# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_zhangyu_181113
_audit_block_doi                 10.5517/ccdc.csd.cc2jcf2f
_database_code_depnum_ccdc_archive 'CCDC 2334674'
loop_
_audit_author_name
_audit_author_address
zhangyu
;Sun Yat sen University
China
;
_audit_update_record             
;
2024-02-22 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_audit_creation_date             2018-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 O3'
_chemical_formula_sum            'C17 H16 O3'
_chemical_formula_weight         268.30
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0416(3)
_cell_length_b                   20.2173(5)
_cell_length_c                   22.2247(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4062.6(2)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    15250
_cell_measurement_temperature    99.97(13)
_cell_measurement_theta_max      76.5610
_cell_measurement_theta_min      2.8970
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1535
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32061
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.093
_diffrn_reflns_theta_min         2.955
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  28.00   0.50    0.07    --  -46.62  29.00 172.00  178
  2  ω   -114.00 -25.00   0.50    0.40    -- -100.00  29.00 172.00  178
  3  ω   -109.00 -27.00   0.50    0.40    -- -100.00  99.00  -1.00  164
  4  ω     34.00 111.00   0.50    0.40    --  107.00-111.00 164.00  154
  5  ω   -119.00 -71.00   0.50    0.07    --  -46.62-125.00  90.00   96
  6  ω   -119.00 -71.00   0.50    0.07    --  -46.62-125.00 120.00   96
  7  ω     32.00 120.00   0.50    0.07    --   46.62  38.00 -90.00  176
  8  ω    -25.00  63.00   0.50    0.07    --   46.62 -57.00 -30.00  176
  9  ω     92.00 178.00   0.50    0.40    --  107.00  30.00 -60.00  172
 10  ω     88.00 178.00   0.50    0.40    --  107.00  99.00  -1.00  180
 11  ω     34.00 109.00   0.50    0.40    --  107.00 -94.00-180.00  150
 12  ω     32.00 123.00   0.50    0.40    --  107.00 -30.00 150.00  182
 13  ω     34.00 131.00   0.50    0.40    --  107.00 -77.00  60.00  194
 14  ω     34.00 117.00   0.50    0.40    --  107.00-125.00-150.00  166
 15  ω     34.00 117.00   0.50    0.40    --  107.00-125.00 -30.00  166
 16  ω     92.00 178.00   0.50    0.40    --  107.00  30.00   0.00  172
 17  ω     35.00 122.00   0.50    0.40    --  107.00 -45.00 150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0019858000
_diffrn_orient_matrix_UB_12      0.0418666000
_diffrn_orient_matrix_UB_13      -0.0578896000
_diffrn_orient_matrix_UB_21      0.0641626000
_diffrn_orient_matrix_UB_22      -0.0588013000
_diffrn_orient_matrix_UB_23      -0.0355859000
_diffrn_orient_matrix_UB_31      -0.1577914000
_diffrn_orient_matrix_UB_32      -0.0244457000
_diffrn_orient_matrix_UB_33      -0.0137185000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                7119
_reflns_number_total             7974
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 2550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         7974
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0734
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0790P)²+6.6155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1726
_refine_ls_wR_factor_ref         0.2089
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00S(H00A,H00B), C014(H01E,H01F), C01B(H01R,H01S)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00H(H00H), C00I(H00I), C00N(H00N), C00P(H00P), C00T(H00T),
 C00U(H00U), C00W(H00W), C011(H011), C012(H012), C016(H016), C017(H017),
 C019(H019), C01A(H01A), C01C(H01G), C01E(H01H), C01G(H01M), C01H(H01N),
 C01I(H01T), C01J(H01J), C01L(H01X)
2.c Idealised Me refined as rotating group:
 C00Z(H00C,H00D,H00F), C01F(H01I,H01K,H01L), C01K(H01U,H01V,H01W), C01M(H01Y,H,
 HA), C01N(H01B,H01C,H01D), C01O(H01O,H01P,H01Q)
2.d Idealised tetrahedral OH refined as rotating group:
 O004(H004), O005(H005), O006(H006)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.8187(5) 0.76116(18) 0.31296(16) 0.0284(8) Uani 1 1 d . . . . .
O002 O 0.5433(5) 0.48931(19) 0.39086(17) 0.0289(8) Uani 1 1 d . . . . .
O003 O 0.7657(5) 0.5143(2) 0.18591(18) 0.0333(9) Uani 1 1 d . . . . .
O004 O 0.3261(5) 0.7970(2) 0.38885(18) 0.0372(10) Uani 1 1 d . . . . .
H004 H 0.240827 0.788002 0.379353 0.056 Uiso 1 1 calc GR . . . .
O005 O 0.0480(5) 0.4074(2) 0.41303(19) 0.0356(10) Uani 1 1 d . . . . .
H005 H -0.030140 0.409893 0.394442 0.053 Uiso 1 1 calc GR . . . .
O006 O 1.2644(5) 0.59407(19) 0.16499(19) 0.0345(9) Uani 1 1 d . . . . .
H006 H 1.347873 0.578661 0.161637 0.052 Uiso 1 1 calc GR . . . .
O007 O 1.0419(5) 0.7706(2) 0.34786(18) 0.0364(10) Uani 1 1 d . . . . .
O008 O 0.7632(5) 0.4450(2) 0.3932(2) 0.0396(10) Uani 1 1 d . . . . .
O009 O 0.5501(6) 0.5446(2) 0.1504(2) 0.0420(11) Uani 1 1 d . . . . .
C00A C 0.6644(7) 0.7485(3) 0.3152(2) 0.0261(11) Uani 1 1 d . . . . .
C00B C 0.9112(8) 0.7598(3) 0.3603(2) 0.0308(13) Uani 1 1 d . . . . .
C00C C 0.5757(6) 0.7815(3) 0.3553(2) 0.0248(11) Uani 1 1 d . . . . .
C00D C 0.4207(6) 0.7680(3) 0.3497(2) 0.0255(11) Uani 1 1 d . . . . .
C00E C 0.6157(7) 0.7058(3) 0.2708(2) 0.0283(12) Uani 1 1 d . . . . .
H00E H 0.682097 0.685241 0.244943 0.034 Uiso 1 1 calc R . . . .
C00F C 0.7611(7) 0.8113(3) 0.4363(2) 0.0269(12) Uani 1 1 d . . . . .
C00G C 0.9589(8) 0.6277(3) 0.1660(2) 0.0318(13) Uani 1 1 d . . . . .
C00H C 1.0264(8) 0.6798(3) 0.1971(2) 0.0316(13) Uani 1 1 d . . . . .
H00H H 1.104932 0.671113 0.222917 0.038 Uiso 1 1 calc R . . . .
C00I C 0.4652(8) 0.6947(3) 0.2661(2) 0.0327(13) Uani 1 1 d . . . . .
H00I H 0.428523 0.666230 0.236823 0.039 Uiso 1 1 calc R . . . .
C00J C 0.6338(8) 0.8265(3) 0.4025(2) 0.0301(13) Uani 1 1 d . . . . .
C00K C 0.3927(7) 0.4911(3) 0.3794(2) 0.0271(11) Uani 1 1 d . . . . .
C00L C 0.1455(7) 0.4533(3) 0.3911(2) 0.0280(11) Uani 1 1 d . . . . .
C00M C 1.1660(7) 0.5440(3) 0.1764(2) 0.0300(12) Uani 1 1 d . . . . .
C00N C 0.2770(8) 0.3763(3) 0.4965(3) 0.0341(14) Uani 1 1 d . . . . .
H00N H 0.197582 0.402791 0.507832 0.041 Uiso 1 1 calc R . . . .
C00O C 0.2957(6) 0.4453(3) 0.4041(2) 0.0244(11) Uani 1 1 d . . . . .
C00P C 0.5588(8) 0.8862(3) 0.4137(3) 0.0334(13) Uani 1 1 d . . . . .
H00P H 0.474452 0.896531 0.391634 0.040 Uiso 1 1 calc R . . . .
C00Q C 0.4706(7) 0.3506(3) 0.4256(2) 0.0293(13) Uani 1 1 d . . . . .
C00R C 0.6317(7) 0.4357(3) 0.3843(2) 0.0314(13) Uani 1 1 d . . . . .
C00S C 0.7627(8) 0.6834(3) 0.4302(2) 0.0321(13) Uani 1 1 d . . . . .
H00A H 0.752063 0.672791 0.472559 0.039 Uiso 1 1 calc R . . . .
H00B H 0.664520 0.690631 0.413846 0.039 Uiso 1 1 calc R . . . .
C00T C 0.3709(8) 0.7258(3) 0.3050(2) 0.0336(13) Uani 1 1 d . . . . .
H00T H 0.269772 0.718411 0.301362 0.040 Uiso 1 1 calc R . . . .
