# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_17MCD007
_database_code_depnum_ccdc_archive 'CCDC 1964184'
loop_
_audit_author_name
_audit_author_address
'Lopez F'
;CSIC and USC
Spain
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;

_audit_creation_date             2017-03-26
_computing_data_collection       'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_cell_oxdiff_length_a            6.2162(5)
_cell_oxdiff_length_b            12.5583(7)
_cell_oxdiff_length_c            20.7881(12)
_cell_oxdiff_angle_alpha         92.381(5)
_cell_oxdiff_angle_beta          98.293(6)
_cell_oxdiff_angle_gamma         100.115(6)
_cell_oxdiff_volume              1577.18(18)
_cell_oxdiff_measurement_reflns_used 2495
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 -11 0.0114
4 -4 -3 0.0645
-4 4 3 0.0645
-1 -7 -3 0.0018
1 7 3 0.0048
0 -5 11 0.0034
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0014 4.9957 -10.9920 0.0389 -0.3070 0.9507
3.9978 -3.9993 -2.9879 0.0814 -0.9479 -0.4360
-3.9978 3.9993 2.9879 -0.0814 0.9479 0.4360
-0.9995 -7.0013 -3.0103 0.9388 0.1431 -0.3249
0.9995 7.0013 3.0103 -0.9388 -0.1431 0.3249
-0.0014 -4.9957 10.9920 -0.0389 0.3070 -0.9507
_exptl_absorpt_correction_T_min  0.85724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.23a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.828
_oxdiff_exptl_absorpt_empirical_full_max 1.279
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_reflns_av_sigmaI/netI    0.1206
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1128312000
_diffrn_orient_matrix_UB_12      -0.0974149000
_diffrn_orient_matrix_UB_13      -0.0478232000
_diffrn_orient_matrix_UB_21      -0.2177761000
_diffrn_orient_matrix_UB_22      -0.0011276000
_diffrn_orient_matrix_UB_23      0.0273905000
_diffrn_orient_matrix_UB_31      -0.0689712000
_diffrn_orient_matrix_UB_32      0.0781671000
_diffrn_orient_matrix_UB_33      -0.0509695000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  24.00   0.50    5.00    --    0.00  19.00  30.00   66
  2  ω     -6.00  64.00   0.50    5.00    --    0.00  57.00  90.00  140
  3  ω     48.00  79.00   0.50    5.00    --    0.00  19.00  30.00   62
  4  ω     41.00  73.00   0.50    5.00    --    0.00  77.00 120.00   64
  5  ω     -7.00  20.00   0.50    5.00    --    0.00  77.00 120.00   54
  6  ω     22.00  54.00   0.50   25.00    --   96.84 -30.00   0.00   64
  7  ω     25.00  59.00   0.50   25.00    --   96.84 -30.00  30.00   68
  8  ω     76.00 112.00   0.50   25.00    --   96.84 -61.00   0.00   72
  9  ω     31.00 116.00   0.50   25.00    --   96.84-125.00-150.00  170
 10  ω     37.00  69.00   0.50   25.00    --   96.84 -61.00   0.00   64
 11  ω     38.00 118.00   0.50   25.00    --   96.84 -77.00 -60.00  160
 12  ω     25.00  56.00   0.50   25.00    --   96.84 -30.00-120.00   62
 13  ω     19.00  56.00   0.50   25.00    --   96.84 -30.00 -60.00   74
 14  ω     19.00  55.00   0.50   25.00    --   96.84 -30.00 -30.00   72
 15  ω     22.00 107.00   0.50   25.00    --   96.84 -94.00 -60.00  170
 16  ω     24.00 106.00   0.50   25.00    --   96.84 -94.00-120.00  164
 17  ω     21.00  95.00   0.50   25.00    --   96.84 -94.00-150.00  148
 18  ω     18.00 148.00   0.50   25.00    --   96.84   0.00-180.00  260
 19  ω     20.00  52.00   0.50   25.00    --   96.84 -30.00  90.00   64
 20  ω   -101.00 -28.00   0.50   25.00    --  -84.25  77.00 120.00  146
 21  ω   -145.00 -71.00   0.50   25.00    --  -84.25 -61.00-150.00  148
;
_diffrn_measurement_method       'ω scans'
_diffrn_oxdiff_ac3_digest_frames 
;
01d08591a90e910b76e79a58123b74ba5302292efc4
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01f94e75c0f56d3e793ede73c770d009143d7f
;
_reflns_odcompleteness_completeness 98.10
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1
_chemical_oxdiff_formula         'C12 H18 O1'

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 O '
_chemical_formula_sum            'C12 H18 O '
_chemical_formula_weight         178.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2162(5)
_cell_length_b                   12.5583(8)
_cell_length_c                   20.7881(12)
_cell_angle_alpha                92.381(5)
_cell_angle_beta                 98.293(6)
_cell_angle_gamma                100.115(6)
_cell_volume                     1577.16(19)
_cell_formula_units_Z            6
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    2495
_cell_measurement_theta_min      4.2900
_cell_measurement_theta_max      71.3840

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.018
_exptl_crystal_size_min          0.007
_exptl_absorpt_coefficient_mu    0.531
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_special_details   ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12485
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.584
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_full        67.055
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             5534
_reflns_number_gt                3322
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0677P)²+0.0455P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5534
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6456(4) 0.7409(2) 0.34347(12) 0.0288(6) Uani 1 1 d . . . . .
H1 H 0.5669 0.7988 0.3574 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8516(4) 0.7407(2) 0.39255(12) 0.0271(6) Uani 1 1 d . . . . .
H2 H 0.9336 0.6893 0.3727 0.032 Uiso 1 1 calc R U . . .
C3 C 1.0242(4) 0.8384(2) 0.41929(12) 0.0286(6) Uani 1 1 d . . . . .
C4 C 1.2092(5) 0.8037(3) 0.46527(14) 0.0395(7) Uani 1 1 d . . . . .
H4A H 1.3249 0.7890 0.4398 0.047 Uiso 1 1 calc R U . . .
H4B H 1.2765 0.8647 0.4977 0.047 Uiso 1 1 calc R U . . .
C5 C 1.1382(5) 0.7050(3) 0.50108(13) 0.0398(8) Uani 1 1 d . . . . .
H5 H 1.2485 0.6802 0.5301 0.048 Uiso 1 1 calc R U . . .
C6 C 0.9342(5) 0.6506(3) 0.49509(13) 0.0386(7) Uani 1 1 d . . . . .
H6 H 0.9015 0.5910 0.5209 0.046 Uiso 1 1 calc R U . . .
C7 C 0.7540(5) 0.6814(2) 0.44829(12) 0.0307(6) Uani 1 1 d . . . . .
H7 H 0.6796 0.7319 0.4719 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5774(5) 0.5888(2) 0.41357(13) 0.0370(7) Uani 1 1 d . . . . .
H8A H 0.4521 0.5732 0.4383 0.044 Uiso 1 1 calc R U . . .
H8B H 0.6398 0.5222 0.4086 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5016(5) 0.6288(2) 0.34665(14) 0.0365(7) Uani 1 1 d . . . . .
H9A H 0.3434 0.6345 0.3419 0.044 Uiso 1 1 calc R U . . .
H9B H 0.5220 0.5779 0.3113 0.044 Uiso 1 1 calc R U . . .
O10 O 0.7024(3) 0.75961(15) 0.28043(9) 0.0301(4) Uani 1 1 d . . . . .
H10 H 0.579(5) 0.758(2) 0.2518(11) 0.045 Uiso 1 1 calc R U . . .
C11 C 1.0338(5) 0.9431(2) 0.40712(13) 0.0328(6) Uani 1 1 d . . . . .
C12 C 0.8641(5) 0.9889(2) 0.36256(14) 0.0390(7) Uani 1 1 d . . . . .
H12A H 0.9391 1.0400 0.3350 0.059 Uiso 1 1 calc R U . . .
H12B H 0.7779 1.0267 0.3887 0.059 Uiso 1 1 calc R U . . .
H12C H 0.7650 0.9298 0.3350 0.059 Uiso 1 1 calc R U . . .
C13 C 1.2243(6) 1.0309(3) 0.43772(15) 0.0460(8) Uani 1 1 d . . . . .
H13A H 1.3147 1.0564 0.4046 0.069 Uiso 0.45(3) 1 calc R U P . .
H13B H 1.3152 1.0016 0.4727 0.069 Uiso 0.45(3) 1 calc R U P . .
H13C H 1.1664 1.0915 0.4557 0.069 Uiso 0.45(3) 1 calc R U P . .
H13D H 1.2162 1.0432 0.4841 0.069 Uiso 0.55(3) 1 calc R U P . .
H13E H 1.2157 1.0981 0.4160 0.069 Uiso 0.55(3) 1 calc R U P . .
H13F H 1.3645 1.0081 0.4330 0.069 Uiso 0.55(3) 1 calc R U P . .
C21 C 0.2940(5) 0.8679(2) 0.18280(13) 0.0300(6) Uani 1 1 d . . . . .
H21 H 0.1782 0.8627 0.1435 0.036 Uiso 1 1 calc R U . . .
C22 C 0.5020(4) 0.9428(2) 0.17160(12) 0.0258(6) Uani 1 1 d . . . . .
H22 H 0.6195 0.9326 0.2079 0.031 Uiso 1 1 calc R U . . .
C23 C 0.6060(4) 0.9401(2) 0.11011(13) 0.0298(6) Uani 1 1 d . . . . .
C24 C 0.8050(5) 1.0327(2) 0.11348(15) 0.0403(7) Uani 1 1 d . . . . .
H24A H 0.9413 1.0029 0.1257 0.048 Uiso 1 1 calc R U . . .
H24B H 0.8082 1.0588 0.0693 0.048 Uiso 1 1 calc R U . . .
C25 C 0.8120(5) 1.1273(2) 0.15929(14) 0.0376(7) Uani 1 1 d . . . . .
H25 H 0.9418 1.1817 0.1659 0.045 Uiso 1 1 calc R U . . .
C26 C 0.6496(5) 1.1412(2) 0.19164(14) 0.0362(7) Uani 1 1 d . . . . .
H26 H 0.6615 1.2061 0.2181 0.043 Uiso 1 1 calc R U . . .
C27 C 0.4484(5) 1.0556(2) 0.18673(13) 0.0297(6) Uani 1 1 d . . . . .
H27 H 0.3366 1.0709 0.1503 0.036 Uiso 1 1 calc R U . . .
C28 C 0.3379(5) 1.0399(2) 0.24745(13) 0.0347(7) Uani 1 1 d . . . . .
H28A H 0.4498 1.0538 0.2873 0.042 Uiso 1 1 calc R U . . .
H28B H 0.2320 1.0898 0.2497 0.042 Uiso 1 1 calc R U . . .
C29 C 0.2181(6) 0.9226(2) 0.24101(14) 0.0408(7) Uani 1 1 d . . . . .
H29A H 0.0559 0.9189 0.2330 0.049 Uiso 1 1 calc R U . . .
H29B H 0.2569 0.8863 0.2813 0.049 Uiso 1 1 calc R U . . .
O30 O 0.3383(3) 0.76139(14) 0.19597(9) 0.0302(4) Uani 1 1 d . . . . .
H30 H 0.220(5) 0.7218(17) 0.2130(15) 0.045 Uiso 1 1 calc R U . . .
C31 C 0.5521(5) 0.8687(2) 0.05787(13) 0.0363(7) Uani 1 1 d . . . . .
C32 C 0.3677(6) 0.7720(3) 0.04696(15) 0.0458(8) Uani 1 1 d . . . . .
H32A H 0.2465 0.7875 0.0152 0.069 Uiso 1 1 calc R U . . .
H32B H 0.3141 0.7561 0.0882 0.069 Uiso 1 1 calc R U . . .
H32C H 0.4222 0.7092 0.0303 0.069 Uiso 1 1 calc R U . . .
C33 C 0.6842(7) 0.8786(3) 0.00165(16) 0.0555(9) Uani 1 1 d . . . . .
H33A H 0.8400 0.9076 0.0185 0.083 Uiso 0.42(4) 1 calc R U P . .
H33B H 0.6266 0.9276 -0.0291 0.083 Uiso 0.42(4) 1 calc R U P . .
H33C H 0.6713 0.8069 -0.0207 0.083 Uiso 0.42(4) 1 calc R U P . .
H33D H 0.5852 0.8539 -0.0393 0.083 Uiso 0.58(4) 1 calc R U P . .
H33E H 0.7987 0.8338 0.0082 0.083 Uiso 0.58(4) 1 calc R U P . .
H33F H 0.7540 0.9545 -0.0002 0.083 Uiso 0.58(4) 1 calc R U P . .
C41 C -0.1164(4) 0.5557(2) 0.19599(12) 0.0272(6) Uani 1 1 d . . . . .
H41 H -0.2384 0.5124 0.2156 0.033 Uiso 1 1 calc R U . . .
C42 C 0.0534(4) 0.4860(2) 0.18435(12) 0.0263(6) Uani 1 1 d . . . . .
H42 H 0.1878 0.5379 0.1770 0.032 Uiso 1 1 calc R U . . .
C43 C 0.1379(4) 0.4080(2) 0.23185(12) 0.0275(6) Uani 1 1 d . . . . .
C44 C 0.3082(5) 0.3540(2) 0.20415(13) 0.0331(7) Uani 1 1 d . . . . .
H44A H 0.4569 0.3967 0.2209 0.040 Uiso 1 1 calc R U . . .
H44B H 0.3018 0.2812 0.2211 0.040 Uiso 1 1 calc R U . . .
C45 C 0.2842(5) 0.3413(2) 0.13144(14) 0.0345(7) Uani 1 1 d . . . . .
H45 H 0.3920 0.3107 0.1127 0.041 Uiso 1 1 calc R U . . .
C46 C 0.1214(5) 0.3703(2) 0.09157(14) 0.0374(7) Uani 1 1 d . . . . .
H46 H 0.1095 0.3551 0.0459 0.045 Uiso 1 1 calc R U . . .
C47 C -0.0434(5) 0.4267(2) 0.11771(12) 0.0325(6) Uani 1 1 d . . . . .
H47 H -0.1764 0.3717 0.1226 0.039 Uiso 1 1 calc R U . . .
C48 C -0.1184(6) 0.5182(2) 0.07883(14) 0.0393(7) Uani 1 1 d . . . . .
H48A H 0.0073 0.5618 0.0619 0.047 Uiso 1 1 calc R U . . .
H48B H -0.2354 0.4886 0.0418 0.047 Uiso 1 1 calc R U . . .
C49 C -0.2074(5) 0.5867(2) 0.12762(13) 0.0374(7) Uani 1 1 d . . . . .
H49A H -0.3712 0.5712 0.1204 0.045 Uiso 1 1 calc R U . . .
H49B H -0.1567 0.6649 0.1230 0.045 Uiso 1 1 calc R U . . .
O50 O -0.0091(3) 0.64775(14) 0.23931(8) 0.0292(4) Uani 1 1 d . . . . .
H50 H -0.125(4) 0.6865(18) 0.2543(13) 0.044 Uiso 1 1 calc R U . . .
C51 C 0.0911(5) 0.3882(2) 0.29133(13) 0.0308(6) Uani 1 1 d . . . . .
C52 C -0.0639(5) 0.4396(2) 0.32658(13) 0.0374(7) Uani 1 1 d . . . . .
H52A H -0.0916 0.5056 0.3059 0.056 Uiso 1 1 calc R U . . .
H52B H 0.0029 0.4579 0.3722 0.056 Uiso 1 1 calc R U . . .
H52C H -0.2039 0.3886 0.3245 0.056 Uiso 1 1 calc R U . . .
C53 C 0.1961(6) 0.3087(3) 0.33270(14) 0.0439(8) Uani 1 1 d . . . . .
H53A H 0.3048 0.3487 0.3682 0.066 Uiso 0.56(4) 1 calc R U P . .
H53B H 0.2700 0.2653 0.3057 0.066 Uiso 0.56(4) 1 calc R U P . .
H53C H 0.0814 0.2607 0.3509 0.066 Uiso 0.56(4) 1 calc R U P . .
H53D H 0.1327 0.2345 0.3150 0.066 Uiso 0.44(4) 1 calc R U P . .
H53E H 0.1675 0.3178 0.3776 0.066 Uiso 0.44(4) 1 calc R U P . .
H53F H 0.3561 0.3224 0.3323 0.066 Uiso 0.44(4) 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O10 1.424(3) . ?
C1 C2 1.519(4) . ?
C1 C9 1.539(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.508(4) . ?
C2 C7 1.543(4) . ?
C2 H2 1.0000 . ?
C3 C11 1.342(4) . ?
C3 C4 1.523(4) . ?
C4 C5 1.504(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.317(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.490(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.526(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.537(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O10 H10 0.90(3) . ?
C11 C12 1.509(4) . ?
C11 C13 1.512(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C21 O30 1.442(3) . ?
C21 C22 1.513(4) . ?
C21 C29 1.539(4) . ?
C21 H21 1.0000 . ?
C22 C23 1.515(4) . ?
C22 C27 1.541(3) . ?
C22 H22 1.0000 . ?
C23 C31 1.343(4) . ?
C23 C24 1.533(4) . ?
C24 C25 1.482(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.323(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.487(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.525(4) . ?
C27 H27 1.0000 . ?
C28 C29 1.520(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
O30 H30 0.94(4) . ?
C31 C32 1.501(4) . ?
C31 C33 1.519(4) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C33 H33D 0.9800 . ?
C33 H33E 0.9800 . ?
C33 H33F 0.9800 . ?
C41 O50 1.436(3) . ?
C41 C42 1.523(4) . ?
C41 C49 1.544(4) . ?
C41 H41 1.0000 . ?
C42 C43 1.523(3) . ?
C42 C47 1.534(4) . ?
C42 H42 1.0000 . ?
C43 C51 1.334(4) . ?
C43 C44 1.520(4) . ?
C44 C45 1.496(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.325(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.493(4) . ?
C46 H46 0.9500 . ?
C47 C48 1.533(4) . ?
C47 H47 1.0000 . ?
C48 C49 1.527(4) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
O50 H50 1.01(3) . ?
C51 C52 1.505(4) . ?
C51 C53 1.517(4) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C53 H53D 0.9800 . ?
C53 H53E 0.9800 . ?
C53 H53F 0.9800 . ?

