.2451 -0.1217 0.029 Uiso 1 1 calc R . . . .
C14 C -0.1288(10) -0.5939(9) -0.2152(2) 0.0176(17) Uani 1 1 d . . . . .
H14 H -0.0672 -0.5473 -0.2433 0.021 Uiso 1 1 calc R . . . .
C16 C -0.3294(11) -0.5386(9) -0.19998(19) 0.0198(17) Uani 1 1 d . . . . .
C17 C -0.2958(10) -1.1154(9) -0.0638(2) 0.0201(16) Uani 1 1 d . . . . .
C18 C -0.0746(10) -1.1180(9) -0.1360(2) 0.0241(17) Uani 1 1 d . . . . .
H18 H -0.1185 -1.1141 -0.1700 0.029 Uiso 1 1 calc R . . . .
C21 C 0.0967(12) -1.2634(10) -0.1302(2) 0.036(2) Uani 1 1 d . . . . .
H21A H 0.2237 -1.2356 -0.1497 0.054 Uiso 1 1 calc GR . . . .
H21B H 0.0353 -1.3770 -0.1402 0.054 Uiso 1 1 calc GR . . . .
H21C H 0.1408 -1.2707 -0.0971 0.054 Uiso 1 1 calc GR . . . .


_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
Br1 C16 1.890(6) . ?
O1 C9 1.200(7) . ?
C2 C7 1.384(8) . ?
C2 C14 1.372(8) . ?
C3 C4 1.327(8) . ?
C3 C5 1.459(9) . ?
C3 C6 1.515(7) . ?
C4 C17 1.446(8) . ?
C5 O8 1.205(8) . ?
C6 C7 1.504(8) . ?
C6 C18 1.541(9) . ?
C7 C10 1.389(8) . ?
C9 C17 1.461(9) . ?
C10 C12 1.374(8) . ?
C12 C16 1.386(8) . ?
C13 C17 1.326(8) . ?
C13 C18 1.485(9) . ?
C14 C16 1.373(8) . ?
C18 C21 1.532(9) . ?

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
C14 C2 C7 122.3(6) . . ?
C4 C3 C5 118.8(5) . . ?
C4 C3 C6 120.9(6) . . ?
C5 C3 C6 120.2(6) . . ?
C3 C4 C17 122.0(6) . . ?
O8 C5 C3 124.9(6) . . ?
C3 C6 C18 110.7(5) . . ?
C7 C6 C3 111.1(5) . . ?
C7 C6 C18 112.0(5) . . ?
C2 C7 C6 120.7(6) . . ?
C2 C7 C10 117.4(6) . . ?
C10 C7 C6 121.7(6) . . ?
O1 C9 C17 124.9(7) . . ?
C12 C10 C7 121.5(6) . . ?
C10 C12 C16 119.0(6) . . ?
C17 C13 C18 121.9(6) . . ?
C2 C14 C16 118.7(6) . . ?
C12 C16 Br1 119.1(5) . . ?
C14 C16 Br1 119.9(5) . . ?
C14 C16 C12 121.0(6) . . ?
C4 C17 C9 119.2(6) . . ?
C13 C17 C4 119.5(6) . . ?
C13 C17 C9 121.3(6) . . ?
C13 C18 C6 112.8(6) . . ?
C13 C18 C21 107.5(6) . . ?
C21 C18 C6 112.2(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
O1 C9 C17 C4 8.3(10) . . . . ?
O1 C9 C17 C13 -172.9(7) . . . . ?
C2 C7 C10 C12 1.0(9) . . . . ?
C2 C14 C16 Br1 -178.6(4) . . . . ?
C2 C14 C16 C12 0.5(9) . . . . ?
C3 C4 C17 C9 -170.0(6) . . . . ?
C3 C4 C17 C13 11.2(10) . . . . ?
C3 C6 C7 C2 140.3(6) . . . . ?
C3 C6 C7 C10 -44.6(8) . . . . ?