C00U C 0.0965(8) 0.5059(3) 0.3556(3) 0.0343(14) Uani 1 1 d . . . . .
H00U H -0.003721 0.510165 0.346902 0.041 Uiso 1 1 calc R . . . .
C00V C 1.0137(7) 0.5594(3) 0.1763(2) 0.0270(12) Uani 1 1 d . . . . .
C00W C 1.1187(8) 0.4297(3) 0.1966(3) 0.0368(14) Uani 1 1 d . . . . .
H00W H 1.153513 0.387269 0.204198 0.044 Uiso 1 1 calc R . . . .
C00X C 0.3498(7) 0.3893(3) 0.4422(2) 0.0279(12) Uani 1 1 d . . . . .
C00Y C 0.8555(8) 0.7488(3) 0.4237(2) 0.0309(13) Uani 1 1 d . . . . .
C00Z C 0.9896(8) 0.7437(3) 0.4651(2) 0.0358(14) Uani 1 1 d . . . . .
H00C H 1.047471 0.705788 0.454146 0.054 Uiso 1 1 calc GR . . . .
H00D H 0.957067 0.739351 0.506018 0.054 Uiso 1 1 calc GR . . . .
H00F H 1.048783 0.782941 0.461174 0.054 Uiso 1 1 calc GR . . . .
C010 C 0.8404(8) 0.6411(3) 0.1266(2) 0.0318(13) Uani 1 1 d . . . . .
C011 C 1.2154(8) 0.4802(3) 0.1868(3) 0.0390(15) Uani 1 1 d . . . . .
H011 H 1.316452 0.471741 0.187176 0.047 Uiso 1 1 calc R . . . .
C012 C 0.7934(8) 0.7063(3) 0.1197(3) 0.0365(14) Uani 1 1 d . . . . .
H012 H 0.714775 0.715727 0.094090 0.044 Uiso 1 1 calc R . . . .
C013 C 0.6856(8) 0.5461(3) 0.1437(3) 0.0338(13) Uani 1 1 d . . . . .
C014 C 0.4774(8) 0.3672(3) 0.3099(2) 0.0346(14) Uani 1 1 d . . . . .
H01E H 0.460800 0.321803 0.297608 0.042 Uiso 1 1 calc R . . . .
H01F H 0.381400 0.387300 0.316766 0.042 Uiso 1 1 calc R . . . .
C015 C 0.7625(8) 0.5847(3) 0.0931(3) 0.0346(14) Uani 1 1 d . . . . .
C016 C 0.6093(9) 0.9297(3) 0.4571(3) 0.0402(16) Uani 1 1 d . . . . .
H016 H 0.559714 0.969322 0.463578 0.048 Uiso 1 1 calc R . . . .
C017 C 0.9769(9) 0.7444(3) 0.1897(3) 0.0391(16) Uani 1 1 d . . . . .
H017 H 1.021006 0.778650 0.211122 0.047 Uiso 1 1 calc R . . . .
C018 C 0.9204(7) 0.5059(3) 0.1845(2) 0.0300(12) Uani 1 1 d . . . . .
C019 C 0.1949(8) 0.5512(3) 0.3334(3) 0.0332(13) Uani 1 1 d . . . . .
H019 H 0.161186 0.586761 0.310668 0.040 Uiso 1 1 calc R . . . .
C01A C 0.8076(8) 0.8561(3) 0.4800(3) 0.0373(15) Uani 1 1 d . . . . .
H01A H 0.891477 0.846379 0.502551 0.045 Uiso 1 1 calc R . . . .
C01B C 0.8680(8) 0.5422(3) 0.0541(3) 0.0331(13) Uani 1 1 d . . . . .
H01R H 0.887321 0.565989 0.016963 0.040 Uiso 1 1 calc R . . . .
H01S H 0.961336 0.537958 0.075202 0.040 Uiso 1 1 calc R . . . .
C01C C 0.4350(8) 0.2849(3) 0.5156(3) 0.0359(15) Uani 1 1 d . . . . .
H01G H 0.461630 0.248729 0.539038 0.043 Uiso 1 1 calc R . . . .
C01D C 0.5646(8) 0.3672(3) 0.3700(3) 0.0332(13) Uani 1 1 d . . . . .
C01E C 0.3207(8) 0.3250(3) 0.5336(3) 0.0354(14) Uani 1 1 d . . . . .
H01H H 0.273374 0.317693 0.570124 0.043 Uiso 1 1 calc R . . . .
C01F C 0.6957(8) 0.3201(3) 0.3620(3) 0.0394(15) Uani 1 1 d . . . . .
H01I H 0.755576 0.320675 0.397620 0.059 Uiso 1 1 calc GR . . . .
H01K H 0.753966 0.334061 0.328145 0.059 Uiso 1 1 calc GR . . . .
H01L H 0.659828 0.276057 0.355066 0.059 Uiso 1 1 calc GR . . . .
C01G C 0.3463(8) 0.5442(3) 0.3450(3) 0.0333(13) Uani 1 1 d . . . . .
H01M H 0.414155 0.574501 0.329895 0.040 Uiso 1 1 calc R . . . .
C01H C 0.5103(8) 0.2980(3) 0.4633(3) 0.0344(14) Uani 1 1 d . . . . .
H01N H 0.589775 0.271223 0.452603 0.041 Uiso 1 1 calc R . . . .
C01I C 0.9680(8) 0.4422(3) 0.1950(3) 0.0348(13) Uani 1 1 d . . . . .
H01T H 0.900250 0.408154 0.200837 0.042 Uiso 1 1 calc R . . . .
C01J C 0.7327(9) 0.9146(3) 0.4907(3) 0.0410(16) Uani 1 1 d . . . . .
H01J H 0.765403 0.943543 0.520372 0.049 Uiso 1 1 calc R . . . .
C01K C 0.6394(9) 0.6105(3) 0.0509(3) 0.0422(16) Uani 1 1 d . . . . .
H01U H 0.566815 0.634002 0.073996 0.063 Uiso 1 1 calc GR . . . .
H01V H 0.593197 0.573764 0.030895 0.063 Uiso 1 1 calc GR . . . .
H01W H 0.681781 0.639606 0.021441 0.063 Uiso 1 1 calc GR . . . .
C01L C 0.8629(8) 0.7577(3) 0.1507(3) 0.0367(14) Uani 1 1 d . . . . .
H01X H 0.831812 0.801106 0.144899 0.044 Uiso 1 1 calc R . . . .
C01M C 0.8131(9) 0.4730(3) 0.0380(3) 0.0444(17) Uani 1 1 d . . . . .
H01Y H 0.880822 0.452768 0.010301 0.067 Uiso 1 1 calc GR . . . .
H H 0.717092 0.476047 0.019802 0.067 Uiso 1 1 calc GR . . . .
HA H 0.806972 0.446668 0.073878 0.067 Uiso 1 1 calc GR . . . .
C01N C 0.8348(9) 0.6248(3) 0.3977(3) 0.0425(16) Uani 1 1 d . . . . .
H01B H 0.835710 0.633065 0.355128 0.064 Uiso 1 1 calc GR . . . .
H01C H 0.779508 0.585260 0.405741 0.064 Uiso 1 1 calc GR . . . .
H01D H 0.934487 0.619395 0.411750 0.064 Uiso 1 1 calc GR . . . .
C01O C 0.5523(10) 0.4033(4) 0.2593(3) 0.0496(19) Uani 1 1 d . . . . .
H01O H 0.501916 0.394020 0.222269 0.074 Uiso 1 1 calc GR . . . .
H01P H 0.653239 0.388885 0.256384 0.074 Uiso 1 1 calc GR . . . .
H01Q H 0.549760 0.449990 0.267040 0.074 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00A 1.419(7) . ?
O001 C00B 1.344(7) . ?
O002 C00K 1.386(7) . ?
O002 C00R 1.355(7) . ?
O003 C013 1.349(8) . ?
O003 C018 1.409(7) . ?
O004 H004 0.8200 . ?
O004 C00D 1.353(7) . ?
O005 H005 0.8200 . ?
O005 C00L 1.370(7) . ?
O006 H006 0.8200 . ?
O006 C00M 1.371(7) . ?
O007 C00B 1.232(8) . ?
O008 C00R 1.220(8) . ?
O009 C013 1.235(8) . ?
C00A C00C 1.371(8) . ?
C00A C00E 1.383(8) . ?
C00B C00Y 1.514(8) . ?
C00C C00D 1.433(8) . ?
C00C C00J 1.485(8) . ?
C00D C00T 1.384(8) . ?
C00E H00E 0.9300 . ?
C00E C00I 1.383(9) . ?
C00F C00J 1.409(9) . ?
C00F C00Y 1.551(8) . ?
C00F C01A 1.392(8) . ?