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
O10 C1 C2 110.5(2) . . ?
O10 C1 C9 113.1(2) . . ?
C2 C1 C9 104.4(2) . . ?
O10 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
C9 C1 H1 109.6 . . ?
C3 C2 C1 126.1(2) . . ?
C3 C2 C7 110.7(2) . . ?
C1 C2 C7 101.8(2) . . ?
C3 C2 H2 105.5 . . ?
C1 C2 H2 105.5 . . ?
C7 C2 H2 105.5 . . ?
C11 C3 C2 129.7(2) . . ?
C11 C3 C4 120.3(3) . . ?
C2 C3 C4 110.0(2) . . ?
C5 C4 C3 114.8(3) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.5 . . ?
C6 C5 C4 124.7(3) . . ?
C6 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 116.7(2) . . ?
C6 C7 C2 110.0(2) . . ?
C8 C7 C2 104.3(2) . . ?
C6 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C2 C7 H7 108.5 . . ?
C7 C8 C9 105.3(2) . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C8 C9 C1 106.5(2) . . ?
C8 C9 H9A 110.4 . . ?
C1 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
C1 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C1 O10 H10 109.5 . . ?
C3 C11 C12 126.0(3) . . ?
C3 C11 C13 122.4(3) . . ?
C12 C11 C13 111.6(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C13 H13D 109.5 . . ?
H13A C13 H13D 141.1 . . ?
H13B C13 H13D 56.3 . . ?
H13C C13 H13D 56.3 . . ?
C11 C13 H13E 109.5 . . ?
H13A C13 H13E 56.3 . . ?
H13B C13 H13E 141.1 . . ?
H13C C13 H13E 56.3 . . ?
H13D C13 H13E 109.5 . . ?
C11 C13 H13F 109.5 . . ?
H13A C13 H13F 56.3 . . ?
H13B C13 H13F 56.3 . . ?
H13C C13 H13F 141.1 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
O30 C21 C22 110.8(2) . . ?
O30 C21 C29 112.0(2) . . ?
C22 C21 C29 105.1(2) . . ?
O30 C21 H21 109.6 . . ?
C22 C21 H21 109.6 . . ?
C29 C21 H21 109.6 . . ?
C21 C22 C23 124.9(2) . . ?
C21 C22 C27 102.2(2) . . ?
C23 C22 C27 111.2(2) . . ?
C21 C22 H22 105.7 . . ?
C23 C22 H22 105.7 . . ?
C27 C22 H22 105.7 . . ?
C31 C23 C22 129.4(3) . . ?
C31 C23 C24 119.6(3) . . ?
C22 C23 C24 110.9(2) . . ?
C25 C24 C23 116.6(2) . . ?
C25 C24 H24A 108.2 . . ?
C23 C24 H24A 108.2 . . ?
C25 C24 H24B 108.2 . . ?
C23 C24 H24B 108.2 . . ?
H24A C24 H24B 107.3 . . ?
C26 C25 C24 124.4(3) . . ?
C26 C25 H25 117.8 . . ?
C24 C25 H25 117.8 . . ?
C25 C26 C27 120.3(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 117.4(2) . . ?
C26 C27 C22 110.9(2) . . ?
C28 C27 C22 102.9(2) . . ?
C26 C27 H27 108.4 . . ?
C28 C27 H27 108.4 . . ?
C22 C27 H27 108.4 . . ?
C29 C28 C27 105.7(2) . . ?
C29 C28 H28A 110.6 . . ?
C27 C28 H28A 110.6 . . ?
C29 C28 H28B 110.6 . . ?
C27 C28 H28B 110.6 . . ?
H28A C28 H28B 108.7 . . ?
C28 C29 C21 106.3(2) . . ?
C28 C29 H29A 110.5 . . ?
C21 C29 H29A 110.5 . . ?
C28 C29 H29B 110.5 . . ?
C21 C29 H29B 110.5 . . ?
H29A C29 H29B 108.7 . . ?
C21 O30 H30 109.5 . . ?
C23 C31 C32 127.0(3) . . ?
C23 C31 C33 121.1(3) . . ?
C32 C31 C33 111.9(3) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C33 H33D 109.5 . . ?
H33A C33 H33D 141.1 . . ?
H33B C33 H33D 56.3 . . ?
H33C C33 H33D 56.3 . . ?
C31 C33 H33E 109.5 . . ?
H33A C33 H33E 56.3 . . ?
H33B C33 H33E 141.1 . . ?
H33C C33 H33E 56.3 . . ?
H33D C33 H33E 109.5 . . ?
C31 C33 H33F 109.5 . . ?
H33A C33 H33F 56.3 . . ?
H33B C33 H33F 56.3 . . ?
H33C C33 H33F 141.1 . . ?
H33D C33 H33F 109.5 . . ?
H33E C33 H33F 109.5 . . ?
O50 C41 C42 108.9(2) . . ?
O50 C41 C49 113.2(2) . . ?
C42 C41 C49 104.9(2) . . ?
O50 C41 H41 109.9 . . ?
C42 C41 H41 109.9 . . ?
C49 C41 H41 109.9 . . ?
C41 C42 C43 124.9(2) . . ?
C41 C42 C47 103.1(2) . . ?
C43 C42 C47 110.7(2) . . ?
C41 C42 H42 105.6 . . ?
C43 C42 H42 105.6 . . ?
C47 C42 H42 105.6 . . ?
C51 C43 C44 120.3(2) . . ?
C51 C43 C42 129.5(2) . . ?
C44 C43 C42 110.0(2) . . ?
C45 C44 C43 116.2(2) . . ?
C45 C44 H44A 108.2 . . ?
C43 C44 H44A 108.2 . . ?
C45 C44 H44B 108.2 . . ?
C43 C44 H44B 108.2 . . ?
H44A C44 H44B 107.4 . . ?
C46 C45 C44 123.9(3) . . ?
C46 C45 H45 118.0 . . ?
C44 C45 H45 118.0 . . ?
C45 C46 C47 120.6(3) . . ?
C45 C46 H46 119.7 . . ?
C47 C46 H46 119.7 . . ?
C46 C47 C48 116.8(2) . . ?
C46 C47 C42 111.0(2) . . ?
C48 C47 C42 101.9(2) . . ?
C46 C47 H47 108.9 . . ?
C48 C47 H47 108.9 . . ?
C42 C47 H47 108.9 . . ?
C49 C48 C47 104.7(2) . . ?
C49 C48 H48A 110.8 . . ?
C47 C48 H48A 110.8 . . ?
C49 C48 H48B 110.8 . . ?
C47 C48 H48B 110.8 . . ?
H48A C48 H48B 108.9 . . ?
C48 C49 C41 106.4(2) . . ?
C48 C49 H49A 110.4 . . ?
C41 C49 H49A 110.4 . . ?
C48 C49 H49B 110.4 . . ?
C41 C49 H49B 110.4 . . ?
H49A C49 H49B 108.6 . . ?
C41 O50 H50 109.5 . . ?
C43 C51 C52 126.5(2) . . ?
C43 C51 C53 122.3(3) . . ?
C52 C51 C53 111.3(2) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C53 H53D 109.5 . . ?
H53A C53 H53D 141.1 . . ?
H53B C53 H53D 56.3 . . ?
H53C C53 H53D 56.3 . . ?
C51 C53 H53E 109.5 . . ?
H53A C53 H53E 56.3 . . ?
H53B C53 H53E 141.1 . . ?
H53C C53 H53E 56.3 . . ?
H53D C53 H53E 109.5 . . ?
C51 C53 H53F 109.5 . . ?
H53A C53 H53F 56.3 . . ?
H53B C53 H53F 56.3 . . ?
H53C C53 H53F 141.1 . . ?
H53D C53 H53F 109.5 . . ?
H53E C53 H53F 109.5 . . ?

