# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

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

data_exp_762_abs_nofix
_database_code_depnum_ccdc_archive 'CCDC 1881470'
_audit_update_record             
;
2019-01-22 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H10 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8179(5)
_cell_length_b                   4.53024(16)
_cell_length_c                   16.5413(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.096(3)
_cell_angle_gamma                90
_cell_volume                     1035.46(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9522
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.4810
_cell_measurement_theta_min      2.4410
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over 			a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 1 1 0.2575
-4 5 -2 0.2226
-1 0 0 0.2731
-1 0 -1 0.2204
0 -1 0 0.2703
0 0 1 0.0181
0 0 -1 0.0281
1 0 0 0.2462
1 -1 0 0.2757
1 0 1 0.1738
2 2 -1 0.3315
5 -1 -1 0.2523

_exptl_crystal_size_max          0.644
_exptl_crystal_size_mid          0.503
_exptl_crystal_size_min          0.046
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.0000 1.0000 1.0000 0.0181 0.3003 -0.0417
-4.0000 5.0000 -2.0000 0.1676 0.6295 0.4879
-1.0000 0.0000 0.0000 0.0103 0.0388 -0.0320
-1.0000 0.0000 -1.0000 0.0523 0.0307 -0.0284
-0.0000 -1.0000 0.0000 -0.0085 -0.0981 -0.1217
0.0000 0.0000 1.0000 -0.0420 0.0081 -0.0036
-0.0000 -0.0000 -1.0000 0.0420 -0.0081 0.0036
1.0000 -0.0000 -0.0000 -0.0103 -0.0388 0.0320
1.0000 -1.0000 -0.0000 -0.0188 -0.1369 -0.0898
1.0000 -0.0000 1.0000 -0.0523 -0.0307 0.0284
2.0000 2.0000 -1.0000 0.0383 0.1104 0.3110
5.0000 -1.0000 -1.0000 -0.0181 -0.3003 0.0417

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25336
_diffrn_reflns_point_group_measured_fraction_full 1.001
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.496
_diffrn_reflns_theta_min         2.463
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0026
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  97.00   1.00   20.00    --   27.00  77.00 -90.00  100
  2  ω     21.00 103.00   1.00   20.00    --   27.00-160.00  60.00   82
  3  ω    -20.00  69.00   1.00   20.00    --   27.00 -99.00 150.00   89
  4  ω     -3.00  97.00   1.00   20.00    --   27.00  77.00  60.00  100
  5  ω    -96.00  -6.00   1.00   20.00    --  -27.15 -57.00 -60.00   90
  6  ω   -100.00  46.00   1.00   20.00    --  -27.15   0.00 -60.00  146
  7  ω      6.00  96.00   1.00   20.00    --   27.00  57.00-180.00   90
  8  ω      6.00  96.00   1.00   20.00    --   27.00  57.00-120.00   90
  9  ω    -99.00 -49.00   1.00   20.00    --  -27.15-160.00 150.00   50
 10  ω    -57.00  43.00   1.00   20.00    --  -27.15  77.00 -90.00  100
 11  ω    -99.00 -49.00   1.00   20.00    --  -27.15-160.00 -60.00   50
 12  ω    -42.00  -5.00   1.00   20.00    --   27.00 -57.00  30.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0103138861
_diffrn_orient_matrix_UB_12      0.0084841370
_diffrn_orient_matrix_UB_13      -0.0419535368
_diffrn_orient_matrix_UB_21      -0.0388147421
_diffrn_orient_matrix_UB_22      0.0980919360
_diffrn_orient_matrix_UB_23      0.0081239996
_diffrn_orient_matrix_UB_31      0.0319691932
_diffrn_orient_matrix_UB_32      0.1217383131
_diffrn_orient_matrix_UB_33      -0.0035557623
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    1.002
_reflns_Friedel_fraction_max     1.001
_reflns_number_gt                6125
_reflns_number_total             6345
_reflns_odcompleteness_completeness 89.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.95
_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 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (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    ?
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.483(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         6345
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0628
_refine_ls_restrained_S_all      1.096
_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)+(0.0954P)²+0.7770P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1776
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.517(3)
 0.483(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C2(H2), C10(H10), C7(H7), C4(H4), C6(H6), C9(H9), C8(H8),
 C22(H22), C24(H24), C26(H26), C23(H23), C21(H21), C25(H25), C18(H18), C20(H20),
  C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C15 C 0.7781(3) 0.6607(10) 0.5964(2) 0.0140(7) Uani 1 1 d . . . . .
C16 C 0.7620(3) 0.4624(11) 0.6617(3) 0.0176(8) Uani 1 1 d . . . . .
C14 C 0.6700(4) 0.3237(10) 0.6714(3) 0.0201(9) Uani 1 1 d . . . . .
C11 C 0.7005(3) 0.7280(10) 0.5427(2) 0.0152(7) Uani 1 1 d . . . . .
C1 C 0.7184(3) 0.9277(10) 0.4801(3) 0.0169(8) Uani 1 1 d . . . . .
C3 C 0.8834(3) 0.9950(11) 0.5218(3) 0.0212(9) Uani 1 1 d . . . . .
H3 H 0.9447 1.0858 0.5143 0.025 Uiso 1 1 calc R . . . .
C12 C 0.8703(3) 0.7949(10) 0.5857(3) 0.0165(8) Uani 1 1 d . . . . .
C5 C 0.9319(4) 0.5373(12) 0.7040(3) 0.0262(11) Uani 1 1 d . . . . .
H5 H 0.9837 0.4998 0.7405 0.031 Uiso 1 1 calc R . . . .
C2 C 0.8082(3) 1.0613(11) 0.4699(3) 0.0202(9) Uani 1 1 d . . . . .
H2 H 0.8178 1.1983 0.4272 0.024 Uiso 1 1 calc R . . . .
C10 C 0.6078(3) 0.5902(12) 0.5541(3) 0.0216(9) Uani 1 1 d . . . . .
H10 H 0.5558 0.6319 0.5182 0.026 Uiso 1 1 calc R . . . .
C13 C 0.8396(4) 0.3941(11) 0.7164(3) 0.0238(10) Uani 1 1 d . . . . .
C7 C 0.7340(5) 0.0628(13) 0.7884(3) 0.0356(14) Uani 1 1 d . . . . .
H7 H 0.7248 -0.0767 0.8306 0.043 Uiso 1 1 calc R . . . .
C4 C 0.9453(3) 0.7209(12) 0.6422(3) 0.0226(9) Uani 1 1 d . . . . .
H4 H 1.0074 0.8070 0.6352 0.027 Uiso 1 1 calc R . . . .
C6 C 0.8219(5) 0.1950(13) 0.7806(3) 0.0345(13) Uani 1 1 d . . . . .
H6 H 0.8717 0.1535 0.8186 0.041 Uiso 1 1 calc R . . . .
C9 C 0.5949(3) 0.3971(10) 0.6175(3) 0.0209(9) Uani 1 1 d . . . . .
H9 H 0.5330 0.3102 0.6251 0.025 Uiso 1 1 calc R . . . .
C8 C 0.6572(5) 0.1254(11) 0.7365(3) 0.0310(12) Uani 1 1 d . . . . .
H8 H 0.5960 0.0346 0.7449 0.037 Uiso 1 1 calc R . . . .
C32 C 0.2743(3) 0.4306(9) 0.9021(2) 0.0132(7) Uani 1 1 d . . . . .
C31 C 0.2515(3) 0.6387(10) 0.8402(2) 0.0143(7) Uani 1 1 d . . . . .
C28 C 0.1572(3) 0.7606(10) 0.8338(3) 0.0184(8) Uani 1 1 d . . . . .
C29 C 0.2015(4) 0.3451(11) 0.9591(3) 0.0198(8) Uani 1 1 d . . . . .
C22 C 0.2228(4) 0.1433(12) 1.0202(3) 0.0247(10) Uani 1 1 d . . . . .
H22 H 0.1741 0.0846 1.0574 0.030 Uiso 1 1 calc R . . . .
C30 C 0.3681(3) 0.3074(10) 0.9083(3) 0.0176(8) Uani 1 1 d . . . . .
C24 C 0.3868(4) 0.1005(12) 0.9716(3) 0.0230(9) Uani 1 1 d . . . . .
H24 H 0.4490 0.0123 0.9758 0.028 Uiso 1 1 calc R . . . .
C26 C 0.4189(3) 0.5890(10) 0.7903(3) 0.0178(8) Uani 1 1 d . . . . .
H26 H 0.4681 0.6436 0.7532 0.021 Uiso 1 1 calc R . . . .
C23 C 0.3166(4) 0.0275(11) 1.0264(3) 0.0256(10) Uani 1 1 d . . . . .
H23 H 0.3317 -0.1040 1.0693 0.031 Uiso 1 1 calc R . . . .
C27 C 0.3244(3) 0.7142(9) 0.7825(2) 0.0134(7) Uani 1 1 d . . . . .
C21 C 0.1054(4) 0.4750(13) 0.9498(3) 0.0239(9) Uani 1 1 d . . . . .
H21 H 0.0558 0.4177 0.9862 0.029 Uiso 1 1 calc R . . . .
C25 C 0.4395(3) 0.3898(11) 0.8511(3) 0.0218(9) Uani 1 1 d . . . . .
H25 H 0.5024 0.3067 0.8547 0.026 Uiso 1 1 calc R . . . .
C18 C 0.2083(3) 1.0453(11) 0.7175(3) 0.0209(9) Uani 1 1 d . . . . .
H18 H 0.1938 1.1849 0.6764 0.025 Uiso 1 1 calc R . . . .
C20 C 0.0844(3) 0.6716(12) 0.8919(3) 0.0245(10) Uani 1 1 d . . . . .
H20 H 0.0212 0.7535 0.8888 0.029 Uiso 1 1 calc R . . . .
C17 C 0.3004(3) 0.9178(10) 0.7220(2) 0.0181(8) Uani 1 1 d . . . . .
C19 C 0.1382(3) 0.9664(12) 0.7736(3) 0.0214(8) Uani 1 1 d . . . . .
H19 H 0.0759 1.0550 0.7707 0.026 Uiso 1 1 calc R . . . .
O1 O 0.6417(3) 0.9719(9) 0.42695(19) 0.0239(6) Uani 1 1 d . . . . .
O2 O 0.3696(3) 0.9722(9) 0.66448(19) 0.0250(6) Uani 1 1 d . . . . .
H2A H 0.370(5) 1.121(16) 0.623(4) 0.037 Uiso 1 1 d R . . . .
H1 H 0.651(5) 1.150(18) 0.414(4) 0.037 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C15 C16 1.423(6) . ?
C15 C11 1.425(5) . ?
C15 C12 1.424(6) . ?
C16 C14 1.427(6) . ?
C16 C13 1.435(6) . ?
C14 C9 1.407(7) . ?
C14 C8 1.414(7) . ?
C11 C1 1.398(6) . ?
C11 C10 1.437(6) . ?
C1 C2 1.391(6) . ?
C1 O1 1.391(5) . ?
C3 C12 1.404(7) . ?
C3 C2 1.380(7) . ?
C12 C4 1.435(6) . ?
C5 C13 1.446(7) . ?
C5 C4 1.331(8) . ?
C10 C9 1.377(7) . ?
C13 C6 1.416(8) . ?
C7 C6 1.360(10) . ?
C7 C8 1.393(9) . ?
C32 C31 1.426(6) . ?
C32 C29 1.434(6) . ?
C32 C30 1.414(6) . ?
C31 C28 1.419(6) . ?
C31 C27 1.430(5) . ?
C28 C20 1.448(6) . ?
C28 C19 1.390(7) . ?
C29 C22 1.393(7) . ?
C29 C21 1.460(7) . ?
C22 C23 1.401(8) . ?
C30 C24 1.429(7) . ?
C30 C25 1.418(6) . ?
C24 C23 1.370(7) . ?
C26 C27 1.429(6) . ?
C26 C25 1.380(7) . ?
C27 C17 1.401(6) . ?
C21 C20 1.339(8) . ?
C18 C17 1.400(6) . ?
C18 C19 1.389(7) . ?
C17 O2 1.372(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 C15 C11 119.3(4) . . ?
C16 C15 C12 120.4(4) . . ?
C12 C15 C11 120.3(4) . . ?
C15 C16 C14 120.3(4) . . ?
C15 C16 C13 119.8(4) . . ?
C14 C16 C13 120.0(4) . . ?
C9 C14 C16 118.7(4) . . ?
C9 C14 C8 122.7(5) . . ?
C8 C14 C16 118.5(5) . . ?
C15 C11 C10 119.7(4) . . ?
C1 C11 C15 117.8(4) . . ?
C1 C11 C10 122.5(4) . . ?
C2 C1 C11 122.0(4) . . ?
O1 C1 C11 115.2(4) . . ?
O1 C1 C2 122.7(4) . . ?
C2 C3 C12 120.7(4) . . ?
C15 C12 C4 117.7(4) . . ?
C3 C12 C15 119.1(4) . . ?
C3 C12 C4 123.2(4) . . ?
C4 C5 C13 120.8(4) . . ?
C3 C2 C1 120.1(4) . . ?
C9 C10 C11 119.4(4) . . ?
C16 C13 C5 118.3(4) . . ?
C6 C13 C16 118.7(5) . . ?
C6 C13 C5 123.1(5) . . ?
C6 C7 C8 122.1(5) . . ?
C5 C4 C12 123.1(4) . . ?
C7 C6 C13 120.5(5) . . ?
C10 C9 C14 122.5(4) . . ?
C7 C8 C14 120.2(5) . . ?
C31 C32 C29 119.8(4) . . ?
C30 C32 C31 121.0(4) . . ?
C30 C32 C29 119.3(4) . . ?
C32 C31 C27 118.8(4) . . ?
C28 C31 C32 120.8(4) . . ?
C28 C31 C27 120.3(4) . . ?
C31 C28 C20 118.7(4) . . ?
C19 C28 C31 119.2(4) . . ?
C19 C28 C20 122.1(4) . . ?
C32 C29 C21 117.4(4) . . ?
C22 C29 C32 120.5(4) . . ?
C22 C29 C21 122.1(4) . . ?
C29 C22 C23 119.5(4) . . ?
C32 C30 C24 118.5(4) . . ?
C32 C30 C25 119.0(4) . . ?
C25 C30 C24 122.4(4) . . ?
C23 C24 C30 121.0(5) . . ?
C25 C26 C27 120.8(4) . . ?
C24 C23 C22 121.2(4) . . ?
C26 C27 C31 119.2(4) . . ?
C17 C27 C31 118.0(4) . . ?
C17 C27 C26 122.8(4) . . ?
C20 C21 C29 122.7(4) . . ?
C26 C25 C30 121.0(4) . . ?
C19 C18 C17 119.6(4) . . ?
C21 C20 C28 120.6(4) . . ?
C18 C17 C27 121.5(4) . . ?
O2 C17 C27 116.7(4) . . ?
O2 C17 C18 121.6(4) . . ?
C18 C19 C28 121.3(4) . . ?