C00G C00H 1.399(8) . ?
C00G C00V 1.485(8) . ?
C00G C010 1.410(9) . ?
C00H H00H 0.9300 . ?
C00H C017 1.391(8) . ?
C00I H00I 0.9300 . ?
C00I C00T 1.369(9) . ?
C00J C00P 1.407(8) . ?
C00K C00O 1.388(8) . ?
C00K C01G 1.383(8) . ?
C00L C00O 1.398(8) . ?
C00L C00U 1.398(8) . ?
C00M C00V 1.413(9) . ?
C00M C011 1.383(8) . ?
C00N H00N 0.9300 . ?
C00N C00X 1.398(8) . ?
C00N C01E 1.384(9) . ?
C00O C00X 1.497(8) . ?
C00P H00P 0.9300 . ?
C00P C016 1.383(9) . ?
C00Q C00X 1.393(9) . ?
C00Q C01D 1.537(8) . ?
C00Q C01H 1.401(8) . ?
C00R C01D 1.545(8) . ?
C00S H00A 0.9700 . ?
C00S H00B 0.9700 . ?
C00S C00Y 1.572(9) . ?
C00S C01N 1.535(8) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00U C019 1.369(9) . ?
C00V C018 1.383(8) . ?
C00W H00W 0.9300 . ?
C00W C011 1.361(10) . ?
C00W C01I 1.386(10) . ?
C00Y C00Z 1.525(8) . ?
C00Z H00C 0.9600 . ?
C00Z H00D 0.9600 . ?
C00Z H00F 0.9600 . ?
C010 C012 1.395(8) . ?
C010 C015 1.532(9) . ?
C011 H011 0.9300 . ?
C012 H012 0.9300 . ?
C012 C01L 1.396(9) . ?
C013 C015 1.533(9) . ?
C014 H01E 0.9700 . ?
C014 H01F 0.9700 . ?
C014 C01D 1.551(8) . ?
C014 C01O 1.500(9) . ?
C015 C01B 1.549(9) . ?
C015 C01K 1.547(9) . ?
C016 H016 0.9300 . ?
C016 C01J 1.376(10) . ?
C017 H017 0.9300 . ?
C017 C01L 1.373(10) . ?
C018 C01I 1.379(8) . ?
C019 H019 0.9300 . ?
C019 C01G 1.400(9) . ?
C01A H01A 0.9300 . ?
C01A C01J 1.385(9) . ?
C01B H01R 0.9700 . ?
C01B H01S 0.9700 . ?
C01B C01M 1.527(8) . ?
C01C H01G 0.9300 . ?
C01C C01E 1.372(10) . ?
C01C C01H 1.374(9) . ?
C01D C01F 1.530(9) . ?
C01E H01H 0.9300 . ?
C01F H01I 0.9600 . ?
C01F H01K 0.9600 . ?
C01F H01L 0.9600 . ?
C01G H01M 0.9300 . ?
C01H H01N 0.9300 . ?
C01I H01T 0.9300 . ?
C01J H01J 0.9300 . ?
C01K H01U 0.9600 . ?
C01K H01V 0.9600 . ?
C01K H01W 0.9600 . ?
C01L H01X 0.9300 . ?
C01M H01Y 0.9600 . ?
C01M H 0.9600 . ?
C01M HA 0.9600 . ?
C01N H01B 0.9600 . ?
C01N H01C 0.9600 . ?
C01N H01D 0.9600 . ?
C01O H01O 0.9600 . ?
C01O H01P 0.9600 . ?
C01O H01Q 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00B O001 C00A 125.5(4) . . ?
C00R O002 C00K 125.4(5) . . ?
C013 O003 C018 125.1(5) . . ?
C00D O004 H004 109.5 . . ?
C00L O005 H005 109.5 . . ?
C00M O006 H006 109.5 . . ?
C00C C00A O001 120.7(5) . . ?
C00C C00A C00E 125.5(6) . . ?
C00E C00A O001 113.6(5) . . ?
O001 C00B C00Y 121.6(6) . . ?
O007 C00B O001 114.7(5) . . ?
O007 C00B C00Y 123.6(5) . . ?
C00A C00C C00D 115.1(5) . . ?
C00A C00C C00J 123.3(6) . . ?
C00D C00C C00J 121.6(5) . . ?
O004 C00D C00C 118.7(5) . . ?
O004 C00D C00T 121.5(6) . . ?
C00T C00D C00C 119.9(5) . . ?
C00A C00E H00E 121.0 . . ?
C00I C00E C00A 118.0(5) . . ?
C00I C00E H00E 121.0 . . ?
C00J C00F C00Y 122.1(5) . . ?
C01A C00F C00J 118.5(5) . . ?
C01A C00F C00Y 119.3(6) . . ?
C00H C00G C00V 118.5(6) . . ?
C00H C00G C010 119.6(5) . . ?
C010 C00G C00V 121.8(5) . . ?
C00G C00H H00H 119.7 . . ?
C017 C00H C00G 120.5(6) . . ?
C017 C00H H00H 119.7 . . ?
C00E C00I H00I 120.3 . . ?
C00T C00I C00E 119.4(5) . . ?
C00T C00I H00I 120.3 . . ?
C00F C00J C00C 122.2(5) . . ?
C00P C00J C00C 118.7(6) . . ?
C00P C00J C00F 119.2(5) . . ?
O002 C00K C00O 122.0(5) . . ?
C01G C00K O002 114.8(5) . . ?
C01G C00K C00O 123.0(6) . . ?
O005 C00L C00O 118.3(5) . . ?
O005 C00L C00U 120.8(6) . . ?
C00O C00L C00U 120.9(6) . . ?
O006 C00M C00V 118.0(5) . . ?
O006 C00M C011 120.7(6) . . ?
C011 C00M C00V 121.4(6) . . ?
C00X C00N H00N 119.4 . . ?
C01E C00N H00N 119.4 . . ?
C01E C00N C00X 121.3(6) . . ?
C00K C00O C00L 117.1(5) . . ?
C00K C00O C00X 121.5(5) . . ?
C00L C00O C00X 121.5(5) . . ?
C00J C00P H00P 119.7 . . ?
C016 C00P C00J 120.6(6) . . ?
C016 C00P H00P 119.7 . . ?
C00X C00Q C01D 121.7(5) . . ?
C00X C00Q C01H 117.9(6) . . ?
C01H C00Q C01D 120.3(6) . . ?
O002 C00R C01D 120.5(6) . . ?
O008 C00R O002 115.6(5) . . ?
O008 C00R C01D 123.8(6) . . ?
H00A C00S H00B 107.9 . . ?
C00Y C00S H00A 109.2 . . ?
C00Y C00S H00B 109.2 . . ?
C01N C00S H00A 109.2 . . ?
C01N C00S H00B 109.2 . . ?
C01N C00S C00Y 112.2(5) . . ?
C00D C00T H00T 118.9 . . ?
C00I C00T C00D 122.3(6) . . ?
C00I C00T H00T 118.9 . . ?
C00L C00U H00U 119.8 . . ?
C019 C00U C00L 120.4(6) . . ?
C019 C00U H00U 119.8 . . ?
C00M C00V C00G 122.1(5) . . ?
C018 C00V C00G 123.0(6) . . ?
C018 C00V C00M 114.9(5) . . ?
C011 C00W H00W 120.3 . . ?
C011 C00W C01I 119.4(6) . . ?
C01I C00W H00W 120.3 . . ?
C00N C00X C00O 118.4(5) . . ?
C00Q C00X C00N 119.6(5) . . ?
C00Q C00X C00O 122.0(5) . . ?
C00B C00Y C00F 103.4(4) . . ?
C00B C00Y C00S 112.8(4) . . ?
C00B C00Y C00Z 107.9(5) . . ?
C00F C00Y C00S 112.0(5) . . ?
C00Z C00Y C00F 112.5(5) . . ?
C00Z C00Y C00S 108.3(5) . . ?
C00Y C00Z H00C 109.5 . . ?
C00Y C00Z H00D 109.5 . . ?
C00Y C00Z H00F 109.5 . . ?
H00C C00Z H00D 109.5 . . ?
H00C C00Z H00F 109.5 . . ?
H00D C00Z H00F 109.5 . . ?
C00G C010 C015 120.6(5) . . ?
C012 C010 C00G 118.7(6) . . ?
C012 C010 C015 120.7(6) . . ?
C00M C011 H011 119.4 . . ?
C00W C011 C00M 121.2(7) . . ?
C00W C011 H011 119.4 . . ?
C010 C012 H012 119.6 . . ?
C010 C012 C01L 120.8(6) . . ?
C01L C012 H012 119.6 . . ?
O003 C013 C015 120.6(6) . . ?
O009 C013 O003 115.9(5) . . ?