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
O10 C1 C2 C3 72.1(3) . . . . ?
C9 C1 C2 C3 -166.0(2) . . . . ?
O10 C1 C2 C7 -161.0(2) . . . . ?
C9 C1 C2 C7 -39.1(2) . . . . ?
C1 C2 C3 C11 0.9(4) . . . . ?
C7 C2 C3 C11 -122.3(3) . . . . ?
C1 C2 C3 C4 -177.8(2) . . . . ?
C7 C2 C3 C4 59.0(3) . . . . ?
C11 C3 C4 C5 150.5(3) . . . . ?
C2 C3 C4 C5 -30.6(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C7 2.9(5) . . . . ?
C5 C6 C7 C8 143.8(3) . . . . ?
C5 C6 C7 C2 25.3(4) . . . . ?
C3 C2 C7 C6 -56.5(3) . . . . ?
C1 C2 C7 C6 167.2(2) . . . . ?
C3 C2 C7 C8 177.6(2) . . . . ?
C1 C2 C7 C8 41.3(2) . . . . ?
C6 C7 C8 C9 -148.8(2) . . . . ?
C2 C7 C8 C9 -27.2(3) . . . . ?
C7 C8 C9 C1 2.9(3) . . . . ?
O10 C1 C9 C8 143.0(2) . . . . ?
C2 C1 C9 C8 22.9(3) . . . . ?
C2 C3 C11 C12 1.0(5) . . . . ?
C4 C3 C11 C12 179.6(3) . . . . ?
C2 C3 C11 C13 -178.7(3) . . . . ?
C4 C3 C11 C13 -0.1(4) . . . . ?
O30 C21 C22 C23 75.3(3) . . . . ?
C29 C21 C22 C23 -163.5(2) . . . . ?
O30 C21 C22 C27 -157.7(2) . . . . ?
C29 C21 C22 C27 -36.5(2) . . . . ?
C21 C22 C23 C31 -6.7(4) . . . . ?
C27 C22 C23 C31 -129.8(3) . . . . ?
C21 C22 C23 C24 175.7(2) . . . . ?
C27 C22 C23 C24 52.6(3) . . . . ?
C31 C23 C24 C25 160.1(2) . . . . ?
C22 C23 C24 C25 -22.0(3) . . . . ?
C23 C24 C25 C26 -7.2(4) . . . . ?
C24 C25 C26 C27 4.0(4) . . . . ?
C25 C26 C27 C28 145.4(3) . . . . ?
C25 C26 C27 C22 27.5(3) . . . . ?
C21 C22 C27 C26 168.5(2) . . . . ?
C23 C22 C27 C26 -56.1(3) . . . . ?
C21 C22 C27 C28 42.2(3) . . . . ?
C23 C22 C27 C28 177.6(2) . . . . ?
C26 C27 C28 C29 -153.9(2) . . . . ?
C22 C27 C28 C29 -31.8(3) . . . . ?
C27 C28 C29 C21 9.4(3) . . . . ?
O30 C21 C29 C28 137.5(2) . . . . ?
C22 C21 C29 C28 17.2(3) . . . . ?
C22 C23 C31 C32 1.0(4) . . . . ?
C24 C23 C31 C32 178.3(3) . . . . ?
C22 C23 C31 C33 -177.8(3) . . . . ?
C24 C23 C31 C33 -0.4(4) . . . . ?
O50 C41 C42 C43 78.2(3) . . . . ?
C49 C41 C42 C43 -160.3(3) . . . . ?
O50 C41 C42 C47 -154.6(2) . . . . ?
C49 C41 C42 C47 -33.1(3) . . . . ?
C41 C42 C43 C51 -2.8(5) . . . . ?
C47 C42 C43 C51 -126.8(3) . . . . ?
C41 C42 C43 C44 -179.1(2) . . . . ?
C47 C42 C43 C44 56.9(3) . . . . ?
C51 C43 C44 C45 154.9(3) . . . . ?
C42 C43 C44 C45 -28.4(3) . . . . ?
C43 C44 C45 C46 -2.7(4) . . . . ?
C44 C45 C46 C47 4.7(4) . . . . ?
C45 C46 C47 C48 140.6(3) . . . . ?
C45 C46 C47 C42 24.5(4) . . . . ?
C41 C42 C47 C46 168.8(2) . . . . ?
C43 C42 C47 C46 -55.5(3) . . . . ?
C41 C42 C47 C48 43.8(3) . . . . ?
C43 C42 C47 C48 179.5(2) . . . . ?
C46 C47 C48 C49 -158.7(3) . . . . ?
C42 C47 C48 C49 -37.6(3) . . . . ?
C47 C48 C49 C41 17.3(3) . . . . ?
O50 C41 C49 C48 128.4(3) . . . . ?
C42 C41 C49 C48 9.8(3) . . . . ?
C44 C43 C51 C52 176.6(3) . . . . ?
C42 C43 C51 C52 0.6(5) . . . . ?
C44 C43 C51 C53 -2.5(4) . . . . ?
C42 C43 C51 C53 -178.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O10 H10 O30 0.90 1.76 2.661(3) 177.5 .
O30 H30 O50 0.94 1.73 2.664(3) 176.1 .
O50 H50 O10 1.01 1.66 2.673(3) 175.1 1_455

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_18MCD005B
_database_code_depnum_ccdc_archive 'CCDC 1964186'
loop_
_audit_author_name
_audit_author_address
'Lopez F'
;CSIC and USC
Spain
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'RN5 - 347 - 18MCD005'
_chemical_formula_moiety         'C19 H24 N2 O6'
_chemical_formula_sum            'C19 H24 N2 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         376.40

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.540(3)
_cell_length_b                   8.3364(13)
_cell_length_c                   11.3992(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.016(9)
_cell_angle_gamma                90
_cell_volume                     1849.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1626
_cell_measurement_theta_min      2.6579
_cell_measurement_theta_max      23.3230
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800