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
O2 H2A O1 0.96(7) 1.80(7) 2.727(5) 161(6) 2_656
O1 H1 O2 0.84(8) 1.98(8) 2.729(5) 148(7) 2_656

_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 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.798
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.517(3)
2 0.483(3)

# start Validation Reply Form
_vrf_STRVA01_exp_762_abs_nofix   
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: The Flack parameter value of 0.48 agrees exactly
with the refined fraction of the pseudo-merohedral twin component,
and can be considered as a result of twinning.
;
_vrf_PLAT340_exp_762_abs_nofix   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00661 Ang.  
RESPONSE: This is most probably the result of two very similar
molecules being refined independently.
;
_vrf_PLAT911_exp_762_abs_nofix   
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: The reflections were occluded by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_t190
_database_code_depnum_ccdc_archive 'CCDC 1892299'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7983(5)
_cell_length_b                   4.54885(13)
_cell_length_c                   16.5972(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.979(3)
_cell_angle_gamma                90
_cell_volume                     1041.74(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3876
_cell_measurement_temperature    190.03(10)
_cell_measurement_theta_max      74.8620
_cell_measurement_theta_min      2.6640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6178
_diffrn_reflns_point_group_measured_fraction_full 0.848
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         2.662
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      190.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1013822000
_diffrn_orient_matrix_UB_12      -0.1407401000
_diffrn_orient_matrix_UB_13      0.0043667000
_diffrn_orient_matrix_UB_21      0.0010683000
_diffrn_orient_matrix_UB_22      -0.0319178000
_diffrn_orient_matrix_UB_23      -0.0924468000
_diffrn_orient_matrix_UB_31      0.0466933000
_diffrn_orient_matrix_UB_32      0.3063160000
_diffrn_orient_matrix_UB_33      -0.0075695000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.515
_reflns_Friedel_fraction_full    0.667
_reflns_Friedel_fraction_max     0.678
_reflns_number_gt                2903
_reflns_number_total             3017
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.545(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.013
_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)+(0.0997P)²+0.0841P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1335
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.455(3)
 0.545(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6414(2) 0.7263(9) 0.42724(18) 0.0359(7) Uani 1 1 d D . . . .
C1 C 0.7178(3) 0.6844(11) 0.4808(3) 0.0279(10) Uani 1 1 d . . . . .
C2 C 0.7013(3) 0.4878(11) 0.5434(3) 0.0258(9) Uani 1 1 d . . . . .
C3 C 0.6082(3) 0.3475(12) 0.5549(3) 0.0298(11) Uani 1 1 d . . . . .
H3 H 0.5573 0.3876 0.5199 0.036 Uiso 1 1 calc R . . . .
C4 C 0.5953(3) 0.1565(12) 0.6171(3) 0.0338(11) Uani 1 1 d . . . . .
H4 H 0.5349 0.0699 0.6242 0.041 Uiso 1 1 calc R . . . .
C5 C 0.6714(4) 0.0848(11) 0.6717(3) 0.0316(10) Uani 1 1 d . . . . .
C6 C 0.6597(4) -0.1114(14) 0.7363(3) 0.0432(12) Uani 1 1 d . . . . .
H6 H 0.6004 -0.2044 0.7441 0.052 Uiso 1 1 calc R . . . .
C7 C 0.7355(5) -0.1678(16) 0.7886(3) 0.0516(16) Uani 1 1 d . . . . .
H7 H 0.7265 -0.2999 0.8307 0.062 Uiso 1 1 calc R . . . .
C8 C 0.8240(5) -0.0327(15) 0.7796(3) 0.0499(15) Uani 1 1 d . . . . .
H8 H 0.8731 -0.0706 0.8165 0.060 Uiso 1 1 calc R . . . .
C9 C 0.8410(4) 0.1589(13) 0.7164(3) 0.0381(12) Uani 1 1 d . . . . .
C10 C 0.9316(4) 0.3010(14) 0.7028(3) 0.0402(13) Uani 1 1 d . . . . .
H10 H 0.9827 0.2618 0.7378 0.048 Uiso 1 1 calc R . . . .
C11 C 0.9464(4) 0.4889(14) 0.6418(3) 0.0396(12) Uani 1 1 d . . . . .
H11 H 1.0069 0.5760 0.6355 0.048 Uiso 1 1 calc R . . . .
C12 C 0.8702(3) 0.5577(12) 0.5858(3) 0.0302(10) Uani 1 1 d . . . . .
C13 C 0.8825(3) 0.7574(12) 0.5227(3) 0.0339(11) Uani 1 1 d . . . . .
H13 H 0.9419 0.8505 0.5158 0.041 Uiso 1 1 calc R . . . .
C14 C 0.8073(3) 0.8182(12) 0.4703(3) 0.0338(11) Uani 1 1 d . . . . .
H14 H 0.8167 0.9490 0.4279 0.041 Uiso 1 1 calc R . . . .
C15 C 0.7785(3) 0.4222(11) 0.5969(2) 0.0247(9) Uani 1 1 d . . . . .
C16 C 0.7627(3) 0.2251(13) 0.6618(3) 0.0295(10) Uani 1 1 d . . . . .
O2 O 0.3696(3) 0.7289(9) 0.66468(19) 0.0375(7) Uani 1 1 d D . . . .
C21 C 0.3003(3) 0.6763(11) 0.7226(3) 0.0286(10) Uani 1 1 d . . . . .
C22 C 0.3240(3) 0.4735(10) 0.7831(3) 0.0262(10) Uani 1 1 d . . . . .
C23 C 0.4189(3) 0.3462(12) 0.7904(3) 0.0312(11) Uani 1 1 d . . . . .
H23 H 0.4670 0.3952 0.7536 0.037 Uiso 1 1 calc R . . . .
C24 C 0.4385(3) 0.1543(12) 0.8510(3) 0.0361(12) Uani 1 1 d . . . . .
H24 H 0.5005 0.0755 0.8550 0.043 Uiso 1 1 calc R . . . .
C25 C 0.3678(4) 0.0704(12) 0.9083(3) 0.0321(10) Uani 1 1 d . . . . .
C26 C 0.3867(4) -0.1301(14) 0.9715(3) 0.0400(12) Uani 1 1 d . . . . .
H26 H 0.4481 -0.2125 0.9764 0.048 Uiso 1 1 calc R . . . .
C27 C 0.3157(4) -0.2049(13) 1.0256(3) 0.0450(14) Uani 1 1 d . . . . .
H27 H 0.3298 -0.3356 1.0671 0.054 Uiso 1 1 calc R . . . .
C28 C 0.2229(5) -0.0879(13) 1.0194(3) 0.0422(13) Uani 1 1 d . . . . .
H28 H 0.1754 -0.1439 1.0561 0.051 Uiso 1 1 calc R . . . .
C29 C 0.2007(4) 0.1107(13) 0.9593(3) 0.0347(11) Uani 1 1 d . . . . .
C30 C 0.1053(3) 0.2389(16) 0.9502(3) 0.0425(13) Uani 1 1 d . . . . .
H30 H 0.0563 0.1849 0.9857 0.051 Uiso 1 1 calc R . . . .
C31 C 0.0861(3) 0.4333(14) 0.8919(3) 0.0401(13) Uani 1 1 d . . . . .
H31 H 0.0243 0.5135 0.8887 0.048 Uiso 1 1 calc R . . . .
C32 C 0.1574(3) 0.5220(12) 0.8344(3) 0.0314(10) Uani 1 1 d . . . . .
C33 C 0.1381(3) 0.7280(13) 0.7738(3) 0.0343(10) Uani 1 1 d . . . . .
H33 H 0.0773 0.8152 0.7710 0.041 Uiso 1 1 calc R . . . .
C34 C 0.2092(3) 0.8043(12) 0.7175(3) 0.0335(11) Uani 1 1 d . . . . .
H34 H 0.1956 0.9397 0.6771 0.040 Uiso 1 1 calc R . . . .
C35 C 0.2519(3) 0.3990(11) 0.8401(2) 0.0245(9) Uani 1 1 d . . . . .
C36 C 0.2732(3) 0.1951(12) 0.9024(3) 0.0284(10) Uani 1 1 d . . . . .
H1 H 0.646(4) 0.892(7) 0.407(3) 0.026(13) Uiso 1 1 d D . . . .
H2 H 0.357(7) 0.878(13) 0.637(5) 0.12(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.392(5) . ?
C1 C2 1.391(7) . ?
C1 C14 1.388(7) . ?
C2 C3 1.447(6) . ?
C2 C15 1.418(6) . ?
C3 C4 1.361(7) . ?
C4 C5 1.424(7) . ?
C5 C6 1.404(7) . ?
C5 C16 1.422(7) . ?
C6 C7 1.384(8) . ?
C7 C8 1.375(10) . ?
C8 C9 1.383(9) . ?
C9 C10 1.426(7) . ?
C9 C16 1.442(6) . ?
C10 C11 1.341(8) . ?
C11 C12 1.437(7) . ?
C12 C13 1.398(7) . ?
C12 C15 1.420(6) . ?
C13 C14 1.382(7) . ?
C15 C16 1.418(7) . ?
O2 C21 1.377(5) . ?
C21 C22 1.402(7) . ?
C21 C34 1.387(6) . ?
C22 C23 1.437(6) . ?
C22 C35 1.414(6) . ?
C23 C24 1.359(8) . ?
C24 C25 1.415(7) . ?
C25 C26 1.414(7) . ?
C25 C36 1.426(7) . ?
C26 C27 1.372(8) . ?
C27 C28 1.390(9) . ?
C28 C29 1.380(8) . ?
C29 C30 1.447(8) . ?
C29 C36 1.428(6) . ?
C30 C31 1.338(9) . ?
C31 C32 1.428(7) . ?
C32 C33 1.400(7) . ?
C32 C35 1.421(6) . ?
C33 C34 1.399(7) . ?
C35 C36 1.420(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 116.2(4) . . ?
C14 C1 O1 122.3(4) . . ?
C14 C1 C2 121.5(4) . . ?
C1 C2 C3 121.8(4) . . ?
C1 C2 C15 118.7(4) . . ?
C15 C2 C3 119.5(4) . . ?
C4 C3 C2 119.8(4) . . ?
C3 C4 C5 122.2(5) . . ?
C6 C5 C4 123.1(5) . . ?
C6 C5 C16 118.4(4) . . ?
C16 C5 C4 118.4(4) . . ?
C7 C6 C5 120.6(6) . . ?
C8 C7 C6 121.4(6) . . ?
C7 C8 C9 121.0(5) . . ?
C8 C9 C10 123.6(5) . . ?
C8 C9 C16 118.8(5) . . ?
C10 C9 C16 117.6(5) . . ?
C11 C10 C9 122.8(4) . . ?
C10 C11 C12 121.1(5) . . ?
C13 C12 C11 122.6(5) . . ?
C13 C12 C15 119.1(4) . . ?
C15 C12 C11 118.3(5) . . ?
C14 C13 C12 120.8(4) . . ?
C13 C14 C1 120.1(5) . . ?
C2 C15 C12 119.9(4) . . ?
C16 C15 C2 119.5(4) . . ?
C16 C15 C12 120.6(4) . . ?
C5 C16 C9 119.8(5) . . ?
C15 C16 C5 120.5(4) . . ?
C15 C16 C9 119.7(4) . . ?
O2 C21 C22 116.8(4) . . ?
O2 C21 C34 120.9(4) . . ?
C34 C21 C22 122.1(4) . . ?
C21 C22 C23 122.6(4) . . ?
C21 C22 C35 118.2(4) . . ?
C35 C22 C23 119.2(4) . . ?
C24 C23 C22 120.2(4) . . ?
C23 C24 C25 122.2(5) . . ?
C24 C25 C36 118.5(4) . . ?
C26 C25 C24 123.0(5) . . ?
C26 C25 C36 118.4(5) . . ?
C27 C26 C25 120.9(5) . . ?
C26 C27 C28 120.9(5) . . ?
C29 C28 C27 120.6(5) . . ?
C28 C29 C30 122.8(5) . . ?
C28 C29 C36 119.9(5) . . ?
C36 C29 C30 117.4(5) . . ?
C31 C30 C29 121.5(4) . . ?
C30 C31 C32 122.2(5) . . ?
C33 C32 C31 122.5(4) . . ?
C33 C32 C35 119.1(4) . . ?
C35 C32 C31 118.4(5) . . ?
C34 C33 C32 120.8(4) . . ?
C21 C34 C33 119.4(4) . . ?
C22 C35 C32 120.4(4) . . ?
C22 C35 C36 119.8(4) . . ?
C36 C35 C32 119.8(4) . . ?
C25 C36 C29 119.3(5) . . ?
C35 C36 C25 120.0(4) . . ?
C35 C36 C29 120.8(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.455(3)
2 0.545(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_t100
_database_code_depnum_ccdc_archive 'CCDC 1892295'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7588(5)
_cell_length_b                   4.52816(13)
_cell_length_c                   16.5509(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.976(3)
_cell_angle_gamma                90
_cell_volume                     1031.16(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4299
_cell_measurement_temperature    104(6)
_cell_measurement_theta_max      74.4790
_cell_measurement_theta_min      5.3430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6094
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         2.670
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      104(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1016956000
_diffrn_orient_matrix_UB_12      -0.1409487000
_diffrn_orient_matrix_UB_13      0.0045367000
_diffrn_orient_matrix_UB_21      0.0008571000
_diffrn_orient_matrix_UB_22      -0.0344969000
_diffrn_orient_matrix_UB_23      -0.0926391000
_diffrn_orient_matrix_UB_31      0.0467720000
_diffrn_orient_matrix_UB_32      0.3076767000
_diffrn_orient_matrix_UB_33      -0.0082463000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.503
_reflns_Friedel_fraction_full    0.657
_reflns_Friedel_fraction_max     0.662
_reflns_number_gt                2932
_reflns_number_total             2985
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.545(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.043
_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)+(0.0944P)²+0.0515P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1225
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.455(3)
 0.545(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6404(2) 0.7292(8) 0.42691(16) 0.0225(6) Uani 1 1 d D . . . .
C1 C 0.7173(3) 0.6892(10) 0.4806(2) 0.0167(9) Uani 1 1 d . . . . .
C2 C 0.7007(3) 0.4892(10) 0.5431(2) 0.0156(8) Uani 1 1 d . . . . .
C3 C 0.6075(3) 0.3489(11) 0.5550(2) 0.0183(9) Uani 1 1 d . . . . .
H3 H 0.5562 0.3898 0.5201 0.022 Uiso 1 1 calc R . . . .
C4 C 0.5949(3) 0.1559(10) 0.6176(3) 0.0203(9) Uani 1 1 d . . . . .
H4 H 0.5345 0.0677 0.6248 0.024 Uiso 1 1 calc R . . . .
C5 C 0.6715(3) 0.0859(10) 0.6721(2) 0.0195(8) Uani 1 1 d . . . . .
C6 C 0.6600(3) -0.1124(12) 0.7369(3) 0.0271(10) Uani 1 1 d . . . . .
H6 H 0.6003 -0.2045 0.7448 0.032 Uiso 1 1 calc R . . . .
C7 C 0.7362(4) -0.1724(13) 0.7890(3) 0.0297(11) Uani 1 1 d . . . . .