O009 C013 C015 123.4(6) . . ?
H01E C014 H01F 107.6 . . ?
C01D C014 H01E 108.6 . . ?
C01D C014 H01F 108.6 . . ?
C01O C014 H01E 108.6 . . ?
C01O C014 H01F 108.6 . . ?
C01O C014 C01D 114.6(6) . . ?
C010 C015 C013 103.4(5) . . ?
C010 C015 C01B 113.6(6) . . ?
C010 C015 C01K 112.0(5) . . ?
C013 C015 C01B 114.1(5) . . ?
C013 C015 C01K 106.9(6) . . ?
C01K C015 C01B 106.8(5) . . ?
C00P C016 H016 119.8 . . ?
C01J C016 C00P 120.4(6) . . ?
C01J C016 H016 119.8 . . ?
C00H C017 H017 120.0 . . ?
C01L C017 C00H 120.0(6) . . ?
C01L C017 H017 120.0 . . ?
C00V C018 O003 120.9(5) . . ?
C01I C018 O003 114.7(5) . . ?
C01I C018 C00V 124.3(6) . . ?
C00U C019 H019 120.0 . . ?
C00U C019 C01G 120.1(6) . . ?
C01G C019 H019 120.0 . . ?
C00F C01A H01A 119.1 . . ?
C01J C01A C00F 121.9(6) . . ?
C01J C01A H01A 119.1 . . ?
C015 C01B H01R 108.3 . . ?
C015 C01B H01S 108.3 . . ?
H01R C01B H01S 107.4 . . ?
C01M C01B C015 116.0(6) . . ?
C01M C01B H01R 108.3 . . ?
C01M C01B H01S 108.3 . . ?
C01E C01C H01G 119.8 . . ?
C01E C01C C01H 120.4(6) . . ?
C01H C01C H01G 119.8 . . ?
C00Q C01D C00R 104.3(4) . . ?
C00Q C01D C014 114.3(5) . . ?
C00R C01D C014 112.1(5) . . ?
C01F C01D C00Q 112.7(5) . . ?
C01F C01D C00R 106.1(6) . . ?
C01F C01D C014 107.1(5) . . ?
C00N C01E H01H 120.5 . . ?
C01C C01E C00N 119.0(6) . . ?
C01C C01E H01H 120.5 . . ?
C01D C01F H01I 109.5 . . ?
C01D C01F H01K 109.5 . . ?
C01D C01F H01L 109.5 . . ?
H01I C01F H01K 109.5 . . ?
H01I C01F H01L 109.5 . . ?
H01K C01F H01L 109.5 . . ?
C00K C01G C019 118.5(6) . . ?
C00K C01G H01M 120.8 . . ?
C019 C01G H01M 120.8 . . ?
C00Q C01H H01N 119.2 . . ?
C01C C01H C00Q 121.7(6) . . ?
C01C C01H H01N 119.2 . . ?
C00W C01I H01T 120.6 . . ?
C018 C01I C00W 118.7(6) . . ?
C018 C01I H01T 120.6 . . ?
C016 C01J C01A 119.5(6) . . ?
C016 C01J H01J 120.3 . . ?
C01A C01J H01J 120.3 . . ?
C015 C01K H01U 109.5 . . ?
C015 C01K H01V 109.5 . . ?
C015 C01K H01W 109.5 . . ?
H01U C01K H01V 109.5 . . ?
H01U C01K H01W 109.5 . . ?
H01V C01K H01W 109.5 . . ?
C012 C01L H01X 119.9 . . ?
C017 C01L C012 120.2(5) . . ?
C017 C01L H01X 119.9 . . ?
C01B C01M H01Y 109.5 . . ?
C01B C01M H 109.5 . . ?
C01B C01M HA 109.5 . . ?
H01Y C01M H 109.5 . . ?
H01Y C01M HA 109.5 . . ?
H C01M HA 109.5 . . ?
C00S C01N H01B 109.5 . . ?
C00S C01N H01C 109.5 . . ?
C00S C01N H01D 109.5 . . ?
H01B C01N H01C 109.5 . . ?
H01B C01N H01D 109.5 . . ?
H01C C01N H01D 109.5 . . ?
C014 C01O H01O 109.5 . . ?
C014 C01O H01P 109.5 . . ?
C014 C01O H01Q 109.5 . . ?
H01O C01O H01P 109.5 . . ?
H01O C01O H01Q 109.5 . . ?
H01P C01O H01Q 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
O001 C00A C00C C00D 175.2(4) . . . . ?
O001 C00A C00C C00J -6.5(8) . . . . ?
O001 C00A C00E C00I -174.8(5) . . . . ?
O001 C00B C00Y C00F -65.8(6) . . . . ?
O001 C00B C00Y C00S 55.3(7) . . . . ?
O001 C00B C00Y C00Z 174.8(5) . . . . ?
O002 C00K C00O C00L 177.7(5) . . . . ?
O002 C00K C00O C00X -3.1(8) . . . . ?
O002 C00K C01G C019 -177.3(5) . . . . ?
O002 C00R C01D C00Q -64.1(6) . . . . ?
O002 C00R C01D C014 60.0(7) . . . . ?
O002 C00R C01D C01F 176.6(5) . . . . ?
O003 C013 C015 C010 -65.5(7) . . . . ?
O003 C013 C015 C01B 58.4(7) . . . . ?
O003 C013 C015 C01K 176.2(5) . . . . ?
O003 C018 C01I C00W -177.8(5) . . . . ?
O004 C00D C00T C00I -178.1(5) . . . . ?
O005 C00L C00O C00K 177.5(5) . . . . ?
O005 C00L C00O C00X -1.7(8) . . . . ?
O005 C00L C00U C019 -179.4(5) . . . . ?
O006 C00M C00V C00G -1.7(8) . . . . ?
O006 C00M C00V C018 176.2(5) . . . . ?
O006 C00M C011 C00W -178.1(5) . . . . ?
O007 C00B C00Y C00F 111.5(6) . . . . ?
O007 C00B C00Y C00S -127.4(6) . . . . ?
O007 C00B C00Y C00Z -7.9(7) . . . . ?
O008 C00R C01D C00Q 112.2(6) . . . . ?
O008 C00R C01D C014 -123.6(6) . . . . ?
O008 C00R C01D C01F -7.1(8) . . . . ?
O009 C013 C015 C010 110.8(7) . . . . ?
O009 C013 C015 C01B -125.3(6) . . . . ?
O009 C013 C015 C01K -7.5(8) . . . . ?
C00A O001 C00B O007 178.1(5) . . . . ?
C00A O001 C00B C00Y -4.4(8) . . . . ?
C00A C00C C00D O004 177.9(5) . . . . ?
C00A C00C C00D C00T -1.7(7) . . . . ?
C00A C00C C00J C00F -41.3(8) . . . . ?
C00A C00C C00J C00P 138.6(6) . . . . ?
C00A C00E C00I C00T 0.0(8) . . . . ?
C00B O001 C00A C00C 52.1(7) . . . . ?
C00B O001 C00A C00E -133.3(5) . . . . ?
C00C C00A C00E C00I -0.4(8) . . . . ?
C00C C00D C00T C00I 1.5(8) . . . . ?
C00C C00J C00P C016 -179.7(6) . . . . ?
C00D C00C C00J C00F 136.8(6) . . . . ?
C00D C00C C00J C00P -43.3(7) . . . . ?
C00E C00A C00C C00D 1.2(8) . . . . ?
C00E C00A C00C C00J 179.5(5) . . . . ?
C00E C00I C00T C00D -0.6(8) . . . . ?
C00F C00J C00P C016 0.2(9) . . . . ?
C00F C01A C01J C016 -0.6(10) . . . . ?
C00G C00H C017 C01L -1.3(9) . . . . ?
C00G C00V C018 O003 -2.6(8) . . . . ?
C00G C00V C018 C01I -179.1(5) . . . . ?
C00G C010 C012 C01L 0.6(9) . . . . ?
C00G C010 C015 C013 67.1(7) . . . . ?
C00G C010 C015 C01B -57.1(7) . . . . ?
C00G C010 C015 C01K -178.2(6) . . . . ?
C00H C00G C00V C00M -46.4(8) . . . . ?
C00H C00G C00V C018 135.8(6) . . . . ?
C00H C00G C010 C012 0.0(9) . . . . ?
C00H C00G C010 C015 -178.6(5) . . . . ?
C00H C017 C01L C012 1.9(9) . . . . ?
C00J C00C C00D O004 -0.5(8) . . . . ?
C00J C00C C00D C00T 180.0(5) . . . . ?
C00J C00F C00Y C00B 62.6(7) . . . . ?
C00J C00F C00Y C00S -59.1(7) . . . . ?
C00J C00F C00Y C00Z 178.7(5) . . . . ?