_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'SIEMENS KFN MO 2K-90'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker AXS X8 APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14731
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_av_unetI/netI     0.1058
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3771
_reflns_number_gt                1982
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1486
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_refine_ls_number_reflns         3771
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.303
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.26827(14) 0.3658(4) 0.5050(2) 0.0230(7) Uani d . . . 1 . .
H H1 0.297538 0.333651 0.577503 0.028 Uiso calc U . R 1 . .
C C2 0.22666(14) 0.5122(4) 0.5299(2) 0.0222(7) Uani d . . . 1 . .
H H2A 0.199985 0.547314 0.45656 0.027 Uiso calc U . R 1 . .
H H2B 0.257956 0.600575 0.557134 0.027 Uiso calc U . R 1 . .
C C3 0.17760(14) 0.4766(4) 0.6238(2) 0.0244(7) Uani d . . . 1 . .
H H3 0.206716 0.435124 0.693807 0.029 Uiso calc U . R 1 . .
C C4 0.14072(15) 0.6274(4) 0.6664(2) 0.0279(7) Uani d . . . 1 . .
C C5 0.09035(17) 0.5748(4) 0.7552(3) 0.0443(10) Uani d . . . 1 . .
H H5A 0.116864 0.531443 0.826175 0.053 Uiso calc U . R 1 . .
H H5B 0.064843 0.670057 0.779574 0.053 Uiso calc U . R 1 . .
C C6 0.03899(19) 0.4486(5) 0.7071(3) 0.0530(11) Uani d . . . 1 . .
H H6A 0.010225 0.492753 0.638855 0.064 Uiso calc U . R 1 . .
H H6B 0.008427 0.418977 0.768473 0.064 Uiso calc U . R 1 . .
C C7 0.07744(17) 0.2985(4) 0.6688(3) 0.0436(9) Uani d . . . 1 . .
H H7A 0.101146 0.246655 0.739202 0.052 Uiso calc U . R 1 . .
H H7B 0.043838 0.220926 0.631619 0.052 Uiso calc U . R 1 . .
C C8 0.12971(15) 0.3398(4) 0.5827(3) 0.0322(8) Uani d . . . 1 . .
H H8 0.103372 0.375981 0.508214 0.039 Uiso calc U . R 1 . .
C C9 0.17115(16) 0.1919(4) 0.5520(3) 0.0351(8) Uani d . . . 1 . .
H H9A 0.196139 0.149758 0.624824 0.042 Uiso calc U . R 1 . .
H H9B 0.139076 0.107439 0.520139 0.042 Uiso calc U . R 1 . .
C C10 0.22262(15) 0.2274(4) 0.4623(3) 0.0323(8) Uani d . . . 1 . .
H H10A 0.251035 0.131156 0.451252 0.039 Uiso calc U . R 1 . .
H H10B 0.197802 0.254908 0.38544 0.039 Uiso calc U . R 1 . .
C C11 0.10216(17) 0.7175(4) 0.5630(3) 0.0439(9) Uani d . . . 1 . .
H H11A 0.135098 0.755306 0.509052 0.066 Uiso calc U . R 1 . .
H H11B 0.077808 0.809405 0.593063 0.066 Uiso calc U . R 1 . .
H H11C 0.06902 0.644995 0.52084 0.066 Uiso calc U . R 1 . .
C C12 0.19211(17) 0.7438(4) 0.7285(3) 0.0452(10) Uani d . . . 1 . .
H H12A 0.223408 0.783257 0.672329 0.068 Uiso calc U . R 1 . .
H H12B 0.21855 0.688531 0.793427 0.068 Uiso calc U . R 1 . .
H H12C 0.167393 0.834502 0.759622 0.068 Uiso calc U . R 1 . .
O O13 0.31185(9) 0.4093(2) 0.41163(16) 0.0243(5) Uani d . . . 1 . .
C C14 0.37904(14) 0.3825(3) 0.4284(2) 0.0196(6) Uani d . . . 1 . .
O O15 0.40836(9) 0.3176(2) 0.51281(16) 0.0230(5) Uani d . . . 1 . .
C C16 0.41523(14) 0.4446(3) 0.3274(2) 0.0174(6) Uani d . . . 1 . .
C C17 0.38041(14) 0.5046(3) 0.2253(2) 0.0199(6) Uani d . . . 1 . .
H H17 0.331619 0.505383 0.216217 0.024 Uiso calc U . R 1 . .
C C18 0.41768(14) 0.5632(3) 0.1372(2) 0.0190(6) Uani d . . . 1 . .
C C19 0.48857(14) 0.5650(3) 0.1459(2) 0.0185(6) Uani d . . . 1 . .
H H19 0.513415 0.607973 0.085153 0.022 Uiso calc U . R 1 . .
C C20 0.52145(13) 0.5013(3) 0.2471(2) 0.0170(6) Uani d . . . 1 . .
C C21 0.48658(14) 0.4419(3) 0.3382(2) 0.0194(7) Uani d . . . 1 . .
H H21 0.511038 0.399863 0.407123 0.023 Uiso calc U . R 1 . .
N N22 0.38063(12) 0.6290(3) 0.03016(19) 0.0200(5) Uani d . . . 1 . .
O O23 0.31818(10) 0.6138(2) 0.01734(16) 0.0269(5) Uani d . . . 1 . .
O O24 0.41528(9) 0.6977(2) -0.04122(16) 0.0241(5) Uani d . . . 1 . .
N N25 0.59726(11) 0.4966(3) 0.2593(2) 0.0203(5) Uani d . . . 1 . .
O O26 0.62528(9) 0.4009(2) 0.33027(16) 0.0226(5) Uani d . . . 1 . .
O O27 0.62860(9) 0.5882(2) 0.19845(16) 0.0237(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O13 . 1.465(3) ?
C1 C2 . 1.507(4) ?
C1 C10 . 1.513(4) ?
C1 H1 . 1.0 ?
C2 C3 . 1.527(4) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C8 . 1.523(4) ?
C3 C4 . 1.549(4) ?
C3 H3 . 1.0 ?
C4 C12 . 1.525(4) ?
C4 C5 . 1.536(4) ?
C4 C11 . 1.538(4) ?
C5 C6 . 1.523(5) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.542(5) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.517(4) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.532(4) ?
C8 H8 . 1.0 ?
C9 C10 . 1.525(4) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
O13 C14 . 1.329(3) ?
C14 O15 . 1.205(3) ?
C14 C16 . 1.495(4) ?
C16 C17 . 1.389(4) ?
C16 C21 . 1.389(4) ?
C17 C18 . 1.380(4) ?
C17 H17 . 0.95 ?
C18 C19 . 1.380(4) ?
C18 N22 . 1.470(3) ?
C19 C20 . 1.377(4) ?
C19 H19 . 0.95 ?
C20 C21 . 1.383(4) ?
C20 N25 . 1.476(3) ?
C21 H21 . 0.95 ?
N22 O23 . 1.223(3) ?
N22 O24 . 1.243(3) ?
N25 O26 . 1.230(3) ?
N25 O27 . 1.230(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O13 C1 C2 . . 107.1(2) ?
O13 C1 C10 . . 108.6(2) ?
C2 C1 C10 . . 111.4(2) ?
O13 C1 H1 . . 109.9 ?
C2 C1 H1 . . 109.9 ?
C10 C1 H1 . . 109.9 ?
C1 C2 C3 . . 110.9(2) ?
C1 C2 H2A . . 109.5 ?
C3 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 108.0 ?
C8 C3 C2 . . 109.6(2) ?
C8 C3 C4 . . 114.5(2) ?
C2 C3 C4 . . 113.6(2) ?
C8 C3 H3 . . 106.2 ?
C2 C3 H3 . . 106.2 ?
C4 C3 H3 . . 106.2 ?
C12 C4 C5 . . 108.0(3) ?
C12 C4 C11 . . 107.7(3) ?
C5 C4 C11 . . 110.2(3) ?
C12 C4 C3 . . 110.9(2) ?
C5 C4 C3 . . 108.5(3) ?
C11 C4 C3 . . 111.5(2) ?
C6 C5 C4 . . 113.6(3) ?
C6 C5 H5A . . 108.9 ?
C4 C5 H5A . . 108.9 ?
C6 C5 H5B . . 108.9 ?
C4 C5 H5B . . 108.9 ?
H5A C5 H5B . . 107.7 ?
C5 C6 C7 . . 109.9(3) ?
C5 C6 H6A . . 109.7 ?
C7 C6 H6A . . 109.7 ?
C5 C6 H6B . . 109.7 ?
C7 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
C8 C7 C6 . . 111.8(3) ?
C8 C7 H7A . . 109.3 ?
C6 C7 H7A . . 109.3 ?
C8 C7 H7B . . 109.3 ?
C6 C7 H7B . . 109.3 ?
H7A C7 H7B . . 107.9 ?
C7 C8 C3 . . 113.6(3) ?
C7 C8 C9 . . 111.4(3) ?
C3 C8 C9 . . 110.5(2) ?
C7 C8 H8 . . 107.0 ?
C3 C8 H8 . . 107.0 ?
C9 C8 H8 . . 107.0 ?
C10 C9 C8 . . 112.9(3) ?
C10 C9 H9A . . 109.0 ?
C8 C9 H9A . . 109.0 ?
C10 C9 H9B . . 109.0 ?
C8 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
C1 C10 C9 . . 109.7(2) ?
C1 C10 H10A . . 109.7 ?
C9 C10 H10A . . 109.7 ?
C1 C10 H10B . . 109.7 ?
C9 C10 H10B . . 109.7 ?
H10A C10 H10B . . 108.2 ?
C4 C11 H11A . . 109.5 ?
C4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C4 C12 H12A . . 109.5 ?
C4 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C4 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 O13 C1 . . 118.9(2) ?
O15 C14 O13 . . 125.8(2) ?
O15 C14 C16 . . 123.2(2) ?
O13 C14 C16 . . 111.0(2) ?
C17 C16 C21 . . 119.6(2) ?
C17 C16 C14 . . 122.7(2) ?
C21 C16 C14 . . 117.7(2) ?
C18 C17 C16 . . 119.1(3) ?
C18 C17 H17 . . 120.5 ?
C16 C17 H17 . . 120.5 ?
C17 C18 C19 . . 122.8(3) ?
C17 C18 N22 . . 118.9(2) ?
C19 C18 N22 . . 118.3(2) ?
C20 C19 C18 . . 116.6(2) ?
C20 C19 H19 . . 121.7 ?
C18 C19 H19 . . 121.7 ?
C19 C20 C21 . . 122.9(3) ?
C19 C20 N25 . . 118.7(2) ?
C21 C20 N25 . . 118.4(2) ?
C20 C21 C16 . . 119.0(3) ?
C20 C21 H21 . . 120.5 ?
C16 C21 H21 . . 120.5 ?
O23 N22 O24 . . 124.4(2) ?
O23 N22 C18 . . 118.3(2) ?
O24 N22 C18 . . 117.3(2) ?
O26 N25 O27 . . 124.0(2) ?
O26 N25 C20 . . 117.7(2) ?
O27 N25 C20 . . 118.4(2) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O13 C1 C2 C3 . . . . 178.1(2) ?
C10 C1 C2 C3 . . . . 59.5(3) ?
C1 C2 C3 C8 . . . . -58.7(3) ?
C1 C2 C3 C4 . . . . 171.8(2) ?
C8 C3 C4 C12 . . . . 168.6(3) ?
C2 C3 C4 C12 . . . . -64.5(3) ?
C8 C3 C4 C5 . . . . 50.1(3) ?
C2 C3 C4 C5 . . . . 177.0(3) ?
C8 C3 C4 C11 . . . . -71.5(3) ?
C2 C3 C4 C11 . . . . 55.5(3) ?
C12 C4 C5 C6 . . . . -175.9(3) ?
C11 C4 C5 C6 . . . . 66.7(4) ?
C3 C4 C5 C6 . . . . -55.6(4) ?
C4 C5 C6 C7 . . . . 58.7(4) ?
C5 C6 C7 C8 . . . . -54.3(4) ?
C6 C7 C8 C3 . . . . 50.4(4) ?
C6 C7 C8 C9 . . . . 176.0(3) ?
C2 C3 C8 C7 . . . . -178.3(3) ?
C4 C3 C8 C7 . . . . -49.4(4) ?
C2 C3 C8 C9 . . . . 55.6(3) ?
C4 C3 C8 C9 . . . . -175.4(2) ?
C7 C8 C9 C10 . . . . 178.0(3) ?
C3 C8 C9 C10 . . . . -54.7(4) ?
O13 C1 C10 C9 . . . . -173.7(2) ?
C2 C1 C10 C9 . . . . -55.9(3) ?
C8 C9 C10 C1 . . . . 54.0(4) ?
C2 C1 O13 C14 . . . . 127.5(2) ?
C10 C1 O13 C14 . . . . -112.0(3) ?
C1 O13 C14 O15 . . . . 3.7(4) ?
C1 O13 C14 C16 . . . . -176.2(2) ?
O15 C14 C16 C17 . . . . 173.3(3) ?
O13 C14 C16 C17 . . . . -6.8(4) ?
O15 C14 C16 C21 . . . . -7.0(4) ?
O13 C14 C16 C21 . . . . 172.8(2) ?
C21 C16 C17 C18 . . . . -1.2(4) ?
C14 C16 C17 C18 . . . . 178.5(3) ?
C16 C17 C18 C19 . . . . 0.0(4) ?
C16 C17 C18 N22 . . . . -179.0(2) ?
C17 C18 C19 C20 . . . . 1.5(4) ?
N22 C18 C19 C20 . . . . -179.5(2) ?
C18 C19 C20 C21 . . . . -1.8(4) ?
C18 C19 C20 N25 . . . . 178.5(2) ?
C19 C20 C21 C16 . . . . 0.7(4) ?
N25 C20 C21 C16 . . . . -179.6(2) ?
C17 C16 C21 C20 . . . . 0.8(4) ?
C14 C16 C21 C20 . . . . -178.8(2) ?
C17 C18 N22 O23 . . . . -7.8(4) ?
C19 C18 N22 O23 . . . . 173.2(2) ?
C17 C18 N22 O24 . . . . 171.7(2) ?
C19 C18 N22 O24 . . . . -7.3(4) ?
C19 C20 N25 O26 . . . . -159.2(2) ?
C21 C20 N25 O26 . . . . 21.0(3) ?
C19 C20 N25 O27 . . . . 20.9(4) ?
C21 C20 N25 O27 . . . . -158.9(2) ?

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1964188'
loop_
_audit_author_name
_audit_author_address
'Fernando Lopez'
;CSIC and USC
Spain
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;

_audit_creation_date             2016-11-19T21:12:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        ' '
_chemical_name_common            RN1-601
_chemical_formula_moiety         'C19 H34 O Si'
_chemical_formula_sum            'C19 H34 O Si'
_chemical_formula_weight         306.55

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.4244(10)
_cell_length_b                   6.2336(3)
_cell_length_c                   13.0105(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.557(2)
_cell_angle_gamma                90
_cell_volume                     1899.68(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8169
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      31.38
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.962
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.988