H7 H 0.7274 -0.3071 0.8308 0.036 Uiso 1 1 calc R . . . .
C8 C 0.8256(4) -0.0341(12) 0.7797(3) 0.0306(11) Uani 1 1 d . . . . .
H8 H 0.8750 -0.0713 0.8166 0.037 Uiso 1 1 calc R . . . .
C9 C 0.8419(3) 0.1586(11) 0.7162(2) 0.0229(10) Uani 1 1 d . . . . .
C10 C 0.9334(3) 0.3026(11) 0.7028(3) 0.0229(10) Uani 1 1 d . . . . .
H10 H 0.9847 0.2648 0.7379 0.028 Uiso 1 1 calc R . . . .
C11 C 0.9474(3) 0.4908(12) 0.6407(3) 0.0225(10) Uani 1 1 d . . . . .
H11 H 1.0082 0.5767 0.6335 0.027 Uiso 1 1 calc R . . . .
C12 C 0.8704(3) 0.5615(10) 0.5856(2) 0.0185(9) Uani 1 1 d . . . . .
C13 C 0.8828(3) 0.7611(11) 0.5221(3) 0.0193(9) Uani 1 1 d . . . . .
H13 H 0.9425 0.8542 0.5151 0.023 Uiso 1 1 calc R . . . .
C14 C 0.8066(3) 0.8218(10) 0.4693(3) 0.0199(9) Uani 1 1 d . . . . .
H14 H 0.8159 0.9515 0.4264 0.024 Uiso 1 1 calc R . . . .
C15 C 0.7785(3) 0.4235(10) 0.5965(2) 0.0147(8) Uani 1 1 d . . . . .
C16 C 0.7631(3) 0.2256(12) 0.6620(2) 0.0189(9) Uani 1 1 d . . . . .
O2 O 0.3702(2) 0.7327(8) 0.66479(17) 0.0239(6) Uani 1 1 d D . . . .
C21 C 0.3006(3) 0.6780(10) 0.7227(2) 0.0173(9) Uani 1 1 d . . . . .
C22 C 0.3240(3) 0.4744(9) 0.7833(2) 0.0156(9) Uani 1 1 d . . . . .
C23 C 0.4197(3) 0.3461(11) 0.7913(3) 0.0188(9) Uani 1 1 d . . . . .
H23 H 0.4682 0.3966 0.7546 0.023 Uiso 1 1 calc R . . . .
C24 C 0.4394(3) 0.1536(10) 0.8515(3) 0.0213(9) Uani 1 1 d . . . . .
H24 H 0.5016 0.0745 0.8553 0.026 Uiso 1 1 calc R . . . .
C25 C 0.3685(3) 0.0683(10) 0.9089(2) 0.0200(9) Uani 1 1 d . . . . .
C26 C 0.3868(3) -0.1346(11) 0.9724(2) 0.0234(9) Uani 1 1 d . . . . .
H26 H 0.4484 -0.2169 0.9775 0.028 Uiso 1 1 calc R . . . .
C27 C 0.3156(3) -0.2119(11) 1.0263(3) 0.0255(10) Uani 1 1 d . . . . .
H27 H 0.3299 -0.3437 1.0677 0.031 Uiso 1 1 calc R . . . .
C28 C 0.2218(4) -0.0956(11) 1.0199(3) 0.0237(10) Uani 1 1 d . . . . .
H28 H 0.1739 -0.1530 1.0563 0.028 Uiso 1 1 calc R . . . .
C29 C 0.2004(3) 0.1061(11) 0.9592(2) 0.0207(9) Uani 1 1 d . . . . .
C30 C 0.1039(3) 0.2343(13) 0.9498(3) 0.0256(10) Uani 1 1 d . . . . .
H30 H 0.0547 0.1786 0.9853 0.031 Uiso 1 1 calc R . . . .
C31 C 0.0844(3) 0.4298(11) 0.8917(3) 0.0239(10) Uani 1 1 d . . . . .
H31 H 0.0222 0.5094 0.8883 0.029 Uiso 1 1 calc R . . . .
C32 C 0.1567(3) 0.5204(10) 0.8342(3) 0.0180(8) Uani 1 1 d . . . . .
C33 C 0.1375(3) 0.7285(10) 0.7738(2) 0.0202(8) Uani 1 1 d . . . . .
H33 H 0.0765 0.8162 0.7709 0.024 Uiso 1 1 calc R . . . .
C34 C 0.2089(3) 0.8058(11) 0.7178(2) 0.0204(9) Uani 1 1 d . . . . .
H34 H 0.1952 0.9423 0.6774 0.024 Uiso 1 1 calc R . . . .
C35 C 0.2518(3) 0.3987(10) 0.8406(2) 0.0138(8) Uani 1 1 d . . . . .
C36 C 0.2729(3) 0.1917(11) 0.9024(2) 0.0171(9) Uani 1 1 d . . . . .
H1 H 0.647(3) 0.899(6) 0.410(2) 0.010(11) Uiso 1 1 d D . . . .
H2 H 0.363(5) 0.887(10) 0.637(4) 0.06(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.394(5) . ?
C1 C2 1.394(6) . ?
C1 C14 1.380(6) . ?
C2 C3 1.445(6) . ?
C2 C15 1.419(5) . ?
C3 C4 1.367(6) . ?
C4 C5 1.424(6) . ?
C5 C6 1.407(6) . ?
C5 C16 1.419(6) . ?
C6 C7 1.385(7) . ?
C7 C8 1.389(8) . ?
C8 C9 1.384(7) . ?
C9 C10 1.435(6) . ?
C9 C16 1.441(6) . ?
C10 C11 1.348(7) . ?
C11 C12 1.434(6) . ?
C12 C13 1.397(6) . ?
C12 C15 1.422(5) . ?
C13 C14 1.393(6) . ?
C15 C16 1.422(6) . ?
O2 C21 1.377(5) . ?
C21 C22 1.400(6) . ?
C21 C34 1.390(6) . ?
C22 C23 1.445(5) . ?
C22 C35 1.415(5) . ?
C23 C24 1.351(6) . ?
C24 C25 1.416(6) . ?
C25 C26 1.419(7) . ?
C25 C36 1.432(6) . ?
C26 C27 1.369(7) . ?
C27 C28 1.398(7) . ?
C28 C29 1.390(7) . ?
C29 C30 1.457(6) . ?
C29 C36 1.425(6) . ?
C30 C31 1.335(7) . ?
C31 C32 1.436(6) . ?
C32 C33 1.399(6) . ?
C32 C35 1.425(5) . ?
C33 C34 1.394(6) . ?
C35 C36 1.417(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 115.7(4) . . ?
C14 C1 O1 122.2(4) . . ?
C14 C1 C2 121.9(4) . . ?
C1 C2 C3 122.1(4) . . ?
C1 C2 C15 118.4(4) . . ?
C15 C2 C3 119.5(4) . . ?
C4 C3 C2 119.8(4) . . ?
C3 C4 C5 121.9(4) . . ?
C6 C5 C4 122.8(4) . . ?
C6 C5 C16 118.3(4) . . ?
C16 C5 C4 118.9(4) . . ?
C7 C6 C5 121.0(5) . . ?
C6 C7 C8 120.9(5) . . ?
C9 C8 C7 120.8(4) . . ?
C8 C9 C10 123.1(4) . . ?
C8 C9 C16 118.9(4) . . ?
C10 C9 C16 117.9(4) . . ?
C11 C10 C9 122.0(4) . . ?
C10 C11 C12 121.4(4) . . ?
C13 C12 C11 122.2(4) . . ?
C13 C12 C15 119.2(4) . . ?
C15 C12 C11 118.6(4) . . ?
C14 C13 C12 120.5(4) . . ?
C1 C14 C13 119.9(4) . . ?
C2 C15 C12 120.0(4) . . ?
C2 C15 C16 119.7(4) . . ?
C16 C15 C12 120.4(4) . . ?
C5 C16 C9 120.1(4) . . ?
C5 C16 C15 120.2(3) . . ?
C15 C16 C9 119.7(4) . . ?
O2 C21 C22 117.2(4) . . ?
O2 C21 C34 121.0(4) . . ?
C34 C21 C22 121.7(4) . . ?
C21 C22 C23 122.7(4) . . ?
C21 C22 C35 118.6(4) . . ?
C35 C22 C23 118.7(4) . . ?
C24 C23 C22 120.7(4) . . ?
C23 C24 C25 122.2(4) . . ?
C24 C25 C26 123.5(4) . . ?
C24 C25 C36 118.4(4) . . ?
C26 C25 C36 118.1(4) . . ?
C27 C26 C25 121.4(4) . . ?
C26 C27 C28 120.9(4) . . ?
C29 C28 C27 119.9(4) . . ?
C28 C29 C30 122.2(4) . . ?
C28 C29 C36 120.4(4) . . ?
C36 C29 C30 117.4(4) . . ?
C31 C30 C29 121.6(4) . . ?
C30 C31 C32 121.8(4) . . ?
C33 C32 C31 122.4(4) . . ?
C33 C32 C35 119.1(4) . . ?
C35 C32 C31 118.5(4) . . ?
C34 C33 C32 120.8(4) . . ?
C21 C34 C33 119.7(4) . . ?
C22 C35 C32 120.1(4) . . ?
C22 C35 C36 120.0(3) . . ?
C36 C35 C32 119.8(4) . . ?
C29 C36 C25 119.2(4) . . ?
C35 C36 C25 120.0(4) . . ?
C35 C36 C29 120.8(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.455(3)
2 0.545(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_t90
_database_code_depnum_ccdc_archive 'CCDC 1892293'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7503(4)
_cell_length_b                   4.52597(12)
_cell_length_c                   16.5449(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.976(3)
_cell_angle_gamma                90
_cell_volume                     1029.65(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4341
_cell_measurement_temperature    90.1(4)
_cell_measurement_theta_max      74.6440
_cell_measurement_theta_min      4.1550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6070
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         2.671
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      90.1(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1017700000
_diffrn_orient_matrix_UB_12      -0.1410274000
_diffrn_orient_matrix_UB_13      -0.0045895000
_diffrn_orient_matrix_UB_21      -0.0008812000
_diffrn_orient_matrix_UB_22      -0.0347866000
_diffrn_orient_matrix_UB_23      0.0926581000
_diffrn_orient_matrix_UB_31      -0.0467728000
_diffrn_orient_matrix_UB_32      0.3078169000
_diffrn_orient_matrix_UB_33      0.0083205000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.501
_reflns_Friedel_fraction_full    0.655
_reflns_Friedel_fraction_max     0.660
_reflns_number_gt                2932
_reflns_number_total             2978
_reflns_odcompleteness_completeness 99.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.546(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.041
_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)+(0.0989P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1213
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.454(3)
 0.546(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6402(2) 0.7297(8) 0.42693(16) 0.0221(6) Uani 1 1 d D . . . .
C1 C 0.7171(3) 0.6885(10) 0.4805(2) 0.0170(9) Uani 1 1 d . . . . .
C2 C 0.7008(3) 0.4907(9) 0.5431(2) 0.0156(8) Uani 1 1 d . . . . .
C3 C 0.6073(3) 0.3488(10) 0.5550(2) 0.0180(8) Uani 1 1 d . . . . .
H3 H 0.5560 0.3889 0.5201 0.022 Uiso 1 1 calc R . . . .
C4 C 0.5948(3) 0.1563(10) 0.6177(2) 0.0201(9) Uani 1 1 d . . . . .
H4 H 0.5343 0.0686 0.6251 0.024 Uiso 1 1 calc R . . . .
C5 C 0.6718(3) 0.0856(10) 0.6721(2) 0.0191(8) Uani 1 1 d . . . . .
C6 C 0.6599(3) -0.1125(11) 0.7370(2) 0.0255(9) Uani 1 1 d . . . . .
H6 H 0.6001 -0.2037 0.7451 0.031 Uiso 1 1 calc R . . . .
C7 C 0.7362(4) -0.1735(12) 0.7890(2) 0.0289(10) Uani 1 1 d . . . . .
H7 H 0.7276 -0.3090 0.8306 0.035 Uiso 1 1 calc R . . . .
C8 C 0.8255(4) -0.0344(11) 0.7796(3) 0.0278(10) Uani 1 1 d . . . . .
H8 H 0.8751 -0.0719 0.8164 0.033 Uiso 1 1 calc R . . . .
C9 C 0.8419(3) 0.1595(10) 0.7161(2) 0.0218(9) Uani 1 1 d . . . . .
C10 C 0.9339(3) 0.3026(10) 0.7028(2) 0.0217(9) Uani 1 1 d . . . . .
H10 H 0.9853 0.2636 0.7378 0.026 Uiso 1 1 calc R . . . .
C11 C 0.9476(3) 0.4929(11) 0.6406(2) 0.0216(9) Uani 1 1 d . . . . .
H11 H 1.0082 0.5804 0.6335 0.026 Uiso 1 1 calc R . . . .
C12 C 0.8704(3) 0.5620(10) 0.5854(2) 0.0182(8) Uani 1 1 d . . . . .
C13 C 0.8828(3) 0.7609(10) 0.5219(2) 0.0194(9) Uani 1 1 d . . . . .
H13 H 0.9426 0.8534 0.5148 0.023 Uiso 1 1 calc R . . . .
C14 C 0.8066(3) 0.8227(9) 0.4689(3) 0.0188(9) Uani 1 1 d . . . . .
H14 H 0.8159 0.9530 0.4261 0.023 Uiso 1 1 calc R . . . .
C15 C 0.7784(3) 0.4235(10) 0.5964(2) 0.0147(8) Uani 1 1 d . . . . .
C16 C 0.7633(3) 0.2250(11) 0.6617(2) 0.0181(8) Uani 1 1 d . . . . .
O2 O 0.3704(2) 0.7333(8) 0.66484(16) 0.0227(6) Uani 1 1 d D . . . .
C21 C 0.3009(3) 0.6780(10) 0.7226(2) 0.0166(8) Uani 1 1 d . . . . .
C22 C 0.3237(3) 0.4746(9) 0.7832(2) 0.0153(8) Uani 1 1 d . . . . .
C23 C 0.4199(3) 0.3464(10) 0.7914(2) 0.0179(9) Uani 1 1 d . . . . .
H23 H 0.4685 0.3971 0.7548 0.022 Uiso 1 1 calc R . . . .
C24 C 0.4394(3) 0.1537(9) 0.8516(2) 0.0193(9) Uani 1 1 d . . . . .
H24 H 0.5016 0.0744 0.8555 0.023 Uiso 1 1 calc R . . . .
C25 C 0.3685(3) 0.0682(10) 0.9091(2) 0.0182(8) Uani 1 1 d . . . . .
C26 C 0.3870(3) -0.1358(11) 0.9724(2) 0.0222(9) Uani 1 1 d . . . . .
H26 H 0.4486 -0.2186 0.9775 0.027 Uiso 1 1 calc R . . . .
C27 C 0.3154(3) -0.2129(11) 1.0263(2) 0.0250(10) Uani 1 1 d . . . . .