C00J C00F C01A C01J -0.2(9) . . . . ?
C00J C00P C016 C01J -1.0(10) . . . . ?
C00K O002 C00R O008 175.8(5) . . . . ?
C00K O002 C00R C01D -7.6(8) . . . . ?
C00K C00O C00X C00N 133.3(6) . . . . ?
C00K C00O C00X C00Q -45.9(8) . . . . ?
C00L C00O C00X C00N -47.5(7) . . . . ?
C00L C00O C00X C00Q 133.2(6) . . . . ?
C00L C00U C019 C01G 1.7(9) . . . . ?
C00M C00V C018 O003 179.5(5) . . . . ?
C00M C00V C018 C01I 2.9(8) . . . . ?
C00O C00K C01G C019 -1.5(8) . . . . ?
C00O C00L C00U C019 -0.9(8) . . . . ?
C00P C016 C01J C01A 1.2(10) . . . . ?
C00R O002 C00K C00O 51.9(7) . . . . ?
C00R O002 C00K C01G -132.2(5) . . . . ?
C00U C00L C00O C00K -1.0(8) . . . . ?
C00U C00L C00O C00X 179.8(5) . . . . ?
C00U C019 C01G C00K -0.5(9) . . . . ?
C00V C00G C00H C017 -178.8(5) . . . . ?
C00V C00G C010 C012 179.1(6) . . . . ?
C00V C00G C010 C015 0.6(9) . . . . ?
C00V C00M C011 C00W 0.9(9) . . . . ?
C00V C018 C01I C00W -1.1(9) . . . . ?
C00X C00N C01E C01C -2.0(9) . . . . ?
C00X C00Q C01D C00R 62.6(7) . . . . ?
C00X C00Q C01D C014 -60.1(7) . . . . ?
C00X C00Q C01D C01F 177.2(5) . . . . ?
C00X C00Q C01H C01C -0.9(9) . . . . ?
C00Y C00F C00J C00C 4.1(8) . . . . ?
C00Y C00F C00J C00P -175.8(5) . . . . ?
C00Y C00F C01A C01J 176.1(6) . . . . ?
C010 C00G C00H C017 0.4(9) . . . . ?
C010 C00G C00V C00M 134.4(6) . . . . ?
C010 C00G C00V C018 -43.3(8) . . . . ?
C010 C012 C01L C017 -1.5(9) . . . . ?
C010 C015 C01B C01M 159.0(5) . . . . ?
C011 C00M C00V C00G 179.2(5) . . . . ?
C011 C00M C00V C018 -2.8(8) . . . . ?
C011 C00W C01I C018 -1.1(9) . . . . ?
C012 C010 C015 C013 -111.4(6) . . . . ?
C012 C010 C015 C01B 124.4(6) . . . . ?
C012 C010 C015 C01K 3.3(8) . . . . ?
C013 O003 C018 C00V 51.9(8) . . . . ?
C013 O003 C018 C01I -131.2(6) . . . . ?
C013 C015 C01B C01M 40.8(8) . . . . ?
C015 C010 C012 C01L 179.1(5) . . . . ?
C018 O003 C013 O009 175.2(5) . . . . ?
C018 O003 C013 C015 -8.2(8) . . . . ?
C01A C00F C00J C00C -179.7(5) . . . . ?
C01A C00F C00J C00P 0.4(8) . . . . ?
C01A C00F C00Y C00B -113.6(6) . . . . ?
C01A C00F C00Y C00S 124.8(6) . . . . ?
C01A C00F C00Y C00Z 2.5(8) . . . . ?
C01D C00Q C00X C00N -173.4(5) . . . . ?
C01D C00Q C00X C00O 5.8(8) . . . . ?
C01D C00Q C01H C01C 175.2(5) . . . . ?
C01E C00N C00X C00O 179.5(5) . . . . ?
C01E C00N C00X C00Q -1.2(9) . . . . ?
C01E C01C C01H C00Q -2.3(9) . . . . ?
C01G C00K C00O C00L 2.2(8) . . . . ?
C01G C00K C00O C00X -178.6(5) . . . . ?
C01H C00Q C00X C00N 2.6(8) . . . . ?
C01H C00Q C00X C00O -178.1(5) . . . . ?
C01H C00Q C01D C00R -113.4(6) . . . . ?
C01H C00Q C01D C014 123.9(6) . . . . ?
C01H C00Q C01D C01F 1.3(8) . . . . ?
C01H C01C C01E C00N 3.7(9) . . . . ?
C01I C00W C011 C00M 1.1(10) . . . . ?
C01K C015 C01B C01M -77.0(7) . . . . ?
C01N C00S C00Y C00B 44.1(7) . . . . ?
C01N C00S C00Y C00F 160.1(5) . . . . ?
C01N C00S C00Y C00Z -75.2(6) . . . . ?
C01O C014 C01D C00Q 161.6(5) . . . . ?
C01O C014 C01D C00R 43.2(7) . . . . ?
C01O C014 C01D C01F -72.8(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.982
_oxdiff_exptl_absorpt_empirical_full_min 0.324
####################################################################### 
# 
# 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_zhangy_231123_auto
_database_code_depnum_ccdc_archive 'CCDC 2334679'
loop_
_audit_author_name
_audit_author_address
zhangyu
;Sun Yat sen University
China
;
_audit_update_record             
;
2024-02-22 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 O3'
_chemical_formula_sum            'C19 H20 O3'
_chemical_formula_weight         296.35
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     CHO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3390(4)
_cell_length_b                   11.1632(6)
_cell_length_c                   16.2872(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.877(4)
_cell_angle_gamma                90
_cell_volume                     1512.70(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3966
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.5460
_cell_measurement_theta_min      4.7660
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8450
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.502
_diffrn_reflns_theta_min         4.806
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -43.00   0.50    1.03    -- -100.00 116.00  80.00  132
  2  ω   -112.00 -30.00   0.50    1.03    -- -100.00 125.00-120.00  164
  3  ω    -68.00 -31.00   0.50    1.03    -- -100.00  61.00-150.00   74
  4  ω    -62.00 -35.00   0.50    1.03    -- -100.00  61.00-120.00   54
  5  ω    -23.00  28.00   0.50    0.05    --  -44.85  19.00-180.00  102
  6  ω   -116.00 -27.00   0.50    0.05    --  -44.85 -57.00-120.00  178
  7  ω   -116.00 -50.00   0.50    0.05    --  -44.85-167.00-154.00  132
  8  ω   -172.00 -97.00   0.50    1.03    -- -100.00 -61.00  30.00  150
  9  ω   -135.00-109.00   0.50    1.03    -- -100.00-116.00  -8.00   52
 10  ω     50.00  75.00   0.50    0.05    --   44.85-116.00  -8.00   50
 11  ω     57.00  82.00   0.50    0.05    --   44.85-167.00-154.00   50
 12  ω     66.00  91.00   0.50    1.03    --  105.84-167.00-154.00   50
 13  ω     65.00 110.00   0.50    1.03    --  105.84-125.00-150.00   90
 14  ω     71.00 105.00   0.50    1.03    --  105.84-116.00  -8.00   68
 15  ω     45.00  72.00   0.50    1.03    --  105.84 -61.00  30.00   54
 16  ω     34.00  60.00   0.50    1.03    --  105.84 -77.00 150.00   52
 17  ω     71.00  98.00   0.50    1.03    --  105.84 -77.00 150.00   54
 18  ω     48.00  73.00   0.50    1.03    --  105.84 -61.00 -30.00   50
 19  ω     41.00  73.00   0.50    1.03    --  105.84 -61.00-120.00   64
 20  ω     88.00 134.00   0.50    1.03    --  105.84  45.00-120.00   92
 21  ω    152.00 177.00   0.50    1.03    --  105.84  45.00-120.00   50
 22  ω     94.00 119.00   0.50    0.05    --   44.85 167.00-133.00   50
 23  ω     78.00 103.00   0.50    1.03    --  105.84 167.00-133.00   50
 24  ω     86.00 154.00   0.50    1.03    --  105.84 116.00  80.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0174131000
_diffrn_orient_matrix_UB_12      0.1101992000
_diffrn_orient_matrix_UB_13      -0.0556511000
_diffrn_orient_matrix_UB_21      0.0249799000
_diffrn_orient_matrix_UB_22      0.0801209000
_diffrn_orient_matrix_UB_23      0.0768082000
_diffrn_orient_matrix_UB_31      0.1825993000
_diffrn_orient_matrix_UB_32      -0.0216511000
_diffrn_orient_matrix_UB_33      0.0012867000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2575
_reflns_number_total             2915
_reflns_odcompleteness_completeness 99.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.1090
_refine_ls_restrained_S_all      1.249
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1235P)²+4.8991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3220
_refine_ls_wR_factor_ref         0.3254
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C2(H2), C3(H3), C4(H4), C9(H9), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O15 O 0.2454(4) 0.7504(3) 0.7489(2) 0.0343(8) Uani 1 1 d . . . . .