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.029575
_diffrn_orient_matrix_ub_12      0.038676
_diffrn_orient_matrix_ub_13      -0.051725
_diffrn_orient_matrix_ub_21      0.002167
_diffrn_orient_matrix_ub_22      -0.153431
_diffrn_orient_matrix_ub_23      -0.022061
_diffrn_orient_matrix_ub_31      -0.030713
_diffrn_orient_matrix_ub_32      0.026417
_diffrn_orient_matrix_ub_33      -0.052403
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_number            40894
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.739
_diffrn_reflns_theta_max         33.244
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_reflns_Friedel_coverage         0
_reflns_number_total             7142
_reflns_number_gt                5087
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.37A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0569P)²+0.4038P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7142
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.049
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.41
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Si1 Si 0.15566(2) 0.41357(5) 0.29204(2) 0.01304(8) Uani 1 1 d . . . . .
O1 O 0.20044(3) 0.31511(14) 0.37857(6) 0.01681(17) Uani 1 1 d . . . . .
C1 C 0.25118(5) 0.19498(19) 0.35707(9) 0.0158(2) Uani 1 1 d . . . . .
H1 H 0.24846 0.120992 0.288995 0.019 Uiso 1 1 calc R U . . .
C2 C 0.30233(5) 0.34299(19) 0.36271(8) 0.0145(2) Uani 1 1 d . . . . .
H2 H 0.30012 0.4859 0.327986 0.017 Uiso 1 1 calc R U . . .
C3 C 0.32679(5) 0.33022(18) 0.47224(8) 0.0134(2) Uani 1 1 d . . . . .
C4 C 0.29103(5) 0.1654(2) 0.52947(9) 0.0178(2) Uani 1 1 d . . . . .
H4A H 0.262945 0.237177 0.574243 0.021 Uiso 1 1 calc R U . . .
H4B H 0.315651 0.07146 0.572342 0.021 Uiso 1 1 calc R U . . .
C5 C 0.26058(5) 0.0349(2) 0.44490(10) 0.0190(2) Uani 1 1 d . . . . .
H5A H 0.28461 -0.086686 0.422349 0.023 Uiso 1 1 calc R U . . .
H5B H 0.223709 -0.021789 0.469668 0.023 Uiso 1 1 calc R U . . .
C6 C 0.36017(5) 0.24352(19) 0.38191(8) 0.0144(2) Uani 1 1 d . . . . .
H6 H 0.361043 0.083487 0.376796 0.017 Uiso 1 1 calc R U . . .
C7 C 0.41582(5) 0.3542(2) 0.35384(9) 0.0159(2) Uani 1 1 d . . . . .
C8 C 0.41299(5) 0.5967(2) 0.37599(9) 0.0181(2) Uani 1 1 d . . . . .
H8A H 0.451972 0.657341 0.372117 0.022 Uiso 1 1 calc R U . . .
H8B H 0.3894 0.666559 0.322059 0.022 Uiso 1 1 calc R U . . .
C9 C 0.38842(5) 0.6487(2) 0.47961(9) 0.0173(2) Uani 1 1 d . . . . .
H9 H 0.401518 0.773276 0.514663 0.021 Uiso 1 1 calc R U . . .
C10 C 0.34894(5) 0.52642(19) 0.52404(9) 0.0150(2) Uani 1 1 d . . . . .
C11 C 0.42866(6) 0.3198(2) 0.23959(10) 0.0237(3) Uani 1 1 d . . . . .
H11A H 0.397626 0.380465 0.197717 0.036 Uiso 1 1 calc R U . . .
H11B H 0.431929 0.165857 0.22558 0.036 Uiso 1 1 calc R U . . .
H11C H 0.464618 0.391163 0.222496 0.036 Uiso 1 1 calc R U . . .
C12 C 0.46336(5) 0.2524(2) 0.41961(10) 0.0213(2) Uani 1 1 d . . . . .
H12A H 0.464406 0.097477 0.407024 0.032 Uiso 1 1 calc R U . . .
H12B H 0.455855 0.279013 0.492477 0.032 Uiso 1 1 calc R U . . .
H12C H 0.500178 0.315802 0.40132 0.032 Uiso 1 1 calc R U . . .
C13 C 0.32336(6) 0.5860(2) 0.62605(9) 0.0217(3) Uani 1 1 d . . . . .
H13A H 0.282388 0.61265 0.617021 0.033 Uiso 1 1 calc R U . . .
H13B H 0.341953 0.715849 0.652489 0.033 Uiso 1 1 calc R U . . .
H13C H 0.329119 0.468171 0.674934 0.033 Uiso 1 1 calc R U . . .
C14 C 0.18983(6) 0.6382(2) 0.22111(10) 0.0233(3) Uani 1 1 d . . . . .
H14A H 0.223877 0.585263 0.186017 0.035 Uiso 1 1 calc R U . . .
H14B H 0.200805 0.75142 0.269678 0.035 Uiso 1 1 calc R U . . .
H14C H 0.162793 0.696127 0.170297 0.035 Uiso 1 1 calc R U . . .
C15 C 0.13424(6) 0.2041(2) 0.19724(10) 0.0232(3) Uani 1 1 d . . . . .
H15A H 0.103938 0.260367 0.152311 0.035 Uiso 1 1 calc R U . . .
H15B H 0.120224 0.077437 0.233765 0.035 Uiso 1 1 calc R U . . .
H15C H 0.167286 0.16433 0.155736 0.035 Uiso 1 1 calc R U . . .
C16 C 0.09250(5) 0.5052(2) 0.36910(9) 0.0164(2) Uani 1 1 d . . . . .
C17 C 0.04775(6) 0.6123(2) 0.29905(11) 0.0251(3) Uani 1 1 d . . . . .
H17A H 0.064724 0.737318 0.265399 0.038 Uiso 1 1 calc R U . . .
H17B H 0.015166 0.658345 0.34028 0.038 Uiso 1 1 calc R U . . .
H17C H 0.03478 0.509677 0.246766 0.038 Uiso 1 1 calc R U . . .
C18 C 0.11202(6) 0.6649(2) 0.45205(10) 0.0244(3) Uani 1 1 d . . . . .
H18A H 0.126432 0.795338 0.419234 0.037 Uiso 1 1 calc R U . . .
H18B H 0.142433 0.59997 0.493933 0.037 Uiso 1 1 calc R U . . .
H18C H 0.079679 0.701278 0.495966 0.037 Uiso 1 1 calc R U . . .
C19 C 0.06537(6) 0.3075(2) 0.42082(10) 0.0231(3) Uani 1 1 d . . . . .
H19A H 0.05018 0.210691 0.367887 0.035 Uiso 1 1 calc R U . . .
H19B H 0.034316 0.354092 0.465555 0.035 Uiso 1 1 calc R U . . .
H19C H 0.094394 0.232244 0.461864 0.035 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Si1 O1 1.6497(9) . ?
Si1 C15 1.8616(13) . ?
Si1 C14 1.8620(13) . ?
Si1 C16 1.8841(12) . ?
O1 C1 1.4346(14) . ?
C1 C2 1.5135(16) . ?
C1 C5 1.5315(17) . ?
C1 H1 1 . ?
C2 C6 1.5085(16) . ?
C2 C3 1.5327(15) . ?
C2 H2 1 . ?
C3 C10 1.4874(16) . ?
C3 C6 1.5174(15) . ?
C3 C4 1.5245(16) . ?
C4 C5 1.5381(17) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.5226(16) . ?
C6 H6 1 . ?
C7 C11 1.5345(17) . ?
C7 C12 1.5350(17) . ?
C7 C8 1.5402(17) . ?
C8 C9 1.5064(17) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.3343(17) . ?
C9 H9 0.95 . ?
C10 C13 1.5079(16) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 C18 1.5347(17) . ?
C16 C17 1.5351(18) . ?
C16 C19 1.5440(17) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Si1 C15 110.90(6) . . ?
O1 Si1 C14 110.15(6) . . ?
C15 Si1 C14 108.27(6) . . ?
O1 Si1 C16 104.30(5) . . ?
C15 Si1 C16 110.93(6) . . ?
C14 Si1 C16 112.29(6) . . ?
C1 O1 Si1 125.70(7) . . ?
O1 C1 C2 109.23(9) . . ?
O1 C1 C5 107.94(9) . . ?
C2 C1 C5 104.65(9) . . ?
O1 C1 H1 111.6 . . ?
C2 C1 H1 111.6 . . ?
C5 C1 H1 111.6 . . ?
C6 C2 C1 117.83(10) . . ?
C6 C2 C3 59.85(7) . . ?
C1 C2 C3 107.58(9) . . ?
C6 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C10 C3 C6 117.62(10) . . ?
C10 C3 C4 121.60(10) . . ?
C6 C3 C4 115.33(10) . . ?
C10 C3 C2 120.27(10) . . ?
C6 C3 C2 59.28(7) . . ?
C4 C3 C2 106.67(9) . . ?
C3 C4 C5 105.09(9) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C1 C5 C4 104.56(10) . . ?
C1 C5 H5A 110.8 . . ?
C4 C5 H5A 110.8 . . ?
C1 C5 H5B 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C2 C6 C3 60.87(7) . . ?
C2 C6 C7 122.93(10) . . ?
C3 C6 C7 118.25(10) . . ?
C2 C6 H6 114.7 . . ?
C3 C6 H6 114.7 . . ?
C7 C6 H6 114.7 . . ?
C6 C7 C11 110.20(10) . . ?
C6 C7 C12 107.29(10) . . ?
C11 C7 C12 109.53(10) . . ?
C6 C7 C8 111.18(10) . . ?
C11 C7 C8 109.12(10) . . ?
C12 C7 C8 109.49(10) . . ?
C9 C8 C7 113.34(10) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 122.49(11) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C3 120.91(10) . . ?
C9 C10 C13 121.57(11) . . ?
C3 C10 C13 117.48(10) . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C16 C17 109.42(11) . . ?
C18 C16 C19 109.40(10) . . ?
C17 C16 C19 108.93(10) . . ?
C18 C16 Si1 109.91(8) . . ?
C17 C16 Si1 110.56(8) . . ?
C19 C16 Si1 108.58(8) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
C15 Si1 O1 C1 50.27(11) . . . . ?
C14 Si1 O1 C1 -69.57(10) . . . . ?
C16 Si1 O1 C1 169.73(9) . . . . ?
Si1 O1 C1 C2 98.39(10) . . . . ?
Si1 O1 C1 C5 -148.37(8) . . . . ?
O1 C1 C2 C6 157.76(9) . . . . ?
C5 C1 C2 C6 42.39(13) . . . . ?
O1 C1 C2 C3 93.13(11) . . . . ?
C5 C1 C2 C3 -22.24(12) . . . . ?
C6 C2 C3 C10 106.12(11) . . . . ?
C1 C2 C3 C10 -141.41(10) . . . . ?
C1 C2 C3 C6 112.47(10) . . . . ?
C6 C2 C3 C4 -109.97(10) . . . . ?
C1 C2 C3 C4 2.50(12) . . . . ?
C10 C3 C4 C5 161.50(10) . . . . ?
C6 C3 C4 C5 -45.20(13) . . . . ?
C2 C3 C4 C5 18.17(12) . . . . ?
O1 C1 C5 C4 -82.90(11) . . . . ?
C2 C1 C5 C4 33.36(12) . . . . ?
C3 C4 C5 C1 -31.90(12) . . . . ?
C1 C2 C6 C3 -95.07(11) . . . . ?
C1 C2 C6 C7 158.40(10) . . . . ?
C3 C2 C6 C7 -106.53(12) . . . . ?
C10 C3 C6 C2 -110.54(11) . . . . ?
C4 C3 C6 C2 95.05(11) . . . . ?
C10 C3 C6 C7 3.48(15) . . . . ?
C4 C3 C6 C7 -150.93(10) . . . . ?
C2 C3 C6 C7 114.02(12) . . . . ?
C2 C6 C7 C11 -82.22(14) . . . . ?
C3 C6 C7 C11 -154.13(10) . . . . ?
C2 C6 C7 C12 158.60(10) . . . . ?
C3 C6 C7 C12 86.68(12) . . . . ?
C2 C6 C7 C8 38.91(14) . . . . ?
C3 C6 C7 C8 -33.00(14) . . . . ?
C6 C7 C8 C9 45.89(14) . . . . ?
C11 C7 C8 C9 167.65(10) . . . . ?
C12 C7 C8 C9 -72.48(13) . . . . ?
C7 C8 C9 C10 -31.39(17) . . . . ?
C8 C9 C10 C3 -0.28(18) . . . . ?
C8 C9 C10 C13 -177.71(11) . . . . ?
C6 C3 C10 C9 14.91(16) . . . . ?
C4 C3 C10 C9 167.63(11) . . . . ?
C2 C3 C10 C9 -53.86(16) . . . . ?
C6 C3 C10 C13 -167.56(10) . . . . ?
C4 C3 C10 C13 -14.84(16) . . . . ?
C2 C3 C10 C13 123.67(12) . . . . ?
O1 Si1 C16 C18 56.26(10) . . . . ?
C15 Si1 C16 C18 175.71(9) . . . . ?
C14 Si1 C16 C18 -63.00(10) . . . . ?
O1 Si1 C16 C17 177.17(8) . . . . ?
C15 Si1 C16 C17 -63.38(10) . . . . ?
C14 Si1 C16 C17 57.91(10) . . . . ?
O1 Si1 C16 C19 -63.38(9) . . . . ?
C15 Si1 C16 C19 56.07(10) . . . . ?
C14 Si1 C16 C19 177.36(9) . . . . ?