H27 H 0.3296 -0.3450 1.0677 0.030 Uiso 1 1 calc R . . . .
C28 C 0.2214(3) -0.0961(10) 1.0200(2) 0.0225(9) Uani 1 1 d . . . . .
H28 H 0.1733 -0.1534 1.0563 0.027 Uiso 1 1 calc R . . . .
C29 C 0.2003(3) 0.1064(10) 0.9591(2) 0.0191(9) Uani 1 1 d . . . . .
C30 C 0.1037(3) 0.2335(12) 0.9501(3) 0.0237(9) Uani 1 1 d . . . . .
H30 H 0.0546 0.1778 0.9856 0.028 Uiso 1 1 calc R . . . .
C31 C 0.0843(3) 0.4288(11) 0.8917(2) 0.0228(9) Uani 1 1 d . . . . .
H31 H 0.0220 0.5075 0.8881 0.027 Uiso 1 1 calc R . . . .
C32 C 0.1567(3) 0.5211(10) 0.8343(2) 0.0177(8) Uani 1 1 d . . . . .
C33 C 0.1374(3) 0.7287(10) 0.7738(2) 0.0192(8) Uani 1 1 d . . . . .
H33 H 0.0764 0.8169 0.7709 0.023 Uiso 1 1 calc R . . . .
C34 C 0.2089(3) 0.8045(10) 0.7178(2) 0.0195(9) Uani 1 1 d . . . . .
H34 H 0.1950 0.9399 0.6771 0.023 Uiso 1 1 calc R . . . .
C35 C 0.2518(3) 0.3978(9) 0.8401(2) 0.0137(8) Uani 1 1 d . . . . .
C36 C 0.2728(3) 0.1916(11) 0.9024(2) 0.0166(9) Uani 1 1 d . . . . .
H1 H 0.650(3) 0.900(6) 0.411(2) 0.004(9) Uiso 1 1 d D . . . .
H2 H 0.361(4) 0.898(8) 0.643(3) 0.038(16) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.392(4) . ?
C1 C2 1.387(6) . ?
C1 C14 1.386(5) . ?
C2 C3 1.450(5) . ?
C2 C15 1.418(5) . ?
C3 C4 1.365(6) . ?
C4 C5 1.427(6) . ?
C5 C6 1.408(6) . ?
C5 C16 1.419(6) . ?
C6 C7 1.384(6) . ?
C7 C8 1.389(8) . ?
C8 C9 1.387(6) . ?
C9 C10 1.438(6) . ?
C9 C16 1.438(5) . ?
C10 C11 1.355(6) . ?
C11 C12 1.435(6) . ?
C12 C13 1.394(6) . ?
C12 C15 1.423(5) . ?
C13 C14 1.394(6) . ?
C15 C16 1.420(6) . ?
O2 C21 1.374(5) . ?
C21 C22 1.397(6) . ?
C21 C34 1.392(5) . ?
C22 C23 1.451(5) . ?
C22 C35 1.409(5) . ?
C23 C24 1.352(6) . ?
C24 C25 1.415(6) . ?
C25 C26 1.420(6) . ?
C25 C36 1.433(6) . ?
C26 C27 1.373(6) . ?
C27 C28 1.400(7) . ?
C28 C29 1.393(6) . ?
C29 C30 1.456(6) . ?
C29 C36 1.421(5) . ?
C30 C31 1.336(7) . ?
C31 C32 1.437(5) . ?
C32 C33 1.399(6) . ?
C32 C35 1.425(5) . ?
C33 C34 1.394(6) . ?
C35 C36 1.421(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 116.1(4) . . ?
C14 C1 O1 121.9(4) . . ?
C14 C1 C2 121.9(4) . . ?
C1 C2 C3 122.0(3) . . ?
C1 C2 C15 118.8(3) . . ?
C15 C2 C3 119.2(4) . . ?
C4 C3 C2 119.8(4) . . ?
C3 C4 C5 122.0(4) . . ?
C6 C5 C4 122.6(4) . . ?
C6 C5 C16 118.6(4) . . ?
C16 C5 C4 118.8(4) . . ?
C7 C6 C5 120.9(4) . . ?
C6 C7 C8 120.7(5) . . ?
C9 C8 C7 121.0(4) . . ?
C8 C9 C10 122.9(4) . . ?
C8 C9 C16 118.9(4) . . ?
C16 C9 C10 118.2(4) . . ?
C11 C10 C9 121.6(3) . . ?
C10 C11 C12 121.3(4) . . ?
C13 C12 C11 122.0(4) . . ?
C13 C12 C15 119.3(3) . . ?
C15 C12 C11 118.7(4) . . ?
C12 C13 C14 120.8(4) . . ?
C1 C14 C13 119.5(4) . . ?
C2 C15 C12 119.7(4) . . ?
C2 C15 C16 119.9(4) . . ?
C16 C15 C12 120.4(3) . . ?
C5 C16 C9 119.9(4) . . ?
C5 C16 C15 120.2(3) . . ?
C15 C16 C9 119.8(4) . . ?
O2 C21 C22 117.6(4) . . ?
O2 C21 C34 121.1(4) . . ?
C34 C21 C22 121.1(4) . . ?
C21 C22 C23 122.4(4) . . ?
C21 C22 C35 119.0(3) . . ?
C35 C22 C23 118.6(3) . . ?
C24 C23 C22 120.5(4) . . ?
C23 C24 C25 122.3(4) . . ?
C24 C25 C26 123.3(4) . . ?
C24 C25 C36 118.3(4) . . ?
C26 C25 C36 118.4(4) . . ?
C27 C26 C25 121.0(4) . . ?
C26 C27 C28 121.2(4) . . ?
C29 C28 C27 119.6(4) . . ?
C28 C29 C30 121.6(4) . . ?
C28 C29 C36 120.6(4) . . ?
C36 C29 C30 117.8(4) . . ?
C31 C30 C29 121.1(4) . . ?
C30 C31 C32 122.2(4) . . ?
C33 C32 C31 122.5(3) . . ?
C33 C32 C35 119.0(4) . . ?
C35 C32 C31 118.5(4) . . ?
C34 C33 C32 120.5(3) . . ?
C21 C34 C33 120.1(4) . . ?
C22 C35 C32 120.2(4) . . ?
C22 C35 C36 120.3(3) . . ?
C36 C35 C32 119.5(3) . . ?
C29 C36 C25 119.2(4) . . ?
C35 C36 C25 119.9(4) . . ?
C35 C36 C29 120.9(4) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9 0 1 0.1193 -8.9820 -0.0016 0.9839 0.9098 0.0991 0.4278
9 0 -1 0.0551 8.9820 0.0016 -0.9839 -0.9098 -0.0991 -0.4278
-1 3 1 0.1820 -1.0002 2.9998 1.0284 -0.3260 -0.0082 0.9787
1 -3 -1 0.2887 1.0002 -2.9998 -1.0284 0.3260 0.0082 -0.9787
-6 -2 0 0.2727 -5.9868 -2.0010 -0.0309 0.8916 0.0720 -0.3362
0 0 11 0.0232 0.0385 -0.0028 10.9929 -0.0540 1.0186 0.0888
0 0 -11 0.0361 -0.0385 0.0028 -10.9929 0.0540 -1.0186 -0.0888
-6 -2 1 0.2655 -5.9833 -2.0013 0.9685 0.8867 0.1646 -0.3281

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.454(3)
2 0.546(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_t180
_database_code_depnum_ccdc_archive 'CCDC 1892298'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7934(4)
_cell_length_b                   4.54536(12)
_cell_length_c                   16.5872(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.979(3)
_cell_angle_gamma                90
_cell_volume                     1039.95(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4021
_cell_measurement_temperature    179.97(10)
_cell_measurement_theta_max      75.1580
_cell_measurement_theta_min      2.6590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6153
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.052
_diffrn_reflns_theta_min         2.664
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1013924000
_diffrn_orient_matrix_UB_12      -0.1411450000
_diffrn_orient_matrix_UB_13      -0.0040097000
_diffrn_orient_matrix_UB_21      -0.0005899000
_diffrn_orient_matrix_UB_22      -0.0317671000
_diffrn_orient_matrix_UB_23      0.0925061000
_diffrn_orient_matrix_UB_31      -0.0468013000
_diffrn_orient_matrix_UB_32      0.3064144000
_diffrn_orient_matrix_UB_33      0.0076690000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.514
_reflns_Friedel_fraction_full    0.665
_reflns_Friedel_fraction_max     0.676
_reflns_number_gt                2920
_reflns_number_total             3010
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.544(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.031
_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)+(0.0956P)²+0.0365P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.456(3)
 0.544(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6412(2) 0.7266(8) 0.42720(17) 0.0351(7) Uani 1 1 d D . . . .
C1 C 0.7176(3) 0.6856(10) 0.4808(2) 0.0278(9) Uani 1 1 d . . . . .
C2 C 0.7013(3) 0.4877(10) 0.5432(2) 0.0252(8) Uani 1 1 d . . . . .
C3 C 0.6081(3) 0.3473(11) 0.5548(2) 0.0293(9) Uani 1 1 d . . . . .
H3 H 0.5571 0.3878 0.5199 0.035 Uiso 1 1 calc R . . . .
C4 C 0.5955(3) 0.1557(11) 0.6171(3) 0.0333(10) Uani 1 1 d . . . . .
H4 H 0.5351 0.0681 0.6241 0.040 Uiso 1 1 calc R . . . .
C5 C 0.6714(3) 0.0851(10) 0.6719(2) 0.0304(9) Uani 1 1 d . . . . .
C6 C 0.6596(4) -0.1126(12) 0.7364(3) 0.0428(11) Uani 1 1 d . . . . .
H6 H 0.6003 -0.2062 0.7440 0.051 Uiso 1 1 calc R . . . .
C7 C 0.7356(5) -0.1687(15) 0.7887(3) 0.0514(14) Uani 1 1 d . . . . .
H7 H 0.7267 -0.3014 0.8307 0.062 Uiso 1 1 calc R . . . .
C8 C 0.8240(5) -0.0329(13) 0.7799(3) 0.0490(14) Uani 1 1 d . . . . .
H8 H 0.8731 -0.0701 0.8170 0.059 Uiso 1 1 calc R . . . .
C9 C 0.8407(3) 0.1582(11) 0.7166(3) 0.0366(11) Uani 1 1 d . . . . .
C10 C 0.9318(3) 0.3014(13) 0.7029(3) 0.0414(12) Uani 1 1 d . . . . .
H10 H 0.9829 0.2631 0.7379 0.050 Uiso 1 1 calc R . . . .
C11 C 0.9462(3) 0.4887(12) 0.6414(3) 0.0374(11) Uani 1 1 d . . . . .
H11 H 1.0068 0.5748 0.6348 0.045 Uiso 1 1 calc R . . . .
C12 C 0.8702(3) 0.5589(10) 0.5859(2) 0.0293(9) Uani 1 1 d . . . . .
C13 C 0.8827(3) 0.7577(11) 0.5229(3) 0.0343(10) Uani 1 1 d . . . . .
H13 H 0.9422 0.8505 0.5160 0.041 Uiso 1 1 calc R . . . .
C14 C 0.8071(3) 0.8189(11) 0.4701(3) 0.0332(10) Uani 1 1 d . . . . .
H14 H 0.8166 0.9493 0.4276 0.040 Uiso 1 1 calc R . . . .
C15 C 0.7782(3) 0.4224(11) 0.5964(2) 0.0250(9) Uani 1 1 d . . . . .
C16 C 0.7629(3) 0.2250(12) 0.6616(2) 0.0290(9) Uani 1 1 d . . . . .
O2 O 0.3696(2) 0.7292(9) 0.66467(18) 0.0374(7) Uani 1 1 d D . . . .
C21 C 0.3004(3) 0.6767(10) 0.7225(2) 0.0286(9) Uani 1 1 d . . . . .
C22 C 0.3240(3) 0.4732(9) 0.7834(3) 0.0265(9) Uani 1 1 d . . . . .
C23 C 0.4191(3) 0.3453(11) 0.7906(3) 0.0300(10) Uani 1 1 d . . . . .
H23 H 0.4672 0.3938 0.7536 0.036 Uiso 1 1 calc R . . . .
C24 C 0.4387(3) 0.1552(11) 0.8510(3) 0.0365(11) Uani 1 1 d . . . . .
H24 H 0.5009 0.0771 0.8552 0.044 Uiso 1 1 calc R . . . .
C25 C 0.3676(3) 0.0712(10) 0.9081(3) 0.0319(9) Uani 1 1 d . . . . .
C26 C 0.3866(4) -0.1305(12) 0.9718(3) 0.0389(11) Uani 1 1 d . . . . .
H26 H 0.4481 -0.2123 0.9768 0.047 Uiso 1 1 calc R . . . .
C27 C 0.3158(4) -0.2063(12) 1.0260(3) 0.0437(12) Uani 1 1 d . . . . .
H27 H 0.3300 -0.3372 1.0674 0.052 Uiso 1 1 calc R . . . .
C28 C 0.2229(4) -0.0894(12) 1.0196(3) 0.0398(11) Uani 1 1 d . . . . .
H28 H 0.1753 -0.1457 1.0562 0.048 Uiso 1 1 calc R . . . .
C29 C 0.2006(3) 0.1104(12) 0.9592(3) 0.0344(10) Uani 1 1 d . . . . .
C30 C 0.1053(3) 0.2380(14) 0.9500(3) 0.0413(11) Uani 1 1 d . . . . .
H30 H 0.0563 0.1832 0.9855 0.050 Uiso 1 1 calc R . . . .
C31 C 0.0858(3) 0.4329(13) 0.8919(3) 0.0388(12) Uani 1 1 d . . . . .
H31 H 0.0238 0.5129 0.8888 0.047 Uiso 1 1 calc R . . . .
C32 C 0.1571(3) 0.5222(11) 0.8343(3) 0.0317(9) Uani 1 1 d . . . . .
C33 C 0.1380(3) 0.7285(11) 0.7737(3) 0.0334(9) Uani 1 1 d . . . . .
H33 H 0.0772 0.8159 0.7707 0.040 Uiso 1 1 calc R . . . .
C34 C 0.2092(3) 0.8046(11) 0.7177(3) 0.0326(9) Uani 1 1 d . . . . .
H34 H 0.1957 0.9405 0.6773 0.039 Uiso 1 1 calc R . . . .
C35 C 0.2518(3) 0.3992(10) 0.8403(2) 0.0245(8) Uani 1 1 d . . . . .
C36 C 0.2734(3) 0.1948(11) 0.9022(2) 0.0285(9) Uani 1 1 d . . . . .
H1 H 0.647(3) 0.894(6) 0.408(2) 0.026(12) Uiso 1 1 d D . . . .
H2 H 0.360(6) 0.876(13) 0.635(4) 0.12(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.392(5) . ?
C1 C2 1.389(6) . ?
C1 C14 1.386(6) . ?
C2 C3 1.449(6) . ?
C2 C15 1.411(5) . ?
C3 C4 1.363(6) . ?
C4 C5 1.423(6) . ?
C5 C6 1.407(6) . ?
C5 C16 1.424(6) . ?