O16 O 0.1070(4) 0.6813(3) 0.4618(2) 0.0366(9) Uani 1 1 d . . . . .
H16 H 0.051343 0.712836 0.422666 0.055 Uiso 1 1 calc R U . . .
O17 O 0.4543(5) 0.7030(4) 0.8290(2) 0.0407(9) Uani 1 1 d . . . . .
C7 C 0.2947(6) 0.6066(4) 0.6038(3) 0.0316(10) Uani 1 1 d . . . . .
C1 C 0.1632(6) 0.7785(4) 0.6736(3) 0.0317(10) Uani 1 1 d . . . . .
C19 C 0.5632(6) 0.9616(5) 0.6719(3) 0.0337(11) Uani 1 1 d . . . . .
H19 H 0.680060 0.952498 0.689012 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2410(6) 0.4985(5) 0.5679(3) 0.0338(11) Uani 1 1 d . . . . .
H8 H 0.132606 0.491278 0.546480 0.041 Uiso 1 1 calc R U . . .
C14 C 0.4049(6) 0.7287(4) 0.7591(3) 0.0330(11) Uani 1 1 d . . . . .
C2 C 0.0627(6) 0.8767(5) 0.6757(3) 0.0353(11) Uani 1 1 d . . . . .
H2 H 0.054229 0.920634 0.725133 0.042 Uiso 1 1 calc R U . . .
C6 C 0.1794(6) 0.7084(4) 0.6043(3) 0.0305(10) Uani 1 1 d . . . . .
C18 C 0.5037(6) 0.8439(4) 0.6315(3) 0.0320(10) Uani 1 1 d . . . . .
H18A H 0.567189 0.828940 0.583296 0.038 Uiso 1 1 calc R U . . .
H18B H 0.390555 0.855426 0.610505 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5122(6) 0.7288(4) 0.6864(3) 0.0328(11) Uani 1 1 d . . . . .
C3 C -0.0253(6) 0.9097(5) 0.6041(3) 0.0362(11) Uani 1 1 d . . . . .
H3 H -0.093235 0.978058 0.603832 0.043 Uiso 1 1 calc R U . . .
C4 C -0.0142(6) 0.8427(5) 0.5327(3) 0.0347(11) Uani 1 1 d . . . . .
H4 H -0.076603 0.864148 0.483910 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3452(7) 0.4018(5) 0.5634(3) 0.0369(11) Uani 1 1 d . . . . .
H9 H 0.307057 0.327910 0.540687 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4537(6) 0.6160(4) 0.6378(3) 0.0311(10) Uani 1 1 d . . . . .
C11 C 0.5565(6) 0.5191(4) 0.6294(3) 0.0331(11) Uani 1 1 d . . . . .
H11 H 0.665604 0.525605 0.649871 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0882(6) 0.7445(5) 0.5326(3) 0.0329(11) Uani 1 1 d . . . . .
C22 C 0.6853(6) 0.7158(5) 0.7231(3) 0.0373(11) Uani 1 1 d . . . . .
H22A H 0.713130 0.784832 0.758397 0.056 Uiso 1 1 calc R U . . .
H22B H 0.758532 0.711954 0.678596 0.056 Uiso 1 1 calc R U . . .
H22C H 0.695091 0.642133 0.755861 0.056 Uiso 1 1 calc R U . . .
C10 C 0.5038(7) 0.4134(5) 0.5919(3) 0.0364(11) Uani 1 1 d . . . . .
H10 H 0.576819 0.349110 0.585887 0.044 Uiso 1 1 calc R U . . .
C21 C 0.4757(7) 0.9954(5) 0.7473(3) 0.0415(12) Uani 1 1 d . . . . .
H21A H 0.359664 0.996887 0.732973 0.062 Uiso 1 1 calc R U . . .
H21B H 0.511247 1.074832 0.766586 0.062 Uiso 1 1 calc R U . . .
H21C H 0.499668 0.936355 0.790908 0.062 Uiso 1 1 calc R U . . .
C20 C 0.5451(7) 1.0617(5) 0.6078(4) 0.0459(14) Uani 1 1 d . . . . .
H20A H 0.605294 1.040812 0.560209 0.069 Uiso 1 1 calc R U . . .
H20B H 0.587157 1.136719 0.632021 0.069 Uiso 1 1 calc R U . . .
H20C H 0.431204 1.071829 0.590155 0.069 Uiso 1 1 calc R U . . .


_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
O15 C1 1.400(6) . ?
O15 C14 1.351(6) . ?
O16 H16 0.8400 . ?
O16 C5 1.371(6) . ?
O17 C14 1.219(6) . ?
C7 C8 1.401(7) . ?
C7 C6 1.489(7) . ?
C7 C12 1.406(7) . ?
C1 C2 1.381(7) . ?
C1 C6 1.388(7) . ?
C19 H19 1.0000 . ?
C19 C18 1.537(7) . ?
C19 C21 1.517(7) . ?
C19 C20 1.531(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(7) . ?
C14 C13 1.532(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(7) . ?
C6 C5 1.409(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C13 1.565(7) . ?
C13 C12 1.549(7) . ?
C13 C22 1.532(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(8) . ?
C12 C11 1.393(7) . ?
C11 H11 0.9500 . ?
C11 C10 1.387(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C10 H10 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C14 O15 C1 124.6(4) . . ?
C5 O16 H16 109.5 . . ?
C8 C7 C6 118.1(4) . . ?
C8 C7 C12 119.7(5) . . ?
C12 C7 C6 122.2(4) . . ?
C2 C1 O15 114.8(4) . . ?
C2 C1 C6 124.0(4) . . ?
C6 C1 O15 121.2(4) . . ?
C18 C19 H19 108.2 . . ?
C21 C19 H19 108.2 . . ?
C21 C19 C18 113.6(4) . . ?
C21 C19 C20 109.8(5) . . ?
C20 C19 H19 108.2 . . ?
C20 C19 C18 108.5(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(5) . . ?
C9 C8 H8 119.8 . . ?
O15 C14 C13 121.7(4) . . ?
O17 C14 O15 115.2(5) . . ?
O17 C14 C13 123.0(5) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(5) . . ?
C3 C2 H2 120.7 . . ?
C1 C6 C7 122.2(4) . . ?
C1 C6 C5 115.8(5) . . ?
C5 C6 C7 121.8(4) . . ?
C19 C18 H18A 108.0 . . ?
C19 C18 H18B 108.0 . . ?
C19 C18 C13 117.1(4) . . ?
H18A C18 H18B 107.3 . . ?
C13 C18 H18A 108.0 . . ?
C13 C18 H18B 108.0 . . ?
C14 C13 C18 115.9(4) . . ?
C14 C13 C12 102.4(4) . . ?
C14 C13 C22 106.4(4) . . ?
C12 C13 C18 112.0(4) . . ?
C22 C13 C18 107.8(4) . . ?
C22 C13 C12 112.2(4) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.9(5) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.9(5) . . ?
C10 C9 H9 120.1 . . ?
C7 C12 C13 121.2(4) . . ?
C11 C12 C7 118.3(4) . . ?
C11 C12 C13 120.5(4) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 C12 121.7(5) . . ?
C10 C11 H11 119.2 . . ?
O16 C5 C6 117.6(4) . . ?
O16 C5 C4 120.8(4) . . ?
C4 C5 C6 121.5(4) . . ?
C13 C22 H22A 109.5 . . ?
C13 C22 H22B 109.5 . . ?
C13 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C9 C10 C11 119.8(5) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O15 C1 C2 C3 -179.0(4) . . . . ?
O15 C1 C6 C7 -5.4(7) . . . . ?
O15 C1 C6 C5 178.8(4) . . . . ?
O15 C14 C13 C18 53.6(6) . . . . ?
O15 C14 C13 C12 -68.6(5) . . . . ?
O15 C14 C13 C22 173.5(4) . . . . ?
O17 C14 C13 C18 -130.4(5) . . . . ?
O17 C14 C13 C12 107.4(5) . . . . ?
O17 C14 C13 C22 -10.5(7) . . . . ?
C7 C8 C9 C10 -2.2(7) . . . . ?
C7 C6 C5 O16 1.1(7) . . . . ?
C7 C6 C5 C4 -177.2(5) . . . . ?
C7 C12 C11 C10 -2.9(7) . . . . ?
C1 O15 C14 O17 -178.4(4) . . . . ?
C1 O15 C14 C13 -2.1(7) . . . . ?
C1 C2 C3 C4 1.4(7) . . . . ?
C1 C6 C5 O16 176.8(4) . . . . ?