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1964187'
loop_
_audit_author_name
_audit_author_address
'Lopez F'
;CSIC and USC
Spain
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;

_audit_creation_date             2017-03-08T12:31:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        ' '
_chemical_name_common            LM1RN5-137
_chemical_formula_moiety         'C12 H18 O'
_chemical_formula_sum            'C12 H18 O'
_chemical_formula_weight         178.26

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
_space_group_IT_number           88
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   22.3413(4)
_cell_length_b                   22.3413(4)
_cell_length_c                   8.6532(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4319.10(18)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9829
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      30.51
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.96
_shelx_estimated_absorpt_T_min   0.96
_shelx_estimated_absorpt_T_max   0.993

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.015962
_diffrn_orient_matrix_ub_12      -0.040804
_diffrn_orient_matrix_ub_13      -0.023627
_diffrn_orient_matrix_ub_21      -0.03936
_diffrn_orient_matrix_ub_22      0.017968
_diffrn_orient_matrix_ub_23      -0.029595
_diffrn_orient_matrix_ub_31      0.014123
_diffrn_orient_matrix_ub_32      0.00396
_diffrn_orient_matrix_ub_33      -0.109183
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_number            77039
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.823
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3313
_reflns_number_gt                2711
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.37A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+2.1920P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3313
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.28859(3) 0.46827(4) 0.44460(9) 0.0352(2) Uani 1 1 d . . . . .
H1 H 0.2836(7) 0.4918(7) 0.525(2) 0.053 Uiso 1 1 d . U . . .
C1 C 0.34825(4) 0.44443(5) 0.45317(11) 0.0313(2) Uani 1 1 d . . . . .
H1C H 0.375536 0.476205 0.493941 0.038 Uiso 1 1 calc R U . . .
C2 C 0.36756(4) 0.42850(4) 0.29218(10) 0.0257(2) Uani 1 1 d . . . . .
H2 H 0.375299 0.460477 0.222618 0.031 Uiso 1 1 calc R U . . .
C3 C 0.37463(4) 0.37309(4) 0.23960(9) 0.02075(18) Uani 1 1 d . . . . .
C4 C 0.39548(4) 0.35900(4) 0.07602(10) 0.02376(19) Uani 1 1 d . . . . .
C5 C 0.34548(4) 0.32292(5) -0.00374(12) 0.0312(2) Uani 1 1 d . . . . .
H5A H 0.312648 0.350451 -0.0329 0.037 Uiso 1 1 calc R U . . .
H5B H 0.361497 0.304939 -0.099779 0.037 Uiso 1 1 calc R U . . .
C6 C 0.32086(6) 0.27436(5) 0.09664(17) 0.0441(3) Uani 1 1 d . . . . .
H6 H 0.298251 0.243403 0.049153 0.053 Uiso 1 1 calc R U . . .
C7 C 0.32880(6) 0.27217(5) 0.24736(17) 0.0438(3) Uani 1 1 d . . . . .
H7 H 0.313226 0.23859 0.301406 0.053 Uiso 1 1 calc R U . . .
C8 C 0.36088(5) 0.31929(5) 0.33932(12) 0.0305(2) Uani 1 1 d . . . . .
H8 H 0.399736 0.302011 0.375395 0.037 Uiso 1 1 calc R U . . .
C9 C 0.32414(5) 0.33651(5) 0.48250(12) 0.0344(2) Uani 1 1 d . . . . .
H9A H 0.282355 0.345069 0.451481 0.041 Uiso 1 1 calc R U . . .
H9B H 0.323572 0.302568 0.556045 0.041 Uiso 1 1 calc R U . . .
C10 C 0.35061(5) 0.39108(6) 0.56082(11) 0.0386(3) Uani 1 1 d . . . . .
H10A H 0.327872 0.400063 0.656244 0.046 Uiso 1 1 calc R U . . .
H10B H 0.392662 0.382891 0.590043 0.046 Uiso 1 1 calc R U . . .
C11 C 0.40881(5) 0.41461(5) -0.01966(12) 0.0361(3) Uani 1 1 d . . . . .
H11A H 0.420785 0.40268 -0.124172 0.054 Uiso 1 1 calc R U . . .
H11B H 0.441343 0.437254 0.028856 0.054 Uiso 1 1 calc R U . . .
H11C H 0.372892 0.439693 -0.025272 0.054 Uiso 1 1 calc R U . . .
C12 C 0.45260(5) 0.32035(6) 0.08305(13) 0.0362(2) Uani 1 1 d . . . . .
H12A H 0.466324 0.311649 -0.022148 0.054 Uiso 1 1 calc R U . . .
H12B H 0.443841 0.282756 0.136813 0.054 Uiso 1 1 calc R U . . .
H12C H 0.483952 0.342098 0.138947 0.054 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4372(12) . ?
O1 H1 0.878(18) . ?
C1 C2 1.5011(13) . ?
C1 C10 1.5137(17) . ?
C1 H1C 1 . ?
C2 C3 1.3283(13) . ?
C2 H2 0.95 . ?
C3 C8 1.5112(12) . ?
C3 C4 1.5230(12) . ?
C4 C11 1.5224(14) . ?
C4 C5 1.5407(13) . ?
C4 C12 1.5421(14) . ?
C5 C6 1.4946(17) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.317(2) . ?
C6 H6 0.95 . ?
C7 C8 1.5018(17) . ?
C7 H7 0.95 . ?
C8 C9 1.5352(14) . ?
C8 H8 1 . ?
C9 C10 1.5152(18) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?

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 O1 H1 107.4(10) . . ?
O1 C1 C2 107.85(8) . . ?
O1 C1 C10 110.85(9) . . ?
C2 C1 C10 111.99(9) . . ?
O1 C1 H1C 108.7 . . ?
C2 C1 H1C 108.7 . . ?
C10 C1 H1C 108.7 . . ?
C3 C2 C1 124.96(9) . . ?
C3 C2 H2 117.5 . . ?
C1 C2 H2 117.5 . . ?
C2 C3 C8 121.43(8) . . ?
C2 C3 C4 123.18(8) . . ?
C8 C3 C4 115.37(8) . . ?
C11 C4 C3 113.37(8) . . ?
C11 C4 C5 108.98(8) . . ?
C3 C4 C5 107.62(7) . . ?
C11 C4 C12 108.45(8) . . ?
C3 C4 C12 109.40(8) . . ?
C5 C4 C12 108.95(8) . . ?
C6 C5 C4 112.72(9) . . ?
C6 C5 H5A 109 . . ?
C4 C5 H5A 109 . . ?
C6 C5 H5B 109 . . ?
C4 C5 H5B 109 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 123.57(10) . . ?
C7 C6 H6 118.2 . . ?
C5 C6 H6 118.2 . . ?
C6 C7 C8 124.25(10) . . ?
C6 C7 H7 117.9 . . ?
C8 C7 H7 117.9 . . ?
C7 C8 C3 110.62(9) . . ?
C7 C8 C9 110.37(9) . . ?
C3 C8 C9 111.73(8) . . ?
C7 C8 H8 108 . . ?
C3 C8 H8 108 . . ?
C9 C8 H8 108 . . ?
C10 C9 C8 110.72(9) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C1 C10 C9 110.17(8) . . ?
C1 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C1 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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 C1 C2 C3 -109.66(11) . . . . ?
C10 C1 C2 C3 12.56(14) . . . . ?
C1 C2 C3 C8 2.63(15) . . . . ?
C1 C2 C3 C4 -178.79(8) . . . . ?
C2 C3 C4 C11 1.40(13) . . . . ?
C8 C3 C4 C11 -179.94(8) . . . . ?
C2 C3 C4 C5 -119.19(10) . . . . ?
C8 C3 C4 C5 59.47(10) . . . . ?
C2 C3 C4 C12 122.58(10) . . . . ?
C8 C3 C4 C12 -58.76(10) . . . . ?
C11 C4 C5 C6 -168.51(9) . . . . ?
C3 C4 C5 C6 -45.19(11) . . . . ?
C12 C4 C5 C6 73.34(10) . . . . ?
C4 C5 C6 C7 16.92(16) . . . . ?
C5 C6 C7 C8 3.1(2) . . . . ?
C6 C7 C8 C3 8.16(16) . . . . ?
C6 C7 C8 C9 132.34(12) . . . . ?
C2 C3 C8 C7 138.10(10) . . . . ?
C4 C3 C8 C7 -40.59(11) . . . . ?
C2 C3 C8 C9 14.71(13) . . . . ?
C4 C3 C8 C9 -163.97(8) . . . . ?
C7 C8 C9 C10 -170.30(9) . . . . ?
C3 C8 C9 C10 -46.77(11) . . . . ?
O1 C1 C10 C9 76.18(10) . . . . ?
C2 C1 C10 C9 -44.31(11) . . . . ?
C8 C9 C10 C1 62.69(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.878(18) 1.804(18) 2.6780(6) 173.7(15) 3

####################################################################### 
# 
# 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_17MCD011
_database_code_depnum_ccdc_archive 'CCDC 1964185'
loop_
_audit_author_name
_audit_author_address
'Lopez F'
;CSIC and USC
Spain
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            RN5-163
_chemical_formula_moiety         'C20 H23 Br O2'
_chemical_formula_sum            'C20 H23 Br O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         375.29
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.4263(2)
_cell_length_b                   19.6250(3)
_cell_length_c                   15.7208(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3525.25(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7715
_cell_measurement_theta_min      2.5910
_cell_measurement_theta_max      28.6053
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.313
_exptl_crystal_size_min          0.295
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552

_exptl_absorpt_coefficient_mu    2.340
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_T_max  0.55

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'SIEMENS KFN MO 2K-90'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'κ--geometry diffractometer'
_diffrn_measurement_method       'φ or ω oscillation scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            35734
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_full        30.54
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             10744
_reflns_number_gt                7539
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0757
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.972
_refine_ls_number_reflns         10744
_refine_ls_number_parameters     421
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.432
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2892 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(5)