C3 C6 C18 C13 39.4(8) . . . . ?
C3 C6 C18 C21 -82.2(7) . . . . ?
C4 C3 C5 O8 -179.4(7) . . . . ?
C4 C3 C6 C7 97.6(7) . . . . ?
C4 C3 C6 C18 -27.4(9) . . . . ?
C5 C3 C4 C17 179.3(6) . . . . ?
C5 C3 C6 C7 -79.6(8) . . . . ?
C5 C3 C6 C18 155.4(6) . . . . ?
C6 C3 C4 C17 2.1(9) . . . . ?
C6 C3 C5 O8 -2.2(10) . . . . ?
C6 C7 C10 C12 -174.3(6) . . . . ?
C7 C2 C14 C16 -0.3(9) . . . . ?
C7 C6 C18 C13 -85.1(6) . . . . ?
C7 C6 C18 C21 153.3(5) . . . . ?
C7 C10 C12 C16 -0.8(9) . . . . ?
C10 C12 C16 Br1 179.1(5) . . . . ?
C10 C12 C16 C14 0.1(9) . . . . ?
C14 C2 C7 C6 175.0(5) . . . . ?
C14 C2 C7 C10 -0.4(9) . . . . ?
C17 C13 C18 C6 -30.3(9) . . . . ?
C17 C13 C18 C21 93.9(8) . . . . ?
C18 C6 C7 C2 -95.5(7) . . . . ?
C18 C6 C7 C10 79.7(7) . . . . ?
C18 C13 C17 C4 4.4(10) . . . . ?
C18 C13 C17 C9 -174.3(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_2648
_database_code_depnum_ccdc_archive 'CCDC 1419566'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_audit_creation_date             2015-07-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C20 H24 O3'
_chemical_formula_sum            'C20 H24 O3'
_chemical_formula_weight         312.41
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         C20H24O3
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   8.6911(5)
_cell_length_b                   9.1112(4)
_cell_length_c                   21.5901(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1709.64(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4024
_cell_measurement_temperature    100.01(16)
_cell_measurement_theta_max      21.6580
_cell_measurement_theta_min      2.4900
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2137
_exptl_crystal_F_000             672.3406
_diffrn_reflns_av_R_equivalents  0.1353
_diffrn_reflns_av_unetI/netI     0.1716
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32900
_diffrn_reflns_theta_full        32.7898
_diffrn_reflns_theta_max         32.79
_diffrn_reflns_theta_min         2.43
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9373
_diffrn_measured_fraction_theta_max 0.9348
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   34.00  106.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5695 -178.0000  -90.0000 72

#__ type_ start__ end____ width___ exp.time_
  2 omega  -54.00   47.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5695  -57.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega -100.00   21.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  -19.0000   90.0000 121

#__ type_ start__ end____ width___ exp.time_
  4 omega  -14.00   95.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5695   77.0000    0.0000 109

#__ type_ start__ end____ width___ exp.time_
  5 omega  -54.00   41.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5695  -57.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
  6 omega  -48.00   53.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633   57.0000   90.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0704116000
_diffrn_orient_matrix_UB_12      -0.0325118000
_diffrn_orient_matrix_UB_13      0.0093798000
_diffrn_orient_matrix_UB_21      -0.0381354000
_diffrn_orient_matrix_UB_22      0.0680685000
_diffrn_orient_matrix_UB_23      -0.0042802000
_diffrn_orient_matrix_UB_31      -0.0159520000
_diffrn_orient_matrix_UB_32      -0.0191569000
_diffrn_orient_matrix_UB_33      -0.0311867000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.907
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              31
_reflns_limit_l_min              -31
_reflns_number_gt                2787
_reflns_number_total             5923
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.5989
_refine_diff_density_min         -0.6658
_refine_diff_density_rms         0.1560
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -1.7(7)
_refine_ls_d_res_high            0.6562
_refine_ls_d_res_low             8.3944
_refine_ls_goodness_of_fit_ref   0.9793
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     210
_refine_ls_number_reflns         5923
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1907
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      0.9793
_refine_ls_shift/su_max          0.0129
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.2308
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006), C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00D,H00F), C00K(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C008(H008), C00A(H00A), C00B(H00B), C00J(H00L),
 C00L(H00O), C00M(H00P)
2.d Idealised Me refined as rotating group:
 C00I(H00I,H00J,H00K), C00N(H00Q,H00R,H00S)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O001 O 0.0304(3) 0.4144(2) 0.24406(10) 0.0323(5) Uani 1.000000 .