C6 C7 1.385(8) . ?
C7 C8 1.374(9) . ?
C8 C9 1.382(8) . ?
C9 C10 1.432(7) . ?
C9 C16 1.441(6) . ?
C10 C11 1.343(7) . ?
C11 C12 1.432(6) . ?
C12 C13 1.392(7) . ?
C12 C15 1.424(6) . ?
C13 C14 1.389(6) . ?
C15 C16 1.422(6) . ?
O2 C21 1.374(5) . ?
C21 C22 1.408(7) . ?
C21 C34 1.387(6) . ?
C22 C23 1.440(6) . ?
C22 C35 1.412(6) . ?
C23 C24 1.350(7) . ?
C24 C25 1.416(6) . ?
C25 C26 1.423(7) . ?
C25 C36 1.420(7) . ?
C26 C27 1.371(7) . ?
C27 C28 1.391(8) . ?
C28 C29 1.387(7) . ?
C29 C30 1.444(7) . ?
C29 C36 1.431(6) . ?
C30 C31 1.337(8) . ?
C31 C32 1.430(6) . ?
C32 C33 1.400(7) . ?
C32 C35 1.424(6) . ?
C33 C34 1.395(6) . ?
C35 C36 1.416(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 116.1(4) . . ?
C14 C1 O1 122.3(4) . . ?
C14 C1 C2 121.5(4) . . ?
C1 C2 C3 121.9(4) . . ?
C1 C2 C15 118.7(4) . . ?
C15 C2 C3 119.4(4) . . ?
C4 C3 C2 119.7(4) . . ?
C3 C4 C5 122.3(4) . . ?
C4 C5 C16 118.4(4) . . ?
C6 C5 C4 123.0(4) . . ?
C6 C5 C16 118.6(4) . . ?
C7 C6 C5 120.4(5) . . ?
C8 C7 C6 121.5(5) . . ?
C7 C8 C9 120.7(5) . . ?
C8 C9 C10 123.5(4) . . ?
C8 C9 C16 119.3(5) . . ?
C10 C9 C16 117.2(4) . . ?
C11 C10 C9 122.6(4) . . ?
C10 C11 C12 121.4(4) . . ?
C13 C12 C11 122.5(4) . . ?
C13 C12 C15 119.0(4) . . ?
C15 C12 C11 118.5(4) . . ?
C14 C13 C12 120.7(4) . . ?
C1 C14 C13 120.0(4) . . ?
C2 C15 C12 120.1(4) . . ?
C2 C15 C16 119.9(4) . . ?
C16 C15 C12 120.0(4) . . ?
C5 C16 C9 119.4(4) . . ?
C15 C16 C5 120.3(3) . . ?
C15 C16 C9 120.3(4) . . ?
O2 C21 C22 117.0(4) . . ?
O2 C21 C34 121.1(4) . . ?
C34 C21 C22 121.7(4) . . ?
C21 C22 C23 122.4(4) . . ?
C21 C22 C35 118.2(4) . . ?
C35 C22 C23 119.4(4) . . ?
C24 C23 C22 120.2(4) . . ?
C23 C24 C25 122.0(4) . . ?
C24 C25 C26 122.9(4) . . ?
C24 C25 C36 118.7(4) . . ?
C36 C25 C26 118.3(4) . . ?
C27 C26 C25 121.2(5) . . ?
C26 C27 C28 120.7(5) . . ?
C29 C28 C27 120.7(5) . . ?
C28 C29 C30 122.7(4) . . ?
C28 C29 C36 119.8(5) . . ?
C36 C29 C30 117.4(4) . . ?
C31 C30 C29 121.7(4) . . ?
C30 C31 C32 122.1(4) . . ?
C33 C32 C31 122.7(4) . . ?
C33 C32 C35 119.1(4) . . ?
C35 C32 C31 118.2(4) . . ?
C34 C33 C32 120.8(4) . . ?
C21 C34 C33 119.7(4) . . ?
C22 C35 C32 120.4(4) . . ?
C22 C35 C36 119.5(4) . . ?
C36 C35 C32 120.1(4) . . ?
C25 C36 C29 119.4(4) . . ?
C35 C36 C25 120.2(4) . . ?
C35 C36 C29 120.5(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.456(3)
2 0.544(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_t170
_database_code_depnum_ccdc_archive 'CCDC 1892297'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7896(5)
_cell_length_b                   4.54222(14)
_cell_length_c                   16.5883(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.976(3)
_cell_angle_gamma                90
_cell_volume                     1039.02(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    170.03(10)
_cell_measurement_theta_max      76.0420
_cell_measurement_theta_min      4.1420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6152
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         2.664
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1014383000
_diffrn_orient_matrix_UB_12      -0.1406804000
_diffrn_orient_matrix_UB_13      -0.0044280000
_diffrn_orient_matrix_UB_21      -0.0010681000
_diffrn_orient_matrix_UB_22      -0.0323621000
_diffrn_orient_matrix_UB_23      0.0924979000
_diffrn_orient_matrix_UB_31      -0.0467109000
_diffrn_orient_matrix_UB_32      0.3068372000
_diffrn_orient_matrix_UB_33      0.0076573000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.512
_reflns_Friedel_fraction_full    0.662
_reflns_Friedel_fraction_max     0.673
_reflns_number_gt                2920
_reflns_number_total             3006
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.545(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.050
_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)+(0.0920P)²+0.0635P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1272
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.455(3)
 0.545(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6412(2) 0.7273(8) 0.42715(17) 0.0333(7) Uani 1 1 d D . . . .
C1 C 0.7175(3) 0.6858(11) 0.4808(2) 0.0268(9) Uani 1 1 d . . . . .
C2 C 0.7011(3) 0.4879(11) 0.5433(2) 0.0244(9) Uani 1 1 d . . . . .
C3 C 0.6080(3) 0.3472(11) 0.5550(2) 0.0281(10) Uani 1 1 d . . . . .
H3 H 0.5570 0.3873 0.5201 0.034 Uiso 1 1 calc R . . . .
C4 C 0.5954(3) 0.1562(11) 0.6173(3) 0.0306(10) Uani 1 1 d . . . . .
H4 H 0.5349 0.0691 0.6244 0.037 Uiso 1 1 calc R . . . .
C5 C 0.6713(4) 0.0851(11) 0.6718(3) 0.0300(9) Uani 1 1 d . . . . .
C6 C 0.6597(4) -0.1112(13) 0.7364(3) 0.0412(11) Uani 1 1 d . . . . .
H6 H 0.6002 -0.2031 0.7441 0.049 Uiso 1 1 calc R . . . .
C7 C 0.7352(5) -0.1705(15) 0.7887(3) 0.0486(14) Uani 1 1 d . . . . .
H7 H 0.7259 -0.3042 0.8304 0.058 Uiso 1 1 calc R . . . .
C8 C 0.8245(5) -0.0343(14) 0.7800(3) 0.0462(14) Uani 1 1 d . . . . .
H8 H 0.8736 -0.0720 0.8169 0.055 Uiso 1 1 calc R . . . .
C9 C 0.8410(3) 0.1591(12) 0.7162(3) 0.0349(11) Uani 1 1 d . . . . .
C10 C 0.9322(3) 0.3017(12) 0.7029(3) 0.0368(12) Uani 1 1 d . . . . .
H10 H 0.9833 0.2635 0.7380 0.044 Uiso 1 1 calc R . . . .
C11 C 0.9464(3) 0.4896(13) 0.6412(3) 0.0361(11) Uani 1 1 d . . . . .
H11 H 1.0070 0.5762 0.6345 0.043 Uiso 1 1 calc R . . . .
C12 C 0.8702(3) 0.5589(11) 0.5859(2) 0.0278(9) Uani 1 1 d . . . . .
C13 C 0.8825(3) 0.7581(12) 0.5226(3) 0.0318(10) Uani 1 1 d . . . . .
H13 H 0.9420 0.8511 0.5157 0.038 Uiso 1 1 calc R . . . .
C14 C 0.8070(3) 0.8187(11) 0.4700(3) 0.0307(10) Uani 1 1 d . . . . .
H14 H 0.8165 0.9489 0.4275 0.037 Uiso 1 1 calc R . . . .
C15 C 0.7782(3) 0.4222(11) 0.5963(2) 0.0243(9) Uani 1 1 d . . . . .
C16 C 0.7630(3) 0.2254(12) 0.6619(2) 0.0276(9) Uani 1 1 d . . . . .
O2 O 0.3698(2) 0.7300(9) 0.66470(18) 0.0354(7) Uani 1 1 d D . . . .
C21 C 0.3003(3) 0.6761(11) 0.7228(2) 0.0271(9) Uani 1 1 d . . . . .
C22 C 0.3239(3) 0.4743(10) 0.7828(3) 0.0247(9) Uani 1 1 d . . . . .
C23 C 0.4191(3) 0.3456(11) 0.7908(3) 0.0291(10) Uani 1 1 d . . . . .
H23 H 0.4674 0.3950 0.7540 0.035 Uiso 1 1 calc R . . . .
C24 C 0.4391(3) 0.1540(11) 0.8510(3) 0.0331(11) Uani 1 1 d . . . . .
H24 H 0.5011 0.0749 0.8548 0.040 Uiso 1 1 calc R . . . .
C25 C 0.3680(3) 0.0704(11) 0.9085(3) 0.0301(9) Uani 1 1 d . . . . .
C26 C 0.3869(4) -0.1320(12) 0.9717(3) 0.0364(11) Uani 1 1 d . . . . .
H26 H 0.4482 -0.2153 0.9764 0.044 Uiso 1 1 calc R . . . .
C27 C 0.3157(4) -0.2067(12) 1.0260(3) 0.0412(12) Uani 1 1 d . . . . .
H27 H 0.3299 -0.3372 1.0675 0.049 Uiso 1 1 calc R . . . .
C28 C 0.2228(4) -0.0898(12) 1.0197(3) 0.0374(11) Uani 1 1 d . . . . .
H28 H 0.1752 -0.1460 1.0564 0.045 Uiso 1 1 calc R . . . .
C29 C 0.2005(3) 0.1100(12) 0.9592(3) 0.0315(10) Uani 1 1 d . . . . .
C30 C 0.1051(3) 0.2376(14) 0.9502(3) 0.0386(11) Uani 1 1 d . . . . .
H30 H 0.0562 0.1830 0.9858 0.046 Uiso 1 1 calc R . . . .
C31 C 0.0852(3) 0.4320(13) 0.8919(3) 0.0378(12) Uani 1 1 d . . . . .
H31 H 0.0231 0.5110 0.8885 0.045 Uiso 1 1 calc R . . . .
C32 C 0.1574(3) 0.5224(11) 0.8342(3) 0.0286(9) Uani 1 1 d . . . . .
C33 C 0.1381(3) 0.7291(11) 0.7739(3) 0.0313(9) Uani 1 1 d . . . . .
H33 H 0.0774 0.8174 0.7712 0.038 Uiso 1 1 calc R . . . .
C34 C 0.2093(3) 0.8043(12) 0.7176(3) 0.0318(10) Uani 1 1 d . . . . .
H34 H 0.1958 0.9392 0.6770 0.038 Uiso 1 1 calc R . . . .
C35 C 0.2516(3) 0.3998(10) 0.8404(2) 0.0226(8) Uani 1 1 d . . . . .
C36 C 0.2733(3) 0.1939(11) 0.9022(2) 0.0260(9) Uani 1 1 d . . . . .
H1 H 0.648(3) 0.893(7) 0.406(2) 0.024(12) Uiso 1 1 d D . . . .
H2 H 0.357(8) 0.881(14) 0.638(5) 0.15(5) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.391(5) . ?
C1 C2 1.391(7) . ?
C1 C14 1.386(6) . ?
C2 C3 1.446(6) . ?
C2 C15 1.412(5) . ?
C3 C4 1.360(7) . ?
C4 C5 1.421(6) . ?
C5 C6 1.403(7) . ?
C5 C16 1.425(7) . ?
C6 C7 1.382(8) . ?
C7 C8 1.386(10) . ?
C8 C9 1.394(8) . ?
C9 C10 1.432(7) . ?
C9 C16 1.436(6) . ?
C10 C11 1.347(7) . ?
C11 C12 1.431(6) . ?
C12 C13 1.396(7) . ?
C12 C15 1.423(6) . ?
C13 C14 1.386(6) . ?
C15 C16 1.423(7) . ?
O2 C21 1.380(5) . ?
C21 C22 1.392(7) . ?
C21 C34 1.386(6) . ?
C22 C23 1.443(6) . ?
C22 C35 1.421(6) . ?
C23 C24 1.353(7) . ?
C24 C25 1.420(6) . ?
C25 C26 1.419(7) . ?
C25 C36 1.425(7) . ?
C26 C27 1.374(7) . ?
C27 C28 1.391(8) . ?
C28 C29 1.388(7) . ?
C29 C30 1.446(7) . ?
C29 C36 1.429(6) . ?
C30 C31 1.338(8) . ?
C31 C32 1.440(6) . ?
C32 C33 1.398(7) . ?
C32 C35 1.418(6) . ?
C33 C34 1.397(6) . ?
C35 C36 1.421(6) . ?

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 C1 C2 116.2(4) . . ?
C14 C1 O1 122.2(4) . . ?
C14 C1 C2 121.5(4) . . ?
C1 C2 C3 122.0(4) . . ?
C1 C2 C15 118.6(4) . . ?
C15 C2 C3 119.4(4) . . ?
C4 C3 C2 119.8(4) . . ?
C3 C4 C5 122.3(4) . . ?
C4 C5 C16 118.6(4) . . ?
C6 C5 C4 123.1(5) . . ?
C6 C5 C16 118.3(4) . . ?
C7 C6 C5 121.2(5) . . ?
C6 C7 C8 121.1(5) . . ?
C7 C8 C9 120.4(5) . . ?
C8 C9 C10 123.0(4) . . ?
C8 C9 C16 119.1(5) . . ?
C10 C9 C16 117.9(4) . . ?
C11 C10 C9 122.0(4) . . ?
C10 C11 C12 121.4(4) . . ?
C13 C12 C11 122.4(4) . . ?
C13 C12 C15 118.9(4) . . ?
C15 C12 C11 118.7(4) . . ?
C14 C13 C12 120.7(4) . . ?
C13 C14 C1 120.1(4) . . ?
C2 C15 C12 120.2(4) . . ?
C2 C15 C16 119.9(4) . . ?
C16 C15 C12 119.9(4) . . ?
C5 C16 C9 119.9(4) . . ?
C15 C16 C5 120.0(4) . . ?
C15 C16 C9 120.0(4) . . ?
O2 C21 C22 117.0(4) . . ?
O2 C21 C34 120.7(4) . . ?
C34 C21 C22 122.2(4) . . ?
C21 C22 C23 123.0(4) . . ?
C21 C22 C35 118.3(4) . . ?
C35 C22 C23 118.7(4) . . ?
C24 C23 C22 120.9(4) . . ?
C23 C24 C25 121.8(4) . . ?
C24 C25 C36 118.6(4) . . ?
C26 C25 C24 122.9(4) . . ?
C26 C25 C36 118.5(4) . . ?