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.0055(3) 0.32168(19) 0.3773(2) 0.0279(9) Uani d . . . 1 . .
H H1 0.0075 0.2942 0.4309 0.033 Uiso calc U . R 1 . .
C C2 0.0031(3) 0.27444(18) 0.3022(2) 0.0211(8) Uani d . . . 1 . .
H H2 0.0577 0.2379 0.3009 0.025 Uiso calc U . R 1 . .
C C3 -0.0710(3) 0.28067(17) 0.2372(2) 0.0183(7) Uani d . . . 1 . .
C C4 -0.0778(3) 0.22968(18) 0.1640(2) 0.0181(7) Uani d . . . 1 . .
C C5 -0.0481(3) 0.26870(19) 0.0830(2) 0.0231(8) Uani d . . . 1 . .
H H5A 0.0368 0.2786 0.0824 0.028 Uiso calc U . R 1 . .
H H5B -0.0658 0.2396 0.0332 0.028 Uiso calc U . R 1 . .
C C6 -0.1144(3) 0.33431(19) 0.0748(2) 0.0262(9) Uani d . . . 1 . .
H H6 -0.1204 0.3545 0.02 0.031 Uiso calc U . R 1 . .
C C7 -0.1651(3) 0.36581(17) 0.1399(3) 0.0241(8) Uani d . . . 1 . .
C C8 -0.1561(3) 0.33974(17) 0.2299(2) 0.0229(8) Uani d . . . 1 . .
H H8 -0.2351 0.3224 0.2465 0.027 Uiso calc U . R 1 . .
C C9 -0.1245(3) 0.39722(19) 0.2917(2) 0.0270(8) Uani d . . . 1 . .
H H9A -0.0548 0.4219 0.2705 0.032 Uiso calc U . R 1 . .
H H9B -0.1901 0.43 0.2953 0.032 Uiso calc U . R 1 . .
C C10 -0.0992(3) 0.3685(2) 0.3792(3) 0.0309(9) Uani d . . . 1 . .
H H10A -0.0842 0.4064 0.4193 0.037 Uiso calc U . R 1 . .
H H10B -0.1684 0.3431 0.3998 0.037 Uiso calc U . R 1 . .
C C11 -0.2023(3) 0.19990(19) 0.1580(2) 0.0222(8) Uani d . . . 1 . .
H H11A -0.2582 0.2367 0.1466 0.033 Uiso calc U . R 1 . .
H H11B -0.2225 0.1777 0.2119 0.033 Uiso calc U . R 1 . .
H H11C -0.2054 0.1664 0.1119 0.033 Uiso calc U . R 1 . .
C C12 0.0075(3) 0.17058(19) 0.1730(3) 0.0238(8) Uani d . . . 1 . .
H H12A 0.0012 0.1408 0.1232 0.036 Uiso calc U . R 1 . .
H H12B -0.0113 0.1446 0.2245 0.036 Uiso calc U . R 1 . .
H H12C 0.0875 0.1883 0.1772 0.036 Uiso calc U . R 1 . .
C C13 -0.2341(3) 0.43079(19) 0.1251(3) 0.0390(10) Uani d . . . 1 . .
H H13A -0.2459 0.4375 0.0639 0.058 Uiso calc U . R 1 . .
H H13B -0.1908 0.4696 0.1485 0.058 Uiso calc U . R 1 . .
H H13C -0.3103 0.4273 0.1534 0.058 Uiso calc U . R 1 . .
O O14 0.1097(2) 0.36587(13) 0.37385(16) 0.0249(6) Uani d . . . 1 . .
C C15 0.2107(3) 0.33824(19) 0.3964(3) 0.0262(8) Uani d . . . 1 . .
O O16 0.2231(2) 0.27869(13) 0.41720(17) 0.0318(6) Uani d . . . 1 . .
C C17 0.3104(3) 0.38753(17) 0.3947(3) 0.0222(7) Uani d . . . 1 . .
C C18 0.4222(3) 0.36405(19) 0.4130(2) 0.0264(9) Uani d . . . 1 . .
H H18 0.4331 0.3174 0.427 0.032 Uiso calc U . R 1 . .
C C19 0.5180(3) 0.40705(19) 0.4114(2) 0.0273(9) Uani d . . . 1 . .
H H19 0.5944 0.3903 0.4227 0.033 Uiso calc U . R 1 . .
C C20 0.4996(3) 0.47510(17) 0.3927(3) 0.0257(8) Uani d . . . 1 . .
C C21 0.3897(3) 0.5001(2) 0.3740(3) 0.0333(10) Uani d . . . 1 . .
H H21 0.3795 0.5469 0.3606 0.04 Uiso calc U . R 1 . .
C C22 0.2941(3) 0.45621(19) 0.3750(3) 0.0306(10) Uani d . . . 1 . .
H H22 0.2181 0.4729 0.3622 0.037 Uiso calc U . R 1 . .
Br Br23 0.62999(3) 0.53552(2) 0.39267(3) 0.03430(11) Uani d . . . 1 . .
C C31 0.2767(3) 0.31878(17) 0.6276(3) 0.0225(8) Uani d . . . 1 . .
H H31 0.282 0.2905 0.5748 0.027 Uiso calc U . R 1 . .
C C32 0.2689(3) 0.27302(17) 0.7037(2) 0.0166(7) Uani d . . . 1 . .
H H32 0.3222 0.236 0.7072 0.02 Uiso calc U . R 1 . .
C C33 0.1921(3) 0.28091(16) 0.7665(2) 0.0154(7) Uani d . . . 1 . .
C C34 0.1826(3) 0.23229(17) 0.8412(2) 0.0141(7) Uani d . . . 1 . .
C C35 0.2100(3) 0.27334(18) 0.9218(2) 0.0194(8) Uani d . . . 1 . .
H H35A 0.1902 0.2456 0.9724 0.023 Uiso calc U . R 1 . .
H H35B 0.2949 0.2832 0.9237 0.023 Uiso calc U . R 1 . .
C C36 0.1431(3) 0.33927(17) 0.9253(2) 0.0198(7) Uani d . . . 1 . .
H H36 0.1352 0.3609 0.9791 0.024 Uiso calc U . R 1 . .
C C37 0.0946(3) 0.36926(17) 0.8588(2) 0.0180(7) Uani d . . . 1 . .
C C38 0.1084(3) 0.34074(16) 0.7699(2) 0.0171(7) Uani d . . . 1 . .
H H38 0.0299 0.3237 0.7515 0.021 Uiso calc U . R 1 . .
C C39 0.1451(3) 0.39689(17) 0.7068(2) 0.0201(7) Uani d . . . 1 . .
H H39A 0.0807 0.4303 0.7008 0.024 Uiso calc U . R 1 . .
H H39B 0.2145 0.4212 0.7292 0.024 Uiso calc U . R 1 . .
C C40 0.1737(3) 0.36667(17) 0.6205(3) 0.0225(8) Uani d . . . 1 . .
H H40A 0.1048 0.3416 0.5985 0.027 Uiso calc U . R 1 . .
H H40B 0.1924 0.4037 0.5799 0.027 Uiso calc U . R 1 . .
C C41 0.2665(3) 0.17136(17) 0.8354(2) 0.0181(7) Uani d . . . 1 . .
H H41A 0.2476 0.1443 0.7849 0.027 Uiso calc U . R 1 . .
H H41B 0.2583 0.143 0.8864 0.027 Uiso calc U . R 1 . .
H H41C 0.3472 0.1879 0.8312 0.027 Uiso calc U . R 1 . .
C C42 0.0578(3) 0.20337(17) 0.8478(2) 0.0191(8) Uani d . . . 1 . .
H H42A 0.0384 0.179 0.7952 0.029 Uiso calc U . R 1 . .
H H42B 0.0022 0.2408 0.8562 0.029 Uiso calc U . R 1 . .
H H42C 0.0533 0.1719 0.896 0.029 Uiso calc U . R 1 . .
C C43 0.0251(3) 0.43392(17) 0.8678(3) 0.0253(9) Uani d . . . 1 . .
H H43A 0.0728 0.4727 0.8493 0.038 Uiso calc U . R 1 . .
H H43B 0.0026 0.4401 0.9275 0.038 Uiso calc U . R 1 . .
H H43C -0.0454 0.4311 0.8325 0.038 Uiso calc U . R 1 . .
O O44 0.38222(18) 0.36223(12) 0.63459(18) 0.0219(5) Uani d . . . 1 . .
C C45 0.4845(3) 0.33402(19) 0.6119(2) 0.0223(8) Uani d . . . 1 . .
O O46 0.4949(2) 0.27547(13) 0.58793(17) 0.0280(6) Uani d . . . 1 . .
C C47 0.5825(3) 0.38313(17) 0.6185(2) 0.0221(8) Uani d . . . 1 . .
C C48 0.6921(3) 0.3626(2) 0.5897(2) 0.0246(8) Uani d . . . 1 . .
H H48 0.7018 0.3182 0.5667 0.03 Uiso calc U . R 1 . .
C C49 0.7867(3) 0.40598(19) 0.5943(2) 0.0255(8) Uani d . . . 1 . .
H H49 0.8618 0.3913 0.5761 0.031 Uiso calc U . R 1 . .
C C50 0.7708(3) 0.47134(18) 0.6257(3) 0.0238(7) Uani d . . . 1 . .
C C51 0.6627(3) 0.4928(2) 0.6536(3) 0.0295(9) Uani d . . . 1 . .
H H51 0.6526 0.5378 0.6748 0.035 Uiso calc U . R 1 . .
C C52 0.5690(3) 0.44844(19) 0.6505(2) 0.0257(9) Uani d . . . 1 . .
H H52 0.4946 0.4628 0.6705 0.031 Uiso calc U . R 1 . .
Br Br53 0.89889(3) 0.53261(2) 0.62842(3) 0.03385(11) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O14 . 1.474(4) ?
C1 C2 . 1.502(5) ?
C1 C10 . 1.509(5) ?
C1 H1 . 1.0 ?
C2 C3 . 1.331(5) ?
C2 H2 . 0.95 ?
C3 C8 . 1.518(5) ?
C3 C4 . 1.527(5) ?
C4 C12 . 1.521(5) ?
C4 C5 . 1.524(5) ?
C4 C11 . 1.541(4) ?
C5 C6 . 1.499(5) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.329(5) ?
C6 H6 . 0.95 ?
C7 C8 . 1.508(5) ?
C7 C13 . 1.517(5) ?
C8 C9 . 1.532(5) ?
C8 H8 . 1.0 ?
C9 C10 . 1.514(6) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
O14 C15 . 1.323(4) ?
C15 O16 . 1.222(4) ?
C15 C17 . 1.494(5) ?
C17 C18 . 1.389(5) ?
C17 C22 . 1.395(5) ?
C18 C19 . 1.382(5) ?
C18 H18 . 0.95 ?
C19 C20 . 1.383(5) ?
C19 H19 . 0.95 ?
C20 C21 . 1.379(5) ?
C20 Br23 . 1.904(3) ?
C21 C22 . 1.391(5) ?
C21 H21 . 0.95 ?
C22 H22 . 0.95 ?
C31 O44 . 1.481(4) ?
C31 C32 . 1.498(5) ?
C31 C40 . 1.510(5) ?
C31 H31 . 1.0 ?
C32 C33 . 1.331(5) ?
C32 H32 . 0.95 ?
C33 C38 . 1.516(4) ?
C33 C34 . 1.517(5) ?
C34 C35 . 1.533(5) ?
C34 C41 . 1.536(4) ?
C34 C42 . 1.538(4) ?
C35 C36 . 1.503(5) ?
C35 H35A . 0.99 ?
C35 H35B . 0.99 ?
C36 C37 . 1.321(5) ?
C36 H36 . 0.95 ?
C37 C43 . 1.503(5) ?
C37 C38 . 1.514(5) ?
C38 C39 . 1.541(4) ?
C38 H38 . 1.0 ?
C39 C40 . 1.516(5) ?
C39 H39A . 0.99 ?
C39 H39B . 0.99 ?
C40 H40A . 0.99 ?
C40 H40B . 0.99 ?
C41 H41A . 0.98 ?
C41 H41B . 0.98 ?
C41 H41C . 0.98 ?
C42 H42A . 0.98 ?
C42 H42B . 0.98 ?
C42 H42C . 0.98 ?
C43 H43A . 0.98 ?
C43 H43B . 0.98 ?
C43 H43C . 0.98 ?
O44 C45 . 1.342(4) ?
C45 O46 . 1.215(4) ?
C45 C47 . 1.481(5) ?
C47 C52 . 1.385(5) ?
C47 C48 . 1.391(5) ?
C48 C49 . 1.378(5) ?
C48 H48 . 0.95 ?
C49 C50 . 1.386(5) ?
C49 H49 . 0.95 ?
C50 C51 . 1.378(5) ?
C50 Br53 . 1.894(3) ?
C51 C52 . 1.381(5) ?
C51 H51 . 0.95 ?
C52 H52 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O14 C1 C2 . . 110.4(3) ?
O14 C1 C10 . . 106.4(3) ?