O002 O 0.6391(3) 0.8617(2) 0.35954(11) 0.0375(6) Uani 1.000000 .
O003 O 0.7778(3) 0.6972(2) 0.29921(11) 0.0386(6) Uani 1.000000 .
C004 C 0.4312(4) 0.6971(3) 0.33676(15) 0.0291(7) Uani 1.000000 .
C005 C 0.0838(4) 0.5296(3) 0.26450(14) 0.0293(7) Uani 1.000000 .
C006 C 0.7403(4) 0.7347(3) 0.35941(15) 0.0325(7) Uani 1.000000 .
C007 C 0.2797(4) 0.6766(3) 0.31191(14) 0.0298(7) Uani 1.000000 .
C008 C 0.4923(4) 0.8318(4) 0.34215(15) 0.0334(7) Uani 1.000000 .
C009 C 0.2165(4) 0.5410(3) 0.30554(14) 0.0282(7) Uani 1.000000 .
C00A C 0.1425(4) 0.1668(3) 0.35801(15) 0.0343(8) Uani 1.000000 .
C00B C 0.0723(4) 0.3834(4) 0.41313(14) 0.0341(8) Uani 1.000000 .
C00C C 0.5258(4) 0.5614(3) 0.34987(14) 0.0267(7) Uani 1.000000 .
C00D C 0.1635(4) 0.3158(3) 0.36830(14) 0.0292(7) Uani 1.000000 .
C00E C 0.2856(4) 0.4037(3) 0.33349(14) 0.0269(7) Uani 1.000000 .
C00F C 0.5157(4) 0.2983(3) 0.39160(15) 0.0304(7) Uani 1.000000 .
C00G C 0.6641(4) 0.6040(3) 0.39043(14) 0.0287(7) Uani 1.000000 .
C00H C 0.4234(4) 0.4386(3) 0.37680(14) 0.0273(7) Uani 1.000000 .
C00I C 0.6086(4) 0.2355(3) 0.33764(16) 0.0358(8) Uani 1.000000 .
C00J C -0.0568(4) 0.1558(4) 0.43450(17) 0.0450(10) Uani 1.000000 .
C00K C 0.6216(4) 0.6376(4) 0.45788(14) 0.0366(8) Uani 1.000000 .
C00L C 0.0329(5) 0.0872(4) 0.39095(16) 0.0432(9) Uani 1.000000 .
C00M C -0.0374(4) 0.3054(4) 0.44580(17) 0.0403(9) Uani 1.000000 .
C00N C 0.7530(5) 0.6937(4) 0.49802(16) 0.0453(10) Uani 1.000000 .