C27 C26 C25 120.9(5) . . ?
C26 C27 C28 121.0(5) . . ?
C29 C28 C27 120.5(5) . . ?
C28 C29 C30 122.6(4) . . ?
C28 C29 C36 119.8(5) . . ?
C36 C29 C30 117.6(5) . . ?
C31 C30 C29 121.8(4) . . ?
C30 C31 C32 121.7(4) . . ?
C33 C32 C31 122.4(4) . . ?
C33 C32 C35 119.4(4) . . ?
C35 C32 C31 118.3(4) . . ?
C34 C33 C32 120.6(4) . . ?
C21 C34 C33 119.5(4) . . ?
C32 C35 C22 120.1(4) . . ?
C32 C35 C36 120.3(4) . . ?
C36 C35 C22 119.7(4) . . ?
C25 C36 C29 119.3(4) . . ?
C35 C36 C25 120.3(4) . . ?
C35 C36 C29 120.4(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.455(3)
2 0.545(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_t200
_database_code_depnum_ccdc_archive 'CCDC 1892300'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8039(5)
_cell_length_b                   4.55103(13)
_cell_length_c                   16.6046(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.998(3)
_cell_angle_gamma                90
_cell_volume                     1043.14(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3877
_cell_measurement_temperature    199.97(10)
_cell_measurement_theta_max      76.1560
_cell_measurement_theta_min      2.6570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6188
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.014
_diffrn_reflns_theta_min         2.661
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1012964000
_diffrn_orient_matrix_UB_12      0.1411038000
_diffrn_orient_matrix_UB_13      -0.0038878000
_diffrn_orient_matrix_UB_21      0.0004632000
_diffrn_orient_matrix_UB_22      0.0312264000
_diffrn_orient_matrix_UB_23      0.0924184000
_diffrn_orient_matrix_UB_31      0.0467934000
_diffrn_orient_matrix_UB_32      -0.3060492000
_diffrn_orient_matrix_UB_33      0.0075846000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.517
_reflns_Friedel_fraction_full    0.667
_reflns_Friedel_fraction_max     0.680
_reflns_number_gt                2912
_reflns_number_total             3015
_reflns_odcompleteness_completeness 99.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.457(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.034
_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)+(0.0914P)²+0.0791P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1287
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.543(3)
 0.457(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6419(2) 0.7262(9) 0.42721(18) 0.0382(7) Uani 1 1 d D . . . .
C1 C 0.7177(3) 0.6849(12) 0.4810(2) 0.0305(10) Uani 1 1 d . . . . .
C2 C 0.7015(3) 0.4872(11) 0.5436(3) 0.0271(9) Uani 1 1 d . . . . .
C3 C 0.6084(3) 0.3474(11) 0.5549(2) 0.0319(10) Uani 1 1 d . . . . .
H3 H 0.5577 0.3877 0.5198 0.038 Uiso 1 1 calc R . . . .
C4 C 0.5953(3) 0.1557(12) 0.6173(3) 0.0357(11) Uani 1 1 d . . . . .
H4 H 0.5349 0.0689 0.6244 0.043 Uiso 1 1 calc R . . . .
C5 C 0.6713(4) 0.0852(11) 0.6718(3) 0.0335(10) Uani 1 1 d . . . . .
C6 C 0.6597(4) -0.1108(14) 0.7364(3) 0.0463(12) Uani 1 1 d . . . . .
H6 H 0.6003 -0.2033 0.7441 0.056 Uiso 1 1 calc R . . . .
C7 C 0.7354(5) -0.1685(16) 0.7887(3) 0.0556(16) Uani 1 1 d . . . . .
H7 H 0.7262 -0.3009 0.8307 0.067 Uiso 1 1 calc R . . . .
C8 C 0.8241(5) -0.0331(14) 0.7798(3) 0.0528(15) Uani 1 1 d . . . . .
H8 H 0.8733 -0.0705 0.8166 0.063 Uiso 1 1 calc R . . . .
C9 C 0.8406(4) 0.1578(12) 0.7164(3) 0.0394(12) Uani 1 1 d . . . . .
C10 C 0.9316(4) 0.3012(13) 0.7033(3) 0.0431(13) Uani 1 1 d . . . . .
H10 H 0.9825 0.2633 0.7385 0.052 Uiso 1 1 calc R . . . .
C11 C 0.9459(3) 0.4889(14) 0.6418(3) 0.0420(12) Uani 1 1 d . . . . .
H11 H 1.0064 0.5759 0.6354 0.050 Uiso 1 1 calc R . . . .
C12 C 0.8700(3) 0.5576(11) 0.5860(3) 0.0321(10) Uani 1 1 d . . . . .
C13 C 0.8824(3) 0.7562(12) 0.5229(3) 0.0364(11) Uani 1 1 d . . . . .
H13 H 0.9419 0.8486 0.5160 0.044 Uiso 1 1 calc R . . . .
C14 C 0.8071(3) 0.8177(12) 0.4703(3) 0.0353(11) Uani 1 1 d . . . . .
H14 H 0.8166 0.9479 0.4278 0.042 Uiso 1 1 calc R . . . .
C15 C 0.7781(3) 0.4218(11) 0.5970(2) 0.0270(9) Uani 1 1 d . . . . .
C16 C 0.7628(3) 0.2257(13) 0.6621(3) 0.0316(9) Uani 1 1 d . . . . .
O2 O 0.3694(3) 0.7285(9) 0.66461(19) 0.0401(7) Uani 1 1 d D . . . .
C21 C 0.3001(3) 0.6764(11) 0.7227(2) 0.0304(10) Uani 1 1 d . . . . .
C22 C 0.3239(3) 0.4731(10) 0.7830(3) 0.0282(9) Uani 1 1 d . . . . .
C23 C 0.4188(3) 0.3460(12) 0.7905(3) 0.0333(10) Uani 1 1 d . . . . .
H23 H 0.4668 0.3957 0.7537 0.040 Uiso 1 1 calc R . . . .
C24 C 0.4388(3) 0.1543(11) 0.8508(3) 0.0384(11) Uani 1 1 d . . . . .
H24 H 0.5007 0.0753 0.8545 0.046 Uiso 1 1 calc R . . . .
C25 C 0.3680(3) 0.0709(11) 0.9082(3) 0.0343(10) Uani 1 1 d . . . . .
C26 C 0.3868(4) -0.1305(13) 0.9715(3) 0.0424(12) Uani 1 1 d . . . . .
H26 H 0.4481 -0.2137 0.9763 0.051 Uiso 1 1 calc R . . . .
C27 C 0.3156(4) -0.2041(13) 1.0256(3) 0.0468(13) Uani 1 1 d . . . . .
H27 H 0.3297 -0.3352 1.0670 0.056 Uiso 1 1 calc R . . . .
C28 C 0.2228(4) -0.0866(13) 1.0200(3) 0.0429(12) Uani 1 1 d . . . . .
H28 H 0.1754 -0.1411 1.0569 0.051 Uiso 1 1 calc R . . . .
C29 C 0.2010(4) 0.1115(13) 0.9593(3) 0.0370(11) Uani 1 1 d . . . . .
C30 C 0.1054(3) 0.2399(15) 0.9501(3) 0.0440(12) Uani 1 1 d . . . . .
H30 H 0.0564 0.1857 0.9856 0.053 Uiso 1 1 calc R . . . .
C31 C 0.0862(3) 0.4337(14) 0.8920(3) 0.0429(13) Uani 1 1 d . . . . .
H31 H 0.0244 0.5140 0.8890 0.051 Uiso 1 1 calc R . . . .
C32 C 0.1575(3) 0.5230(11) 0.8341(3) 0.0334(10) Uani 1 1 d . . . . .
C33 C 0.1383(3) 0.7279(12) 0.7739(3) 0.0359(10) Uani 1 1 d . . . . .
H33 H 0.0775 0.8153 0.7711 0.043 Uiso 1 1 calc R . . . .
C34 C 0.2094(3) 0.8035(12) 0.7178(3) 0.0357(10) Uani 1 1 d . . . . .
H34 H 0.1958 0.9388 0.6774 0.043 Uiso 1 1 calc R . . . .
C35 C 0.2520(3) 0.4000(10) 0.8404(2) 0.0261(9) Uani 1 1 d . . . . .
C36 C 0.2735(3) 0.1946(12) 0.9023(2) 0.0298(9) Uani 1 1 d . . . . .
H1 H 0.646(4) 0.893(7) 0.408(3) 0.040(15) Uiso 1 1 d D . . . .
H2 H 0.359(7) 0.880(13) 0.637(5) 0.14(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.388(5) . ?
C1 C2 1.394(7) . ?
C1 C14 1.386(7) . ?
C2 C3 1.446(6) . ?
C2 C15 1.411(5) . ?
C3 C4 1.367(7) . ?
C4 C5 1.421(7) . ?
C5 C6 1.404(7) . ?
C5 C16 1.425(7) . ?
C6 C7 1.384(8) . ?
C7 C8 1.379(10) . ?
C8 C9 1.384(8) . ?
C9 C10 1.432(7) . ?
C9 C16 1.436(6) . ?
C10 C11 1.345(8) . ?
C11 C12 1.434(6) . ?
C12 C13 1.395(7) . ?
C12 C15 1.422(6) . ?
C13 C14 1.386(7) . ?
C15 C16 1.418(7) . ?
O2 C21 1.379(5) . ?
C21 C22 1.403(7) . ?
C21 C34 1.380(6) . ?
C22 C23 1.436(6) . ?
C22 C35 1.417(6) . ?
C23 C24 1.356(7) . ?
C24 C25 1.417(7) . ?
C25 C26 1.418(7) . ?
C25 C36 1.424(7) . ?
C26 C27 1.374(8) . ?
C27 C28 1.391(8) . ?
C28 C29 1.385(8) . ?
C29 C30 1.452(8) . ?
C29 C36 1.428(6) . ?
C30 C31 1.334(8) . ?
C31 C32 1.435(6) . ?
C32 C33 1.392(7) . ?
C32 C35 1.423(6) . ?
C33 C34 1.397(7) . ?
C35 C36 1.420(7) . ?

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 C1 C2 116.5(4) . . ?
C14 C1 O1 122.0(4) . . ?
C14 C1 C2 121.3(4) . . ?
C1 C2 C3 121.5(4) . . ?
C1 C2 C15 119.0(4) . . ?
C15 C2 C3 119.5(4) . . ?
C4 C3 C2 119.8(4) . . ?
C3 C4 C5 122.0(4) . . ?
C4 C5 C16 118.7(4) . . ?
C6 C5 C4 123.1(5) . . ?
C6 C5 C16 118.2(4) . . ?
C7 C6 C5 120.9(6) . . ?
C8 C7 C6 121.2(6) . . ?
C7 C8 C9 120.6(5) . . ?
C8 C9 C10 123.1(5) . . ?
C8 C9 C16 119.3(5) . . ?
C10 C9 C16 117.6(4) . . ?
C11 C10 C9 122.3(4) . . ?
C10 C11 C12 121.4(5) . . ?
C13 C12 C11 122.5(4) . . ?
C13 C12 C15 119.2(4) . . ?
C15 C12 C11 118.3(5) . . ?
C14 C13 C12 120.8(4) . . ?
C13 C14 C1 120.0(5) . . ?
C2 C15 C12 119.7(4) . . ?
C2 C15 C16 120.0(4) . . ?
C16 C15 C12 120.3(4) . . ?
C5 C16 C9 119.7(5) . . ?
C15 C16 C5 120.1(4) . . ?
C15 C16 C9 120.2(4) . . ?
O2 C21 C22 116.7(4) . . ?
O2 C21 C34 121.1(4) . . ?
C34 C21 C22 122.0(4) . . ?
C21 C22 C23 122.8(4) . . ?
C21 C22 C35 118.1(4) . . ?
C35 C22 C23 119.0(4) . . ?
C24 C23 C22 120.6(4) . . ?
C23 C24 C25 121.9(4) . . ?
C24 C25 C26 123.0(5) . . ?
C24 C25 C36 118.6(4) . . ?
C26 C25 C36 118.3(4) . . ?
C27 C26 C25 120.7(5) . . ?
C26 C27 C28 121.4(5) . . ?
C29 C28 C27 120.0(5) . . ?
C28 C29 C30 122.4(5) . . ?
C28 C29 C36 120.2(5) . . ?
C36 C29 C30 117.5(5) . . ?
C31 C30 C29 121.5(4) . . ?
C30 C31 C32 122.4(5) . . ?
C33 C32 C31 122.7(4) . . ?
C33 C32 C35 119.4(4) . . ?
C35 C32 C31 117.9(5) . . ?
C32 C33 C34 120.6(4) . . ?
C21 C34 C33 119.7(4) . . ?
C22 C35 C32 120.0(4) . . ?
C22 C35 C36 119.7(4) . . ?
C36 C35 C32 120.3(4) . . ?
C25 C36 C29 119.4(5) . . ?
C35 C36 C25 120.1(4) . . ?
C35 C36 C29 120.5(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.543(3)
2 0.457(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_t220
_database_code_depnum_ccdc_archive 'CCDC 1892302'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8211(6)
_cell_length_b                   4.55654(16)
_cell_length_c                   16.6176(6)
_cell_angle_alpha                90
_cell_angle_beta                 89.991(4)
_cell_angle_gamma                90
_cell_volume                     1046.52(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3718
_cell_measurement_temperature    219.98(10)
_cell_measurement_theta_max      75.5380
_cell_measurement_theta_min      4.1370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6212
_diffrn_reflns_point_group_measured_fraction_full 0.848
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.039
_diffrn_reflns_theta_min         2.659
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      219.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1011701000
_diffrn_orient_matrix_UB_12      -0.1411355000
_diffrn_orient_matrix_UB_13      0.0036954000
_diffrn_orient_matrix_UB_21      0.0003112000
_diffrn_orient_matrix_UB_22      -0.0306762000
_diffrn_orient_matrix_UB_23      -0.0923562000
_diffrn_orient_matrix_UB_31      0.0467953000
_diffrn_orient_matrix_UB_32      0.3055691000
_diffrn_orient_matrix_UB_33      -0.0075113000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.521
_reflns_Friedel_fraction_full    0.673
_reflns_Friedel_fraction_max     0.684
_reflns_number_gt                2911
_reflns_number_total             3036
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.544(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.060
_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)+(0.0896P)²+0.0564P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.456(3)
 0.544(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6420(2) 0.7255(9) 0.42721(19) 0.0398(7) Uani 1 1 d D . . . .
C1 C 0.7179(3) 0.6836(11) 0.4810(3) 0.0305(10) Uani 1 1 d . . . . .
C2 C 0.7017(3) 0.4872(11) 0.5435(3) 0.0270(9) Uani 1 1 d . . . . .
C3 C 0.6084(3) 0.3468(11) 0.5547(3) 0.0321(11) Uani 1 1 d . . . . .
H3 H 0.5577 0.3866 0.5196 0.039 Uiso 1 1 calc R . . . .
C4 C 0.5956(3) 0.1573(12) 0.6167(3) 0.0363(11) Uani 1 1 d . . . . .