C2 C1 C10 . . 112.1(3) ?
O14 C1 H1 . . 109.3 ?
C2 C1 H1 . . 109.3 ?
C10 C1 H1 . . 109.3 ?
C3 C2 C1 . . 123.9(3) ?
C3 C2 H2 . . 118.0 ?
C1 C2 H2 . . 118.0 ?
C2 C3 C8 . . 122.4(3) ?
C2 C3 C4 . . 123.4(3) ?
C8 C3 C4 . . 114.2(3) ?
C12 C4 C5 . . 108.6(3) ?
C12 C4 C3 . . 113.4(3) ?
C5 C4 C3 . . 106.8(3) ?
C12 C4 C11 . . 107.9(3) ?
C5 C4 C11 . . 110.2(3) ?
C3 C4 C11 . . 110.0(3) ?
C6 C5 C4 . . 113.0(3) ?
C6 C5 H5A . . 109.0 ?
C4 C5 H5A . . 109.0 ?
C6 C5 H5B . . 109.0 ?
C4 C5 H5B . . 109.0 ?
H5A C5 H5B . . 107.8 ?
C7 C6 C5 . . 123.6(3) ?
C7 C6 H6 . . 118.2 ?
C5 C6 H6 . . 118.2 ?
C6 C7 C8 . . 122.4(3) ?
C6 C7 C13 . . 120.0(4) ?
C8 C7 C13 . . 117.6(4) ?
C7 C8 C3 . . 112.0(3) ?
C7 C8 C9 . . 111.2(3) ?
C3 C8 C9 . . 111.3(3) ?
C7 C8 H8 . . 107.4 ?
C3 C8 H8 . . 107.4 ?
C9 C8 H8 . . 107.4 ?
C10 C9 C8 . . 110.3(3) ?
C10 C9 H9A . . 109.6 ?
C8 C9 H9A . . 109.6 ?
C10 C9 H9B . . 109.6 ?
C8 C9 H9B . . 109.6 ?
H9A C9 H9B . . 108.1 ?
C1 C10 C9 . . 111.1(3) ?
C1 C10 H10A . . 109.4 ?
C9 C10 H10A . . 109.4 ?
C1 C10 H10B . . 109.4 ?
C9 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
C4 C11 H11A . . 109.5 ?
C4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C4 C12 H12A . . 109.5 ?
C4 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C4 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C7 C13 H13A . . 109.5 ?
C7 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C7 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C15 O14 C1 . . 117.0(3) ?
O16 C15 O14 . . 124.4(3) ?
O16 C15 C17 . . 122.4(3) ?
O14 C15 C17 . . 113.2(3) ?
C18 C17 C22 . . 119.3(3) ?
C18 C17 C15 . . 118.9(3) ?
C22 C17 C15 . . 121.9(3) ?
C19 C18 C17 . . 121.5(3) ?
C19 C18 H18 . . 119.3 ?
C17 C18 H18 . . 119.3 ?
C18 C19 C20 . . 118.3(3) ?
C18 C19 H19 . . 120.9 ?
C20 C19 H19 . . 120.9 ?
C21 C20 C19 . . 121.7(3) ?
C21 C20 Br23 . . 119.4(3) ?
C19 C20 Br23 . . 118.9(3) ?
C20 C21 C22 . . 119.5(4) ?
C20 C21 H21 . . 120.2 ?
C22 C21 H21 . . 120.2 ?
C21 C22 C17 . . 119.7(3) ?
C21 C22 H22 . . 120.1 ?
C17 C22 H22 . . 120.1 ?
O44 C31 C32 . . 109.5(3) ?
O44 C31 C40 . . 106.4(3) ?
C32 C31 C40 . . 112.7(3) ?
O44 C31 H31 . . 109.4 ?
C32 C31 H31 . . 109.4 ?
C40 C31 H31 . . 109.4 ?
C33 C32 C31 . . 124.2(3) ?
C33 C32 H32 . . 117.9 ?
C31 C32 H32 . . 117.9 ?
C32 C33 C38 . . 122.1(3) ?
C32 C33 C34 . . 123.3(3) ?
C38 C33 C34 . . 114.5(3) ?
C33 C34 C35 . . 107.1(3) ?
C33 C34 C41 . . 113.5(3) ?
C35 C34 C41 . . 109.3(3) ?
C33 C34 C42 . . 110.5(3) ?
C35 C34 C42 . . 109.2(3) ?
C41 C34 C42 . . 107.2(3) ?
C36 C35 C34 . . 112.3(3) ?
C36 C35 H35A . . 109.2 ?
C34 C35 H35A . . 109.2 ?
C36 C35 H35B . . 109.2 ?
C34 C35 H35B . . 109.2 ?
H35A C35 H35B . . 107.9 ?
C37 C36 C35 . . 124.6(3) ?
C37 C36 H36 . . 117.7 ?
C35 C36 H36 . . 117.7 ?
C36 C37 C43 . . 121.5(3) ?
C36 C37 C38 . . 121.5(3) ?
C43 C37 C38 . . 117.0(3) ?
C37 C38 C33 . . 112.6(3) ?
C37 C38 C39 . . 111.0(3) ?
C33 C38 C39 . . 111.1(3) ?
C37 C38 H38 . . 107.3 ?
C33 C38 H38 . . 107.3 ?
C39 C38 H38 . . 107.3 ?
C40 C39 C38 . . 110.8(3) ?
C40 C39 H39A . . 109.5 ?
C38 C39 H39A . . 109.5 ?
C40 C39 H39B . . 109.5 ?
C38 C39 H39B . . 109.5 ?
H39A C39 H39B . . 108.1 ?
C31 C40 C39 . . 110.2(3) ?
C31 C40 H40A . . 109.6 ?
C39 C40 H40A . . 109.6 ?
C31 C40 H40B . . 109.6 ?
C39 C40 H40B . . 109.6 ?
H40A C40 H40B . . 108.1 ?
C34 C41 H41A . . 109.5 ?
C34 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C34 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C34 C42 H42A . . 109.5 ?
C34 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C34 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C37 C43 H43A . . 109.5 ?
C37 C43 H43B . . 109.5 ?
H43A C43 H43B . . 109.5 ?
C37 C43 H43C . . 109.5 ?
H43A C43 H43C . . 109.5 ?
H43B C43 H43C . . 109.5 ?
C45 O44 C31 . . 116.9(3) ?
O46 C45 O44 . . 123.9(3) ?
O46 C45 C47 . . 124.3(3) ?
O44 C45 C47 . . 111.8(3) ?
C52 C47 C48 . . 119.1(3) ?
C52 C47 C45 . . 122.9(3) ?
C48 C47 C45 . . 118.0(3) ?
C49 C48 C47 . . 120.7(4) ?
C49 C48 H48 . . 119.7 ?
C47 C48 H48 . . 119.7 ?
C48 C49 C50 . . 119.2(3) ?
C48 C49 H49 . . 120.4 ?
C50 C49 H49 . . 120.4 ?
C51 C50 C49 . . 120.9(3) ?
C51 C50 Br53 . . 119.4(3) ?
C49 C50 Br53 . . 119.6(3) ?
C50 C51 C52 . . 119.4(4) ?
C50 C51 H51 . . 120.3 ?
C52 C51 H51 . . 120.3 ?
C51 C52 C47 . . 120.7(3) ?
C51 C52 H52 . . 119.7 ?
C47 C52 H52 . . 119.7 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O14 C1 C2 C3 . . . . -107.7(4) ?
C10 C1 C2 C3 . . . . 10.8(5) ?
C1 C2 C3 C8 . . . . 4.2(5) ?
C1 C2 C3 C4 . . . . -175.9(3) ?
C2 C3 C4 C12 . . . . 0.7(5) ?
C8 C3 C4 C12 . . . . -179.5(3) ?
C2 C3 C4 C5 . . . . -118.9(3) ?
C8 C3 C4 C5 . . . . 61.0(3) ?
C2 C3 C4 C11 . . . . 121.6(4) ?
C8 C3 C4 C11 . . . . -58.6(4) ?
C12 C4 C5 C6 . . . . -171.0(3) ?
C3 C4 C5 C6 . . . . -48.4(3) ?
C11 C4 C5 C6 . . . . 71.1(4) ?
C4 C5 C6 C7 . . . . 19.3(5) ?
C5 C6 C7 C8 . . . . 2.8(5) ?
C5 C6 C7 C13 . . . . -177.8(3) ?
C6 C7 C8 C3 . . . . 7.6(4) ?
C13 C7 C8 C3 . . . . -171.8(3) ?
C6 C7 C8 C9 . . . . 132.8(3) ?
C13 C7 C8 C9 . . . . -46.7(4) ?
C2 C3 C8 C7 . . . . 139.2(3) ?
C4 C3 C8 C7 . . . . -40.6(4) ?
C2 C3 C8 C9 . . . . 14.1(5) ?
C4 C3 C8 C9 . . . . -165.8(3) ?
C7 C8 C9 C10 . . . . -172.1(3) ?
C3 C8 C9 C10 . . . . -46.5(4) ?
O14 C1 C10 C9 . . . . 77.1(4) ?
C2 C1 C10 C9 . . . . -43.8(4) ?
C8 C9 C10 C1 . . . . 62.9(4) ?
C2 C1 O14 C15 . . . . -77.3(4) ?
C10 C1 O14 C15 . . . . 160.8(3) ?
C1 O14 C15 O16 . . . . 2.2(6) ?
C1 O14 C15 C17 . . . . -177.4(3) ?
O16 C15 C17 C18 . . . . 3.5(6) ?
O14 C15 C17 C18 . . . . -176.9(3) ?
O16 C15 C17 C22 . . . . -176.7(4) ?
O14 C15 C17 C22 . . . . 2.9(6) ?
C22 C17 C18 C19 . . . . -0.7(6) ?
C15 C17 C18 C19 . . . . 179.2(4) ?
C17 C18 C19 C20 . . . . 1.5(6) ?
C18 C19 C20 C21 . . . . -1.6(6) ?
C18 C19 C20 Br23 . . . . 178.6(3) ?
C19 C20 C21 C22 . . . . 0.9(6) ?
Br23 C20 C21 C22 . . . . -179.3(3) ?
C20 C21 C22 C17 . . . . -0.1(6) ?
C18 C17 C22 C21 . . . . 0.0(6) ?
C15 C17 C22 C21 . . . . -179.9(4) ?
O44 C31 C32 C33 . . . . 106.9(4) ?
C40 C31 C32 C33 . . . . -11.3(5) ?
C31 C32 C33 C38 . . . . -3.9(5) ?
C31 C32 C33 C34 . . . . 177.4(3) ?
C32 C33 C34 C35 . . . . 118.3(3) ?
C38 C33 C34 C35 . . . . -60.5(3) ?
C32 C33 C34 C41 . . . . -2.4(4) ?
C38 C33 C34 C41 . . . . 178.8(3) ?
C32 C33 C34 C42 . . . . -122.9(3) ?
C38 C33 C34 C42 . . . . 58.3(4) ?
C33 C34 C35 C36 . . . . 48.4(3) ?
C41 C34 C35 C36 . . . . 171.7(3) ?
C42 C34 C35 C36 . . . . -71.3(3) ?
C34 C35 C36 C37 . . . . -19.2(5) ?
C35 C36 C37 C43 . . . . 177.7(3) ?
C35 C36 C37 C38 . . . . -3.5(5) ?
C36 C37 C38 C33 . . . . -6.1(4) ?
C43 C37 C38 C33 . . . . 172.8(3) ?
C36 C37 C38 C39 . . . . -131.4(3) ?
C43 C37 C38 C39 . . . . 47.5(4) ?
C32 C33 C38 C37 . . . . -139.4(3) ?
C34 C33 C38 C37 . . . . 39.4(4) ?
C32 C33 C38 C39 . . . . -14.2(4) ?
C34 C33 C38 C39 . . . . 164.6(3) ?
C37 C38 C39 C40 . . . . 172.8(3) ?
C33 C38 C39 C40 . . . . 46.7(4) ?
O44 C31 C40 C39 . . . . -76.3(4) ?
C32 C31 C40 C39 . . . . 43.7(4) ?
C38 C39 C40 C31 . . . . -62.7(3) ?
C32 C31 O44 C45 . . . . 80.8(4) ?
C40 C31 O44 C45 . . . . -157.1(3) ?
C31 O44 C45 O46 . . . . -1.5(5) ?
C31 O44 C45 C47 . . . . 177.8(3) ?
O46 C45 C47 C52 . . . . -176.3(4) ?
O44 C45 C47 C52 . . . . 4.4(5) ?
O46 C45 C47 C48 . . . . 4.8(6) ?
O44 C45 C47 C48 . . . . -174.4(3) ?
C52 C47 C48 C49 . . . . 1.2(5) ?
C45 C47 C48 C49 . . . . -179.9(3) ?
C47 C48 C49 C50 . . . . -1.9(6) ?
C48 C49 C50 C51 . . . . 1.2(6) ?
C48 C49 C50 Br53 . . . . -177.7(3) ?
C49 C50 C51 C52 . . . . 0.2(6) ?
Br53 C50 C51 C52 . . . . 179.1(3) ?
C50 C51 C52 C47 . . . . -1.0(6) ?
C48 C47 C52 C51 . . . . 0.3(5) ?
C45 C47 C52 C51 . . . . -178.6(3) ?