H00B H 0.0855(4) 0.4829(4) 0.42121(14) 0.0409(9) Uiso 1.000000 R
H00p H -0.0980(4) 0.3525(4) 0.47520(17) 0.0483(10) Uiso 1.000000 R
H00l H -0.1303(4) 0.1028(4) 0.45640(17) 0.0540(11) Uiso 1.000000 R
H00o H 0.0204(5) -0.0126(4) 0.38343(16) 0.0518(11) Uiso 1.000000 R
H00A H 0.2027(4) 0.1192(3) 0.32859(15) 0.0412(9) Uiso 1.000000 R
H003 H 0.832(4) 0.762(2) 0.2840(7) 0.0579(9) Uiso 1.000000 GR
H005 H 0.0356(4) 0.6165(3) 0.25286(14) 0.0352(9) Uiso 1.000000 R
H006 H 0.8348(4) 0.7592(3) 0.38193(15) 0.0390(9) Uiso 1.000000 R
H007 H 0.2231(4) 0.7583(3) 0.29982(14) 0.0357(8) Uiso 1.000000 R
H008 H 0.4288(4) 0.9112(4) 0.33324(15) 0.0401(9) Uiso 1.000000 R
H00C H 0.5664(4) 0.5262(3) 0.31020(14) 0.0320(8) Uiso 1.000000 R
H00E H 0.3238(4) 0.3426(3) 0.29948(14) 0.0323(8) Uiso 1.000000 R
H00d H 0.5858(4) 0.3195(3) 0.42540(15) 0.0365(9) Uiso 1.000000 R
H00f H 0.4446(4) 0.2235(3) 0.40591(15) 0.0365(9) Uiso 1.000000 R
H00G H 0.7372(4) 0.5221(3) 0.39022(14) 0.0344(8) Uiso 1.000000 R
H00H H 0.3809(4) 0.4749(3) 0.41594(14) 0.0328(8) Uiso 1.000000 R
H00i H 0.5411(6) 0.215(2) 0.3035(4) 0.0538(12) Uiso 1.000000 GR
H00j H 0.6852(18) 0.3053(11) 0.3251(7) 0.0538(12) Uiso 1.000000 GR
H00k H 0.658(2) 0.1462(14) 0.3505(4) 0.0538(12) Uiso 1.000000 GR
H00m H 0.5401(4) 0.7102(4) 0.45809(14) 0.0439(10) Uiso 1.000000 R
H00n H 0.5810(4) 0.5489(4) 0.47657(14) 0.0439(10) Uiso 1.000000 R
H00q H 0.780(2) 0.7914(11) 0.4854(8) 0.0679(14) Uiso 1.000000 GR
H00r H 0.7213(11) 0.695(3) 0.5406(2) 0.0679(14) Uiso 1.000000 GR
H00s H 0.8406(11) 0.6304(16) 0.4934(9) 0.0679(14) Uiso 1.000000 GR


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
O001 C005 1.230(4) . ?
O002 C006 1.453(4) . ?
O002 C008 1.358(4) . ?
O003 C006 1.383(4) . ?
O003 H003 0.8200 . ?
C004 C007 1.434(4) . ?
C004 C008 1.342(4) . ?
C004 C00C 1.512(4) . ?
C005 C009 1.458(4) . ?
C005 H005 0.9300 . ?
C006 C00G 1.518(4) . ?
C006 H006 0.9800 . ?
C007 C009 1.359(4) . ?
C007 H007 0.9300 . ?
C008 H008 0.9300 . ?
C009 C00E 1.513(4) . ?
C00A C00D 1.388(4) . ?
C00A C00L 1.392(5) . ?
C00A H00A 0.9300 . ?
C00B C00D 1.394(5) . ?
C00B C00M 1.382(5) . ?
C00B H00B 0.9300 . ?
C00C C00G 1.537(4) . ?
C00C C00H 1.544(4) . ?
C00C H00C 0.9800 . ?
C00D C00E 1.527(4) . ?
C00E C00H 1.552(4) . ?
C00E H00E 0.9800 . ?
C00F C00H 1.543(4) . ?
C00F C00I 1.529(5) . ?
C00F H00d 0.9700 . ?
C00F H00f 0.9700 . ?
C00G C00K 1.533(4) . ?
C00G H00G 0.9800 . ?
C00H H00H 0.9800 . ?
C00I H00i 0.9600 . ?
C00I H00j 0.9600 . ?
C00I H00k 0.9600 . ?
C00J C00L 1.372(5) . ?
C00J C00M 1.395(5) . ?