H4 H 0.5352 0.0712 0.6237 0.044 Uiso 1 1 calc R . . . .
C5 C 0.6716(4) 0.0845(11) 0.6719(3) 0.0341(10) Uani 1 1 d . . . . .
C6 C 0.6594(4) -0.1105(14) 0.7362(3) 0.0475(13) Uani 1 1 d . . . . .
H6 H 0.6000 -0.2021 0.7438 0.057 Uiso 1 1 calc R . . . .
C7 C 0.7348(6) -0.1685(16) 0.7885(3) 0.0585(17) Uani 1 1 d . . . . .
H7 H 0.7256 -0.3010 0.8304 0.070 Uiso 1 1 calc R . . . .
C8 C 0.8231(5) -0.0335(15) 0.7797(3) 0.0552(16) Uani 1 1 d . . . . .
H8 H 0.8720 -0.0712 0.8167 0.066 Uiso 1 1 calc R . . . .
C9 C 0.8404(4) 0.1580(12) 0.7166(3) 0.0413(12) Uani 1 1 d . . . . .
C10 C 0.9312(4) 0.3022(14) 0.7035(3) 0.0469(14) Uani 1 1 d . . . . .
H10 H 0.9818 0.2660 0.7389 0.056 Uiso 1 1 calc R . . . .
C11 C 0.9459(4) 0.4877(14) 0.6418(3) 0.0443(13) Uani 1 1 d . . . . .
H11 H 1.0065 0.5727 0.6352 0.053 Uiso 1 1 calc R . . . .
C12 C 0.8701(3) 0.5575(11) 0.5861(3) 0.0331(10) Uani 1 1 d . . . . .
C13 C 0.8823(3) 0.7549(13) 0.5231(3) 0.0381(11) Uani 1 1 d . . . . .
H13 H 0.9418 0.8465 0.5161 0.046 Uiso 1 1 calc R . . . .
C14 C 0.8074(3) 0.8172(12) 0.4706(3) 0.0374(11) Uani 1 1 d . . . . .
H14 H 0.8169 0.9483 0.4284 0.045 Uiso 1 1 calc R . . . .
C15 C 0.7781(3) 0.4214(11) 0.5969(2) 0.0265(9) Uani 1 1 d . . . . .
C16 C 0.7626(3) 0.2245(13) 0.6621(3) 0.0319(10) Uani 1 1 d . . . . .
O2 O 0.3693(3) 0.7272(9) 0.66472(19) 0.0416(8) Uani 1 1 d D . . . .
C21 C 0.2999(3) 0.6756(11) 0.7224(3) 0.0321(10) Uani 1 1 d . . . . .
C22 C 0.3241(3) 0.4731(11) 0.7830(3) 0.0297(10) Uani 1 1 d . . . . .
C23 C 0.4187(3) 0.3459(12) 0.7904(3) 0.0340(10) Uani 1 1 d . . . . .
H23 H 0.4668 0.3949 0.7536 0.041 Uiso 1 1 calc R . . . .
C24 C 0.4384(3) 0.1551(12) 0.8505(3) 0.0390(12) Uani 1 1 d . . . . .
H24 H 0.5003 0.0763 0.8543 0.047 Uiso 1 1 calc R . . . .
C25 C 0.3678(4) 0.0712(11) 0.9080(3) 0.0352(10) Uani 1 1 d . . . . .
C26 C 0.3869(4) -0.1300(14) 0.9712(3) 0.0455(13) Uani 1 1 d . . . . .
H26 H 0.4480 -0.2141 0.9760 0.055 Uiso 1 1 calc R . . . .
C27 C 0.3153(5) -0.2011(14) 1.0255(3) 0.0507(15) Uani 1 1 d . . . . .
H27 H 0.3294 -0.3306 1.0671 0.061 Uiso 1 1 calc R . . . .
C28 C 0.2231(5) -0.0853(13) 1.0198(3) 0.0458(13) Uani 1 1 d . . . . .
H28 H 0.1759 -0.1411 1.0566 0.055 Uiso 1 1 calc R . . . .
C29 C 0.2007(4) 0.1137(13) 0.9594(3) 0.0394(12) Uani 1 1 d . . . . .
C30 C 0.1060(4) 0.2411(16) 0.9501(3) 0.0469(13) Uani 1 1 d . . . . .
H30 H 0.0570 0.1868 0.9854 0.056 Uiso 1 1 calc R . . . .
C31 C 0.0865(3) 0.4351(15) 0.8920(3) 0.0461(14) Uani 1 1 d . . . . .
H31 H 0.0248 0.5153 0.8890 0.055 Uiso 1 1 calc R . . . .
C32 C 0.1577(3) 0.5232(11) 0.8345(3) 0.0331(10) Uani 1 1 d . . . . .
C33 C 0.1386(3) 0.7277(12) 0.7742(3) 0.0379(10) Uani 1 1 d . . . . .
H33 H 0.0780 0.8157 0.7715 0.045 Uiso 1 1 calc R . . . .
C34 C 0.2094(3) 0.8021(12) 0.7177(3) 0.0360(11) Uani 1 1 d . . . . .
H34 H 0.1956 0.9364 0.6772 0.043 Uiso 1 1 calc R . . . .
C35 C 0.2520(3) 0.3999(11) 0.8405(2) 0.0273(9) Uani 1 1 d . . . . .
C36 C 0.2733(3) 0.1965(12) 0.9021(3) 0.0308(10) Uani 1 1 d . . . . .
H1 H 0.649(4) 0.896(7) 0.412(3) 0.041(15) Uiso 1 1 d D . . . .
H2 H 0.363(6) 0.885(11) 0.639(4) 0.10(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.391(5) . ?
C1 C2 1.390(7) . ?
C1 C14 1.389(7) . ?
C2 C3 1.451(6) . ?
C2 C15 1.412(5) . ?
C3 C4 1.355(7) . ?
C4 C5 1.433(7) . ?
C5 C6 1.400(7) . ?
C5 C16 1.420(7) . ?
C6 C7 1.382(9) . ?
C7 C8 1.375(11) . ?
C8 C9 1.385(9) . ?
C9 C10 1.433(8) . ?
C9 C16 1.438(6) . ?
C10 C11 1.343(8) . ?
C11 C12 1.434(7) . ?
C12 C13 1.391(8) . ?
C12 C15 1.426(6) . ?
C13 C14 1.384(7) . ?
C15 C16 1.423(7) . ?
O2 C21 1.377(5) . ?
C21 C22 1.405(7) . ?
C21 C34 1.379(7) . ?
C22 C23 1.436(6) . ?
C22 C35 1.421(6) . ?
C23 C24 1.353(7) . ?
C24 C25 1.418(7) . ?
C25 C26 1.418(8) . ?
C25 C36 1.429(7) . ?
C26 C27 1.378(8) . ?
C27 C28 1.383(9) . ?
C28 C29 1.387(8) . ?
C29 C30 1.441(8) . ?
C29 C36 1.434(6) . ?
C30 C31 1.335(9) . ?
C31 C32 1.430(7) . ?
C32 C33 1.394(7) . ?
C32 C35 1.422(6) . ?
C33 C34 1.397(7) . ?
C35 C36 1.413(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 116.6(4) . . ?
C14 C1 O1 122.1(4) . . ?
C14 C1 C2 121.2(4) . . ?
C1 C2 C3 121.5(4) . . ?
C1 C2 C15 119.1(4) . . ?
C15 C2 C3 119.3(4) . . ?
C4 C3 C2 119.6(4) . . ?
C3 C4 C5 122.6(5) . . ?
C6 C5 C4 123.2(5) . . ?
C6 C5 C16 118.6(5) . . ?
C16 C5 C4 118.1(4) . . ?
C7 C6 C5 120.7(6) . . ?
C8 C7 C6 121.1(6) . . ?
C7 C8 C9 121.0(6) . . ?
C8 C9 C10 123.7(5) . . ?
C8 C9 C16 118.7(5) . . ?
C10 C9 C16 117.5(5) . . ?
C11 C10 C9 122.5(4) . . ?
C10 C11 C12 121.5(5) . . ?
C13 C12 C11 122.8(5) . . ?
C13 C12 C15 119.0(4) . . ?
C15 C12 C11 118.2(5) . . ?
C14 C13 C12 121.1(4) . . ?
C13 C14 C1 119.9(5) . . ?
C2 C15 C12 119.7(4) . . ?
C2 C15 C16 120.0(4) . . ?
C16 C15 C12 120.3(4) . . ?
C5 C16 C9 119.7(5) . . ?
C5 C16 C15 120.2(4) . . ?
C15 C16 C9 120.0(4) . . ?
O2 C21 C22 116.4(4) . . ?
O2 C21 C34 121.4(4) . . ?
C34 C21 C22 122.0(4) . . ?
C21 C22 C23 122.9(4) . . ?
C21 C22 C35 118.0(4) . . ?
C35 C22 C23 119.1(4) . . ?
C24 C23 C22 120.4(4) . . ?
C23 C24 C25 122.2(5) . . ?
C24 C25 C26 123.0(5) . . ?
C24 C25 C36 118.3(4) . . ?
C26 C25 C36 118.6(5) . . ?
C27 C26 C25 120.2(6) . . ?
C26 C27 C28 121.8(6) . . ?
C27 C28 C29 120.3(5) . . ?
C28 C29 C30 123.0(5) . . ?
C28 C29 C36 119.7(5) . . ?
C36 C29 C30 117.3(5) . . ?
C31 C30 C29 121.9(5) . . ?
C30 C31 C32 122.0(5) . . ?
C33 C32 C31 122.6(5) . . ?
C33 C32 C35 119.2(4) . . ?
C35 C32 C31 118.2(5) . . ?
C32 C33 C34 120.8(4) . . ?
C21 C34 C33 119.7(5) . . ?
C22 C35 C32 120.2(4) . . ?
C36 C35 C22 119.7(4) . . ?
C36 C35 C32 120.1(4) . . ?
C25 C36 C29 119.3(5) . . ?
C35 C36 C25 120.2(4) . . ?
C35 C36 C29 120.5(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.456(3)
2 0.544(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_t150
_database_code_depnum_ccdc_archive 'CCDC 1892294'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7768(5)
_cell_length_b                   4.53799(13)
_cell_length_c                   16.5780(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.980(3)
_cell_angle_gamma                90
_cell_volume                     1036.44(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4146
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      75.4560
_cell_measurement_theta_min      4.1440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6104
_diffrn_reflns_point_group_measured_fraction_full 0.841
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.856
_diffrn_reflns_theta_min         2.665
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1015342000
_diffrn_orient_matrix_UB_12      -0.1407621000
_diffrn_orient_matrix_UB_13      -0.0044708000
_diffrn_orient_matrix_UB_21      -0.0010215000
_diffrn_orient_matrix_UB_22      -0.0330036000
_diffrn_orient_matrix_UB_23      0.0925459000
_diffrn_orient_matrix_UB_31      -0.0467092000
_diffrn_orient_matrix_UB_32      0.3071153000
_diffrn_orient_matrix_UB_33      0.0078336000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.509
_reflns_Friedel_fraction_full    0.657
_reflns_Friedel_fraction_max     0.671
_reflns_number_gt                2931
_reflns_number_total             2994
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.547(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2994
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.047
_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)+(0.0988P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1285
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.453(3)
 0.547(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6410(2) 0.7283(8) 0.42708(17) 0.0283(7) Uani 1 1 d D . . . .
C1 C 0.7175(3) 0.6873(11) 0.4806(2) 0.0223(9) Uani 1 1 d . . . . .
C2 C 0.7009(3) 0.4895(10) 0.5432(2) 0.0198(9) Uani 1 1 d . . . . .
C3 C 0.6080(3) 0.3480(11) 0.5550(2) 0.0231(9) Uani 1 1 d . . . . .
H3 H 0.5569 0.3881 0.5200 0.028 Uiso 1 1 calc R . . . .
C4 C 0.5952(3) 0.1558(11) 0.6173(3) 0.0264(10) Uani 1 1 d . . . . .
H4 H 0.5347 0.0683 0.6243 0.032 Uiso 1 1 calc R . . . .
C5 C 0.6714(3) 0.0846(10) 0.6720(2) 0.0251(9) Uani 1 1 d . . . . .
C6 C 0.6599(4) -0.1124(13) 0.7365(3) 0.0348(11) Uani 1 1 d . . . . .
H6 H 0.6005 -0.2053 0.7441 0.042 Uiso 1 1 calc R . . . .
C7 C 0.7358(5) -0.1708(14) 0.7891(3) 0.0416(13) Uani 1 1 d . . . . .
H7 H 0.7269 -0.3042 0.8310 0.050 Uiso 1 1 calc R . . . .
C8 C 0.8251(4) -0.0315(13) 0.7797(3) 0.0399(13) Uani 1 1 d . . . . .
H8 H 0.8744 -0.0665 0.8168 0.048 Uiso 1 1 calc R . . . .
C9 C 0.8413(3) 0.1572(11) 0.7163(3) 0.0293(10) Uani 1 1 d . . . . .
C10 C 0.9327(3) 0.3027(12) 0.7032(3) 0.0314(11) Uani 1 1 d . . . . .
H10 H 0.9837 0.2662 0.7385 0.038 Uiso 1 1 calc R . . . .
C11 C 0.9469(3) 0.4899(12) 0.6412(3) 0.0301(11) Uani 1 1 d . . . . .
H11 H 1.0076 0.5756 0.6342 0.036 Uiso 1 1 calc R . . . .
C12 C 0.8702(3) 0.5601(10) 0.5857(2) 0.0237(9) Uani 1 1 d . . . . .
C13 C 0.8825(3) 0.7581(11) 0.5226(3) 0.0263(9) Uani 1 1 d . . . . .
H13 H 0.9422 0.8505 0.5157 0.032 Uiso 1 1 calc R . . . .
C14 C 0.8070(3) 0.8203(11) 0.4696(3) 0.0257(10) Uani 1 1 d . . . . .
H14 H 0.8166 0.9505 0.4271 0.031 Uiso 1 1 calc R . . . .
C15 C 0.7782(3) 0.4227(11) 0.5965(2) 0.0190(9) Uani 1 1 d . . . . .
C16 C 0.7630(3) 0.2265(12) 0.6619(2) 0.0234(9) Uani 1 1 d . . . . .
O2 O 0.3699(2) 0.7305(8) 0.66475(17) 0.0296(7) Uani 1 1 d D . . . .
C21 C 0.3005(3) 0.6772(10) 0.7224(2) 0.0215(9) Uani 1 1 d . . . . .
C22 C 0.3238(3) 0.4730(10) 0.7834(3) 0.0205(9) Uani 1 1 d . . . . .
C23 C 0.4193(3) 0.3448(11) 0.7909(3) 0.0238(10) Uani 1 1 d . . . . .
H23 H 0.4676 0.3941 0.7540 0.029 Uiso 1 1 calc R . . . .
C24 C 0.4390(3) 0.1541(10) 0.8511(3) 0.0281(10) Uani 1 1 d . . . . .
H24 H 0.5012 0.0756 0.8551 0.034 Uiso 1 1 calc R . . . .