C1 C6 C5 C4 -1.5(7) . . . . ?
C19 C18 C13 C14 64.8(6) . . . . ?
C19 C18 C13 C12 -178.3(4) . . . . ?
C19 C18 C13 C22 -54.3(6) . . . . ?
C8 C7 C6 C1 135.0(5) . . . . ?
C8 C7 C6 C5 -49.5(6) . . . . ?
C8 C7 C12 C13 -173.2(4) . . . . ?
C8 C7 C12 C11 4.5(7) . . . . ?
C8 C9 C10 C11 3.8(7) . . . . ?
C14 O15 C1 C2 -131.5(5) . . . . ?
C14 O15 C1 C6 50.9(6) . . . . ?
C14 C13 C12 C7 62.1(5) . . . . ?
C14 C13 C12 C11 -115.5(5) . . . . ?
C2 C1 C6 C7 177.1(5) . . . . ?
C2 C1 C6 C5 1.4(7) . . . . ?
C2 C3 C4 C5 -1.6(8) . . . . ?
C6 C7 C8 C9 177.9(4) . . . . ?
C6 C7 C12 C13 6.9(7) . . . . ?
C6 C7 C12 C11 -175.5(4) . . . . ?
C6 C1 C2 C3 -1.4(8) . . . . ?
C18 C13 C12 C7 -62.7(6) . . . . ?
C18 C13 C12 C11 119.7(5) . . . . ?
C13 C12 C11 C10 174.8(4) . . . . ?
C3 C4 C5 O16 -176.6(5) . . . . ?
C3 C4 C5 C6 1.6(7) . . . . ?
C12 C7 C8 C9 -2.0(7) . . . . ?
C12 C7 C6 C1 -45.1(7) . . . . ?
C12 C7 C6 C5 130.4(5) . . . . ?
C12 C11 C10 C9 -1.3(7) . . . . ?
C22 C13 C12 C7 175.8(4) . . . . ?
C22 C13 C12 C11 -1.8(6) . . . . ?
C21 C19 C18 C13 -57.8(6) . . . . ?
C20 C19 C18 C13 179.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.235
_oxdiff_exptl_absorpt_empirical_full_min 0.533
####################################################################### 
# 
# 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_zhangyu_181205
_database_code_depnum_ccdc_archive 'CCDC 2334678'
loop_
_audit_author_name
_audit_author_address
zhangyu
;Sun Yat sen University
China
;
_audit_update_record             
;
2024-02-22 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_audit_creation_date             2018-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O3'
_chemical_formula_sum            'C18 H18 O3'
_chemical_formula_weight         282.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.96310(10)
_cell_length_b                   9.04150(10)
_cell_length_c                   19.89230(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1432.21(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13476
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.8420
_cell_measurement_theta_min      4.4300
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.815
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14434
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.008
_diffrn_reflns_theta_min         4.445
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  61.00   0.50    0.05    --   46.62 -49.00 -47.00  172
  2  ω   -173.00 -76.00   0.50    0.05    -- -100.00 -77.00 114.00  194
  3  ω     85.00 178.00   0.50    0.05    --  107.00 106.00 -34.00  186
  4  ω     34.00 122.00   0.50    0.05    --  107.00 -49.00 -47.00  176
  5  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00  30.00   96
  6  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00 -30.00   96
  7  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00  60.00   96
  8  ω     15.00  95.00   0.50    0.05    --   46.62-125.00-180.00  160
  9  ω   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00 150.00  174
 10  ω   -117.00 -27.00   0.50    0.05    -- -100.00 125.00  90.00  180
 11  ω     89.00 178.00   0.50    0.05    --  107.00  15.00 -90.00  178
 12  ω     89.00 178.00   0.50    0.05    --  107.00  15.00-150.00  178
 13  ω     34.00 131.00   0.50    0.05    --  107.00 -77.00 -30.00  194
 14  ω     34.00 125.00   0.50    0.05    --  107.00 -61.00-180.00  182
 15  ω     34.00 108.00   0.50    0.05    --  107.00 -95.00  90.00  148
 16  ω     32.00 120.00   0.50    0.05    --   46.62  49.00 100.00  176
 17  ω     23.00 120.00   0.50    0.05    --   46.62  77.00   0.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0210150000
_diffrn_orient_matrix_UB_12      0.0907633000
_diffrn_orient_matrix_UB_13      -0.0650020000
_diffrn_orient_matrix_UB_21      0.1861652000
_diffrn_orient_matrix_UB_22      0.0457575000
_diffrn_orient_matrix_UB_23      0.0035410000
_diffrn_orient_matrix_UB_31      0.0483185000
_diffrn_orient_matrix_UB_32      -0.1367480000
_diffrn_orient_matrix_UB_33      -0.0419422000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                2898
_reflns_number_total             2939
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.2541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0745
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00H(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00F(H00G), C00G(H00H), C00I(H00K), C00J(H00L),
 C00K(H00M)
2.c Idealised Me refined as rotating group:
 C00D(H00D,H00E,H00F), C00L(H00N,H00O,H00P)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.29344(13) 0.34914(11) 0.55640(5) 0.0158(2) Uani 1 1 d . . . . .
O002 O 0.28947(15) 0.12615(12) 0.59675(6) 0.0200(2) Uani 1 1 d . . . . .
O003 O 0.31817(16) 0.84124(12) 0.64862(6) 0.0218(3) Uani 1 1 d . . . . .
H003 H 0.328462 0.926025 0.634577 0.033 Uiso 1 1 calc GR . . . .
C004 C 0.29827(18) 0.40951(15) 0.70430(7) 0.0136(3) Uani 1 1 d . . . . .
C005 C 0.34004(18) 0.49797(16) 0.55474(8) 0.0151(3) Uani 1 1 d . . . . .
C006 C 0.3475(2) 0.74372(16) 0.59756(8) 0.0169(3) Uani 1 1 d . . . . .
C007 C 0.33412(19) 0.25239(16) 0.60578(7) 0.0141(3) Uani 1 1 d . . . . .
C008 C 0.23886(18) 0.54003(17) 0.67352(7) 0.0136(3) Uani 1 1 d . . . . .
C009 C 0.11582(19) 0.62399(17) 0.70616(8) 0.0173(3) Uani 1 1 d . . . . .
H009 H 0.073881 0.708110 0.685135 0.021 Uiso 1 1 calc R . . . .
C00A C 0.59587(18) 0.38290(16) 0.65329(7) 0.0153(3) Uani 1 1 d . . . . .
H00A H 0.574398 0.484536 0.640262 0.018 Uiso 1 1 calc R . . . .
H00B H 0.662820 0.384947 0.694020 0.018 Uiso 1 1 calc R . . . .
C00B C 0.42485(18) 0.30661(16) 0.66917(7) 0.0140(3) Uani 1 1 d . . . . .
C00C C 0.2360(2) 0.37322(17) 0.76815(8) 0.0171(3) Uani 1 1 d . . . . .
H00C H 0.275039 0.288289 0.789386 0.021 Uiso 1 1 calc R . . . .
C00D C 0.4637(2) 0.16920(17) 0.71153(8) 0.0179(3) Uani 1 1 d . . . . .
H00D H 0.515857 0.198726 0.752917 0.027 Uiso 1 1 calc GR . . . .
H00E H 0.538288 0.105433 0.687099 0.027 Uiso 1 1 calc GR . . . .
H00F H 0.361220 0.117372 0.721114 0.027 Uiso 1 1 calc GR . . . .
C00E C 0.30610(19) 0.59350(16) 0.60818(7) 0.0147(3) Uani 1 1 d . . . . .
C00F C 0.0549(2) 0.58525(18) 0.76884(8) 0.0203(3) Uani 1 1 d . . . . .
H00G H -0.027381 0.642301 0.789540 0.024 Uiso 1 1 calc R . . . .
C00G C 0.4201(2) 0.79128(18) 0.53759(8) 0.0207(3) Uani 1 1 d . . . . .
H00H H 0.447674 0.890431 0.531852 0.025 Uiso 1 1 calc R . . . .
C00H C 0.6982(2) 0.30804(17) 0.59768(8) 0.0196(3) Uani 1 1 d . . . . .
H00I H 0.711837 0.204000 0.608240 0.024 Uiso 1 1 calc R . . . .
H00J H 0.637811 0.315346 0.555457 0.024 Uiso 1 1 calc R . . . .
C00I C 0.1179(2) 0.46032(18) 0.80045(8) 0.0200(3) Uani 1 1 d . . . . .
H00K H 0.080975 0.435096 0.843288 0.024 Uiso 1 1 calc R . . . .
C00J C 0.4106(2) 0.54320(19) 0.49456(8) 0.0209(3) Uani 1 1 d . . . . .