C00J H00l 0.9300 . ?
C00K C00N 1.522(5) . ?
C00K H00m 0.9700 . ?
C00K H00n 0.9700 . ?
C00L H00o 0.9300 . ?
C00M H00p 0.9300 . ?
C00N H00q 0.9600 . ?
C00N H00r 0.9600 . ?
C00N H00s 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 O002 C006 114.1(2) . . ?
H003 O003 C006 109.5 . . ?
C008 C004 C007 121.0(3) . . ?
C00C C004 C007 117.6(3) . . ?
C00C C004 C008 121.1(3) . . ?
C009 C005 O001 125.3(3) . . ?
H005 C005 O001 117.37(18) . . ?
H005 C005 C009 117.37(17) . . ?
O003 C006 O002 110.0(3) . . ?
C00G C006 O002 111.1(3) . . ?
C00G C006 O003 108.8(3) . . ?
H006 C006 O002 108.97(16) . . ?
H006 C006 O003 108.97(19) . . ?
H006 C006 C00G 108.97(17) . . ?
C009 C007 C004 121.8(3) . . ?
H007 C007 C004 119.08(17) . . ?
H007 C007 C009 119.08(19) . . ?
C004 C008 O002 125.3(3) . . ?
H008 C008 O002 117.33(17) . . ?
H008 C008 C004 117.3(2) . . ?
C007 C009 C005 116.5(3) . . ?
C00E C009 C005 119.8(3) . . ?
C00E C009 C007 123.4(3) . . ?
C00L C00A C00D 121.2(4) . . ?
H00A C00A C00D 119.4(2) . . ?
H00A C00A C00L 119.4(2) . . ?
C00M C00B C00D 121.3(3) . . ?
H00B C00B C00D 119.36(19) . . ?
H00B C00B C00M 119.4(2) . . ?
C00G C00C C004 109.0(2) . . ?
C00H C00C C004 110.5(3) . . ?
C00H C00C C00G 114.8(2) . . ?
H00C C00C C004 107.42(17) . . ?
H00C C00C C00G 107.42(16) . . ?
H00C C00C C00H 107.42(16) . . ?
C00B C00D C00A 117.9(3) . . ?
C00E C00D C00A 121.7(3) . . ?
C00E C00D C00B 120.3(3) . . ?
C00D C00E C009 110.7(3) . . ?
C00H C00E C009 112.2(2) . . ?
C00H C00E C00D 110.3(2) . . ?
H00E C00E C009 107.82(16) . . ?
H00E C00E C00D 107.82(17) . . ?
H00E C00E C00H 107.82(16) . . ?
C00I C00F C00H 115.3(3) . . ?
H00d C00F C00H 108.45(16) . . ?
H00d C00F C00I 108.45(18) . . ?
H00f C00F C00H 108.45(17) . . ?
H00f C00F C00I 108.45(17) . . ?
H00f C00F H00d 107.5 . . ?
C00C C00G C006 106.7(2) . . ?
C00K C00G C006 111.6(3) . . ?
C00K C00G C00C 113.8(3) . . ?
H00G C00G C006 108.19(17) . . ?
H00G C00G C00C 108.19(16) . . ?
H00G C00G C00K 108.19(18) . . ?
C00E C00H C00C 111.5(2) . . ?
C00F C00H C00C 112.3(3) . . ?
C00F C00H C00E 110.9(2) . . ?
H00H C00H C00C 107.30(16) . . ?
H00H C00H C00E 107.30(16) . . ?
H00H C00H C00F 107.30(17) . . ?
H00i C00I C00F 109.5 . . ?
H00j C00I C00F 109.5 . . ?
H00j C00I H00i 109.5 . . ?
H00k C00I C00F 109.5 . . ?
H00k C00I H00i 109.5 . . ?
H00k C00I H00j 109.5 . . ?
C00M C00J C00L 119.7(3) . . ?
H00l C00J C00L 120.1(2) . . ?
H00l C00J C00M 120.1(2) . . ?
C00N C00K C00G 115.3(3) . . ?
H00m C00K C00G 108.45(18) . . ?
H00m C00K C00N 108.5(2) . . ?
H00n C00K C00G 108.45(18) . . ?
H00n C00K C00N 108.5(2) . . ?
H00n C00K H00m 107.5 . . ?
C00J C00L C00A 120.1(4) . . ?
H00o C00L C00A 119.9(2) . . ?
H00o C00L C00J 119.9(2) . . ?
C00J C00M C00B 119.8(4) . . ?
H00p C00M C00B 120.1(2) . . ?
H00p C00M C00J 120.1(2) . . ?
H00q C00N C00K 109.5 . . ?
H00r C00N C00K 109.5 . . ?
H00r C00N H00q 109.5 . . ?
H00s C00N C00K 109.5 . . ?
H00s C00N H00q 109.5 . . ?
H00s C00N H00r 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_colour            yellowish
_exptl_crystal_description       block
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane/ethylacetate'
####################################################################### 
# 
# 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_exp_2662
_database_code_depnum_ccdc_archive 'CCDC 1419567'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_audit_creation_date             2015-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 O2'
_chemical_formula_sum            'C12 H10 O2'
_chemical_formula_weight         186.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H10O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.0175(4)
_cell_length_b                   11.1406(6)
_cell_length_c                   11.9874(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     937.18(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2852
_cell_measurement_temperature    110(14)
_cell_measurement_theta_max      26.9320
_cell_measurement_theta_min      3.3350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7396
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.319
_diffrn_reflns_theta_min         2.496
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       10.3194   77.0000   60.0000 108

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   65.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4132   77.0000  -30.0000 109

#__ type_ start__ end____ width___ exp.time_
  3 omega   34.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       10.3194 -178.0000  -60.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0662305000
_diffrn_orient_matrix_UB_12      0.0313008000
_diffrn_orient_matrix_UB_13      0.0339228000
_diffrn_orient_matrix_UB_21      0.0761262000
_diffrn_orient_matrix_UB_22      -0.0236070000
_diffrn_orient_matrix_UB_23      -0.0321433000
_diffrn_orient_matrix_UB_31      -0.0055352000
_diffrn_orient_matrix_UB_32      0.0501685000
_diffrn_orient_matrix_UB_33      -0.0363076000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.617
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                1766
_reflns_number_total             2232
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 579 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.3150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1312
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C005(H005), C006(H006), C007(H007), C008(H008), C009(H009),
 C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.5885(3) 0.49506(19) 0.79060(17) 0.0304(5) Uani 1 1 d . . . . .
O002 O 0.6298(4) 0.80506(19) 0.50906(17) 0.0310(6) Uani 1 1 d . . . . .
C003 C 0.5835(4) 0.2248(2) 0.4664(2) 0.0198(6) Uani 1 1 d . . . . .
C004 C 0.5745(4) 0.2719(2) 0.5795(2) 0.0202(6) Uani 1 1 d . . . . .
H004 H 0.5490 0.2152 0.6344 0.024 Uiso 1 1 calc R . . . .
C005 C 0.6233(4) 0.0492(3) 0.3484(3) 0.0243(7) Uani 1 1 d . . . . .
H005 H 0.6424 -0.0330 0.3413 0.029 Uiso 1 1 calc R . . . .
C006 C 0.5984(5) 0.6031(2) 0.5689(2) 0.0219(6) Uani 1 1 d . . . . .
H006 H 0.5174 0.6208 0.6281 0.026 Uiso 1 1 calc R . . . .
C007 C 0.6101(4) 0.1004(2) 0.4534(2) 0.0222(6) Uani 1 1 d . . . . .
H007 H 0.6188 0.0517 0.5163 0.027 Uiso 1 1 calc R . . . .