H00L H 0.430395 0.475644 0.460206 0.025 Uiso 1 1 calc R . . . .
C00K C 0.4510(2) 0.69084(19) 0.48658(8) 0.0231(4) Uani 1 1 d . . . . .
H00M H 0.499447 0.722924 0.446608 0.028 Uiso 1 1 calc R . . . .
C00L C 0.8702(2) 0.3795(2) 0.59016(9) 0.0245(4) Uani 1 1 d . . . . .
H00N H 0.930982 0.331337 0.554699 0.037 Uiso 1 1 calc GR . . . .
H00O H 0.931305 0.369872 0.631536 0.037 Uiso 1 1 calc GR . . . .
H00P H 0.856853 0.482400 0.579512 0.037 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C005 1.3963(17) . ?
O001 C007 1.3546(18) . ?
O002 C007 1.2090(19) . ?
O003 H003 0.8200 . ?
O003 C006 1.3651(18) . ?
C004 C008 1.411(2) . ?
C004 C00B 1.539(2) . ?
C004 C00C 1.403(2) . ?
C005 C00E 1.396(2) . ?
C005 C00J 1.384(2) . ?
C006 C00E 1.414(2) . ?
C006 C00G 1.393(2) . ?
C007 C00B 1.534(2) . ?
C008 C009 1.399(2) . ?
C008 C00E 1.486(2) . ?
C009 H009 0.9300 . ?
C009 C00F 1.383(2) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00B 1.559(2) . ?
C00A C00H 1.531(2) . ?
C00B C00D 1.533(2) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.384(2) . ?
C00D H00D 0.9600 . ?
C00D H00E 0.9600 . ?
C00D H00F 0.9600 . ?
C00F H00G 0.9300 . ?
C00F C00I 1.387(2) . ?
C00G H00H 0.9300 . ?
C00G C00K 1.384(2) . ?
C00H H00I 0.9700 . ?
C00H H00J 0.9700 . ?
C00H C00L 1.522(2) . ?
C00I H00K 0.9300 . ?
C00J H00L 0.9300 . ?
C00J C00K 1.382(2) . ?
C00K H00M 0.9300 . ?
C00L H00N 0.9600 . ?
C00L H00O 0.9600 . ?
C00L H00P 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 O001 C005 125.17(12) . . ?
C006 O003 H003 109.5 . . ?
C008 C004 C00B 121.87(13) . . ?
C00C C004 C008 118.04(14) . . ?
C00C C004 C00B 120.08(13) . . ?
O001 C005 C00E 121.78(13) . . ?
C00J C005 O001 114.40(13) . . ?
C00J C005 C00E 123.67(14) . . ?
O003 C006 C00E 118.00(13) . . ?
O003 C006 C00G 120.57(14) . . ?
C00G C006 C00E 121.41(14) . . ?
O001 C007 C00B 120.16(12) . . ?
O002 C007 O001 115.57(13) . . ?
O002 C007 C00B 124.23(13) . . ?
C004 C008 C00E 122.05(13) . . ?
C009 C008 C004 119.15(13) . . ?
C009 C008 C00E 118.78(14) . . ?
C008 C009 H009 119.1 . . ?
C00F C009 C008 121.78(15) . . ?
C00F C009 H009 119.1 . . ?
H00A C00A H00B 107.6 . . ?
C00B C00A H00A 108.6 . . ?
C00B C00A H00B 108.6 . . ?
C00H C00A H00A 108.6 . . ?
C00H C00A H00B 108.6 . . ?
C00H C00A C00B 114.55(12) . . ?
C004 C00B C00A 113.36(11) . . ?
C007 C00B C004 104.94(12) . . ?
C007 C00B C00A 112.73(12) . . ?
C00D C00B C004 111.87(12) . . ?
C00D C00B C007 106.73(12) . . ?
C00D C00B C00A 107.09(12) . . ?
C004 C00C H00C 119.1 . . ?
C00I C00C C004 121.83(15) . . ?
C00I C00C H00C 119.1 . . ?
C00B C00D H00D 109.5 . . ?
C00B C00D H00E 109.5 . . ?
C00B C00D H00F 109.5 . . ?
H00D C00D H00E 109.5 . . ?
H00D C00D H00F 109.5 . . ?
H00E C00D H00F 109.5 . . ?
C005 C00E C006 115.81(14) . . ?
C005 C00E C008 122.30(13) . . ?
C006 C00E C008 121.82(13) . . ?
C009 C00F H00G 120.4 . . ?
C009 C00F C00I 119.21(15) . . ?
C00I C00F H00G 120.4 . . ?
C006 C00G H00H 120.0 . . ?
C00K C00G C006 119.94(15) . . ?
C00K C00G H00H 120.0 . . ?
C00A C00H H00I 109.4 . . ?
C00A C00H H00J 109.4 . . ?
H00I C00H H00J 108.0 . . ?
C00L C00H C00A 111.23(13) . . ?
C00L C00H H00I 109.4 . . ?
C00L C00H H00J 109.4 . . ?
C00C C00I C00F 119.91(14) . . ?
C00C C00I H00K 120.0 . . ?
C00F C00I H00K 120.0 . . ?
C005 C00J H00L 120.7 . . ?
C00K C00J C005 118.63(15) . . ?
C00K C00J H00L 120.7 . . ?
C00G C00K H00M 119.7 . . ?
C00J C00K C00G 120.53(15) . . ?
C00J C00K H00M 119.7 . . ?
C00H C00L H00N 109.5 . . ?
C00H C00L H00O 109.5 . . ?
C00H C00L H00P 109.5 . . ?
H00N C00L H00O 109.5 . . ?
H00N C00L H00P 109.5 . . ?
H00O C00L H00P 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
O001 C005 C00E C006 -174.92(13) . . . . ?
O001 C005 C00E C008 8.1(2) . . . . ?
O001 C005 C00J C00K 175.98(15) . . . . ?
O001 C007 C00B C004 65.43(16) . . . . ?
O001 C007 C00B C00A -58.40(17) . . . . ?
O001 C007 C00B C00D -175.69(13) . . . . ?
O002 C007 C00B C004 -112.10(16) . . . . ?
O002 C007 C00B C00A 124.07(16) . . . . ?
O002 C007 C00B C00D 6.8(2) . . . . ?
O003 C006 C00E C005 -179.38(13) . . . . ?
O003 C006 C00E C008 -2.4(2) . . . . ?
O003 C006 C00G C00K 179.20(16) . . . . ?
C004 C008 C009 C00F 2.2(2) . . . . ?
C004 C008 C00E C005 41.7(2) . . . . ?
C004 C008 C00E C006 -135.12(15) . . . . ?
C004 C00C C00I C00F 1.7(2) . . . . ?
C005 O001 C007 O002 -176.42(13) . . . . ?
C005 O001 C007 C00B 5.8(2) . . . . ?
C005 C00J C00K C00G -0.6(3) . . . . ?
C006 C00G C00K C00J 0.0(3) . . . . ?
C007 O001 C005 C00E -53.9(2) . . . . ?
C007 O001 C005 C00J 130.44(15) . . . . ?
C008 C004 C00B C007 -62.13(16) . . . . ?
C008 C004 C00B C00A 61.29(17) . . . . ?
C008 C004 C00B C00D -177.49(13) . . . . ?
C008 C004 C00C C00I 0.9(2) . . . . ?
C008 C009 C00F C00I 0.4(2) . . . . ?
C009 C008 C00E C005 -139.97(16) . . . . ?
C009 C008 C00E C006 43.3(2) . . . . ?
C009 C00F C00I C00C -2.3(2) . . . . ?
C00B C004 C008 C009 175.93(13) . . . . ?
C00B C004 C008 C00E -5.7(2) . . . . ?
C00B C004 C00C C00I -177.87(14) . . . . ?
C00B C00A C00H C00L -174.24(13) . . . . ?
C00C C004 C008 C009 -2.8(2) . . . . ?
C00C C004 C008 C00E 175.58(14) . . . . ?
C00C C004 C00B C007 116.57(14) . . . . ?
C00C C004 C00B C00A -120.00(15) . . . . ?
C00C C004 C00B C00D 1.21(19) . . . . ?
C00E C005 C00J C00K 0.4(2) . . . . ?
C00E C006 C00G C00K 0.8(3) . . . . ?
C00E C008 C009 C00F -176.20(14) . . . . ?
C00G C006 C00E C005 -1.0(2) . . . . ?
C00G C006 C00E C008 176.01(14) . . . . ?
C00H C00A C00B C004 -158.79(13) . . . . ?
C00H C00A C00B C007 -39.74(17) . . . . ?
C00H C00A C00B C00D 77.34(15) . . . . ?
C00J C005 C00E C006 0.4(2) . . . . ?
C00J C005 C00E C008 -176.58(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.731