C008 C 0.6687(5) 0.6990(3) 0.4976(2) 0.0233(7) Uani 1 1 d . . . . .
H008 H 0.7490 0.6780 0.4390 0.028 Uiso 1 1 calc R . . . .
C009 C 0.5717(5) 0.4023(3) 0.7387(2) 0.0244(7) Uani 1 1 d . . . . .
H009 H 0.5393 0.3342 0.7794 0.029 Uiso 1 1 calc R . . . .
C00A C 0.6502(4) 0.4895(3) 0.5495(2) 0.0201(6) Uani 1 1 d . . . . .
H00A H 0.7264 0.4753 0.4875 0.024 Uiso 1 1 calc R . . . .
C00B C 0.5786(4) 0.2431(3) 0.2650(2) 0.0238(6) Uani 1 1 d . . . . .
H00B H 0.5682 0.2910 0.2017 0.029 Uiso 1 1 calc R . . . .
C00C C 0.5644(4) 0.2946(3) 0.3700(2) 0.0218(6) Uani 1 1 d . . . . .
H00C H 0.5419 0.3766 0.3764 0.026 Uiso 1 1 calc R . . . .
C00D C 0.5974(4) 0.3861(2) 0.6174(2) 0.0204(6) Uani 1 1 d . . . . .
C00E C 0.6085(5) 0.1199(3) 0.2539(2) 0.0246(7) Uani 1 1 d . . . . .
H00E H 0.6183 0.0855 0.1834 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C009 1.213(4) . ?
O002 C008 1.220(3) . ?
C003 C004 1.455(4) . ?
C003 C007 1.407(4) . ?
C003 C00C 1.400(4) . ?
C004 H004 0.9300 . ?
C004 C00D 1.360(4) . ?
C005 H005 0.9300 . ?
C005 C007 1.385(4) . ?
C005 C00E 1.384(4) . ?
C006 H006 0.9300 . ?
C006 C008 1.455(4) . ?
C006 C00A 1.337(4) . ?
C007 H007 0.9300 . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?
C009 C00D 1.476(4) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.458(4) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.387(4) . ?
C00B C00E 1.395(4) . ?
C00C H00C 0.9300 . ?
C00E H00E 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 C003 C004 117.7(3) . . ?
C00C C003 C004 124.4(2) . . ?
C00C C003 C007 117.9(3) . . ?
C003 C004 H004 115.0 . . ?
C00D C004 C003 130.1(3) . . ?
C00D C004 H004 115.0 . . ?
C007 C005 H005 119.8 . . ?
C00E C005 H005 119.8 . . ?
C00E C005 C007 120.3(3) . . ?
C008 C006 H006 120.0 . . ?
C00A C006 H006 120.0 . . ?
C00A C006 C008 120.0(3) . . ?
C003 C007 H007 119.5 . . ?
C005 C007 C003 121.0(3) . . ?
C005 C007 H007 119.5 . . ?
O002 C008 C006 124.7(3) . . ?
O002 C008 H008 117.7 . . ?
C006 C008 H008 117.7 . . ?
O001 C009 H009 116.6 . . ?
O001 C009 C00D 126.7(3) . . ?
C00D C009 H009 116.6 . . ?
C006 C00A H00A 117.2 . . ?
C006 C00A C00D 125.6(3) . . ?
C00D C00A H00A 117.2 . . ?
C00C C00B H00B 119.9 . . ?
C00C C00B C00E 120.3(3) . . ?
C00E C00B H00B 119.9 . . ?
C003 C00C H00C 119.6 . . ?
C00B C00C C003 120.9(3) . . ?
C00B C00C H00C 119.6 . . ?
C004 C00D C009 115.4(3) . . ?
C004 C00D C00A 125.6(3) . . ?
C00A C00D C009 119.0(3) . . ?
C005 C00E C00B 119.5(3) . . ?
C005 C00E H00E 120.2 . . ?
C00B C00E H00E 120.2 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane/ethylacetate'