C25 C 0.3682(3) 0.0695(10) 0.9085(3) 0.0241(9) Uani 1 1 d . . . . .
C26 C 0.3868(4) -0.1326(12) 0.9720(3) 0.0313(10) Uani 1 1 d . . . . .
H26 H 0.4483 -0.2149 0.9770 0.038 Uiso 1 1 calc R . . . .
C27 C 0.3158(4) -0.2088(12) 1.0261(3) 0.0345(11) Uani 1 1 d . . . . .
H27 H 0.3299 -0.3401 1.0675 0.041 Uiso 1 1 calc R . . . .
C28 C 0.2224(4) -0.0914(12) 1.0197(3) 0.0312(10) Uani 1 1 d . . . . .
H28 H 0.1745 -0.1481 1.0561 0.037 Uiso 1 1 calc R . . . .
C29 C 0.2008(3) 0.1096(11) 0.9592(2) 0.0268(10) Uani 1 1 d . . . . .
C30 C 0.1048(3) 0.2372(14) 0.9500(3) 0.0332(11) Uani 1 1 d . . . . .
H30 H 0.0558 0.1826 0.9856 0.040 Uiso 1 1 calc R . . . .
C31 C 0.0852(3) 0.4312(13) 0.8917(3) 0.0317(11) Uani 1 1 d . . . . .
H31 H 0.0231 0.5106 0.8881 0.038 Uiso 1 1 calc R . . . .
C32 C 0.1574(3) 0.5201(11) 0.8345(3) 0.0239(9) Uani 1 1 d . . . . .
C33 C 0.1379(3) 0.7282(11) 0.7740(2) 0.0259(9) Uani 1 1 d . . . . .
H33 H 0.0771 0.8163 0.7713 0.031 Uiso 1 1 calc R . . . .
C34 C 0.2095(3) 0.8043(11) 0.7176(3) 0.0257(9) Uani 1 1 d . . . . .
H34 H 0.1958 0.9398 0.6771 0.031 Uiso 1 1 calc R . . . .
C35 C 0.2519(3) 0.3995(10) 0.8405(2) 0.0172(8) Uani 1 1 d . . . . .
C36 C 0.2729(3) 0.1934(11) 0.9022(2) 0.0223(9) Uani 1 1 d . . . . .
H1 H 0.648(3) 0.897(6) 0.408(2) 0.017(11) Uiso 1 1 d D . . . .
H2 H 0.361(5) 0.887(9) 0.639(4) 0.06(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.390(5) . ?
C1 C2 1.391(6) . ?
C1 C14 1.385(6) . ?
C2 C3 1.446(6) . ?
C2 C15 1.415(5) . ?
C3 C4 1.363(6) . ?
C4 C5 1.425(6) . ?
C5 C6 1.402(7) . ?
C5 C16 1.426(6) . ?
C6 C7 1.386(7) . ?
C7 C8 1.392(9) . ?
C8 C9 1.374(7) . ?
C9 C10 1.439(7) . ?
C9 C16 1.441(6) . ?
C10 C11 1.347(7) . ?
C11 C12 1.437(6) . ?
C12 C13 1.389(7) . ?
C12 C15 1.424(6) . ?
C13 C14 1.390(6) . ?
C15 C16 1.418(6) . ?
O2 C21 1.373(5) . ?
C21 C22 1.408(7) . ?
C21 C34 1.383(6) . ?
C22 C23 1.444(6) . ?
C22 C35 1.411(6) . ?
C23 C24 1.349(7) . ?
C24 C25 1.415(6) . ?
C25 C26 1.420(7) . ?
C25 C36 1.431(6) . ?
C26 C27 1.371(7) . ?
C27 C28 1.396(8) . ?
C28 C29 1.388(7) . ?
C29 C30 1.451(7) . ?
C29 C36 1.422(6) . ?
C30 C31 1.336(8) . ?
C31 C32 1.432(6) . ?
C32 C33 1.404(6) . ?
C32 C35 1.415(5) . ?
C33 C34 1.401(6) . ?
C35 C36 1.417(6) . ?

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 C1 C2 116.0(4) . . ?
C14 C1 O1 122.2(4) . . ?
C14 C1 C2 121.6(4) . . ?
C1 C2 C3 122.1(4) . . ?
C1 C2 C15 118.7(4) . . ?
C15 C2 C3 119.1(4) . . ?
C4 C3 C2 120.0(4) . . ?
C3 C4 C5 122.2(4) . . ?
C4 C5 C16 118.3(4) . . ?
C6 C5 C4 123.2(4) . . ?
C6 C5 C16 118.5(4) . . ?
C7 C6 C5 121.1(5) . . ?
C6 C7 C8 120.6(5) . . ?
C9 C8 C7 120.8(5) . . ?
C8 C9 C10 122.9(4) . . ?
C8 C9 C16 119.6(5) . . ?
C10 C9 C16 117.4(4) . . ?
C11 C10 C9 122.1(4) . . ?
C10 C11 C12 121.4(4) . . ?
C13 C12 C11 122.4(4) . . ?
C13 C12 C15 119.0(4) . . ?
C15 C12 C11 118.5(4) . . ?
C12 C13 C14 121.1(4) . . ?
C1 C14 C13 119.7(4) . . ?
C2 C15 C12 119.9(4) . . ?
C2 C15 C16 120.0(4) . . ?
C16 C15 C12 120.1(4) . . ?
C5 C16 C9 119.3(4) . . ?
C15 C16 C5 120.3(3) . . ?
C15 C16 C9 120.3(4) . . ?
O2 C21 C22 117.2(4) . . ?
O2 C21 C34 121.2(4) . . ?
C34 C21 C22 121.5(4) . . ?
C21 C22 C23 122.4(4) . . ?
C21 C22 C35 118.5(4) . . ?
C35 C22 C23 119.1(4) . . ?
C24 C23 C22 120.4(4) . . ?
C23 C24 C25 122.2(4) . . ?
C24 C25 C26 123.3(4) . . ?
C24 C25 C36 118.5(4) . . ?
C26 C25 C36 118.3(4) . . ?
C27 C26 C25 121.2(5) . . ?
C26 C27 C28 120.8(5) . . ?
C29 C28 C27 120.2(5) . . ?
C28 C29 C30 122.2(4) . . ?
C28 C29 C36 120.4(5) . . ?
C36 C29 C30 117.4(4) . . ?
C31 C30 C29 121.5(4) . . ?
C30 C31 C32 121.6(4) . . ?
C33 C32 C31 122.0(4) . . ?
C33 C32 C35 119.1(4) . . ?
C35 C32 C31 118.9(4) . . ?
C34 C33 C32 120.5(4) . . ?
C21 C34 C33 119.8(4) . . ?
C22 C35 C32 120.5(4) . . ?
C22 C35 C36 119.8(4) . . ?
C32 C35 C36 119.7(4) . . ?
C29 C36 C25 119.2(4) . . ?
C35 C36 C25 120.0(4) . . ?
C35 C36 C29 120.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.453(3)
2 0.547(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_t270
_database_code_depnum_ccdc_archive 'CCDC 1892306'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8490(6)
_cell_length_b                   4.57028(16)
_cell_length_c                   16.6432(6)
_cell_angle_alpha                90
_cell_angle_beta                 89.994(4)
_cell_angle_gamma                90
_cell_volume                     1053.41(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3150
_cell_measurement_temperature    270.02(10)
_cell_measurement_theta_max      74.2270
_cell_measurement_theta_min      4.1240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6249
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.024
_diffrn_reflns_theta_min         2.655
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      270.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1010326000
_diffrn_orient_matrix_UB_12      -0.1399691000
_diffrn_orient_matrix_UB_13      0.0044288000
_diffrn_orient_matrix_UB_21      0.0012238000
_diffrn_orient_matrix_UB_22      -0.0310498000
_diffrn_orient_matrix_UB_23      -0.0921824000
_diffrn_orient_matrix_UB_31      0.0465071000
_diffrn_orient_matrix_UB_32      0.3050648000
_diffrn_orient_matrix_UB_33      -0.0072700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.521
_reflns_Friedel_fraction_full    0.676
_reflns_Friedel_fraction_max     0.684
_reflns_number_gt                2777
_reflns_number_total             3057
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.544(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.037
_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)+(0.0939P)²+0.1515P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1489
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.456(4)
 0.544(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6430(3) 0.7237(11) 0.4275(2) 0.0499(10) Uani 1 1 d D . . . .
C1 C 0.7182(4) 0.6815(14) 0.4815(3) 0.0384(12) Uani 1 1 d . . . . .
C2 C 0.7022(4) 0.4857(13) 0.5439(3) 0.0338(11) Uani 1 1 d . . . . .
C3 C 0.6091(4) 0.3460(15) 0.5547(3) 0.0413(14) Uani 1 1 d . . . . .
H3 H 0.5587 0.3859 0.5195 0.050 Uiso 1 1 calc R . . . .
C4 C 0.5960(4) 0.1566(15) 0.6166(4) 0.0444(14) Uani 1 1 d . . . . .
H4 H 0.5358 0.0699 0.6231 0.053 Uiso 1 1 calc R . . . .
C5 C 0.6710(5) 0.0851(14) 0.6720(3) 0.0432(13) Uani 1 1 d . . . . .
C6 C 0.6589(6) -0.1100(17) 0.7358(4) 0.0586(17) Uani 1 1 d . . . . .
H6 H 0.6000 -0.2041 0.7429 0.070 Uiso 1 1 calc R . . . .
C7 C 0.7344(7) -0.165(2) 0.7889(4) 0.073(2) Uani 1 1 d . . . . .
H7 H 0.7250 -0.2938 0.8313 0.087 Uiso 1 1 calc R . . . .
C8 C 0.8220(7) -0.032(2) 0.7798(4) 0.071(2) Uani 1 1 d . . . . .
H8 H 0.8710 -0.0713 0.8164 0.085 Uiso 1 1 calc R . . . .
C9 C 0.8392(5) 0.1584(15) 0.7168(3) 0.0498(16) Uani 1 1 d . . . . .
C10 C 0.9298(5) 0.2988(18) 0.7040(4) 0.0561(18) Uani 1 1 d . . . . .
H10 H 0.9804 0.2592 0.7391 0.067 Uiso 1 1 calc R . . . .
C11 C 0.9447(4) 0.4864(18) 0.6430(4) 0.0550(17) Uani 1 1 d . . . . .
H11 H 1.0050 0.5735 0.6374 0.066 Uiso 1 1 calc R . . . .
C12 C 0.8702(4) 0.5553(15) 0.5867(3) 0.0417(13) Uani 1 1 d . . . . .
C13 C 0.8818(4) 0.7514(16) 0.5237(4) 0.0478(15) Uani 1 1 d . . . . .
H13 H 0.9412 0.8429 0.5167 0.057 Uiso 1 1 calc R . . . .
C14 C 0.8074(4) 0.8140(15) 0.4713(4) 0.0470(15) Uani 1 1 d . . . . .
H14 H 0.8171 0.9447 0.4292 0.056 Uiso 1 1 calc R . . . .
C15 C 0.7783(4) 0.4207(14) 0.5971(3) 0.0347(12) Uani 1 1 d . . . . .
C16 C 0.7627(4) 0.2250(15) 0.6620(3) 0.0381(12) Uani 1 1 d . . . . .
O2 O 0.3688(3) 0.7262(12) 0.6647(2) 0.0521(10) Uani 1 1 d D . . . .
C21 C 0.3002(4) 0.6748(14) 0.7226(3) 0.0399(12) Uani 1 1 d . . . . .
C22 C 0.3238(4) 0.4734(13) 0.7830(3) 0.0367(12) Uani 1 1 d . . . . .
C23 C 0.4182(4) 0.3456(15) 0.7904(4) 0.0418(13) Uani 1 1 d . . . . .
H23 H 0.4660 0.3939 0.7535 0.050 Uiso 1 1 calc R . . . .
C24 C 0.4380(4) 0.1557(15) 0.8504(4) 0.0485(15) Uani 1 1 d . . . . .
H24 H 0.4998 0.0772 0.8542 0.058 Uiso 1 1 calc R . . . .
C25 C 0.3677(4) 0.0727(14) 0.9078(3) 0.0445(13) Uani 1 1 d . . . . .
C26 C 0.3870(5) -0.1279(18) 0.9708(4) 0.0565(17) Uani 1 1 d . . . . .
H26 H 0.4478 -0.2120 0.9754 0.068 Uiso 1 1 calc R . . . .
C27 C 0.3156(6) -0.1982(17) 1.0251(4) 0.0606(19) Uani 1 1 d . . . . .
H27 H 0.3294 -0.3279 1.0666 0.073 Uiso 1 1 calc R . . . .
C28 C 0.2242(6) -0.0805(18) 1.0194(4) 0.0595(19) Uani 1 1 d . . . . .
H28 H 0.1772 -0.1348 1.0564 0.071 Uiso 1 1 calc R . . . .
C29 C 0.2012(5) 0.1169(17) 0.9595(3) 0.0501(16) Uani 1 1 d . . . . .
C30 C 0.1073(4) 0.246(2) 0.9500(4) 0.0570(18) Uani 1 1 d . . . . .
H30 H 0.0587 0.1938 0.9859 0.068 Uiso 1 1 calc R . . . .
C31 C 0.0870(4) 0.4362(19) 0.8920(4) 0.0552(18) Uani 1 1 d . . . . .
H31 H 0.0251 0.5143 0.8887 0.066 Uiso 1 1 calc R . . . .
C32 C 0.1583(4) 0.5242(14) 0.8343(4) 0.0425(13) Uani 1 1 d . . . . .
C33 C 0.1393(4) 0.7271(17) 0.7740(3) 0.0485(13) Uani 1 1 d . . . . .
H33 H 0.0788 0.8143 0.7711 0.058 Uiso 1 1 calc R . . . .
C34 C 0.2098(4) 0.8013(15) 0.7179(4) 0.0454(14) Uani 1 1 d . . . . .
H34 H 0.1961 0.9354 0.6775 0.054 Uiso 1 1 calc R . . . .
C35 C 0.2519(4) 0.4003(14) 0.8405(3) 0.0351(12) Uani 1 1 d . . . . .
C36 C 0.2739(4) 0.1977(15) 0.9024(3) 0.0374(12) Uani 1 1 d . . . . .
H1 H 0.651(6) 0.888(9) 0.409(4) 0.07(3) Uiso 1 1 d D . . . .
H2 H 0.363(8) 0.868(15) 0.634(5) 0.13(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.388(6) . ?
C1 C2 1.388(8) . ?
C1 C14 1.386(8) . ?
C2 C3 1.450(7) . ?
C2 C15 1.409(7) . ?
C3 C4 1.358(8) . ?
C4 C5 1.426(8) . ?
C5 C6 1.397(8) . ?
C5 C16 1.432(8) . ?
C6 C7 1.391(11) . ?
C7 C8 1.364(13) . ?
C8 C9 1.384(11) . ?
C9 C10 1.424(10) . ?
C9 C16 1.431(8) . ?
C10 C11 1.345(10) . ?
C11 C12 1.429(8) . ?
C12 C13 1.388(9) . ?
C12 C15 1.424(7) . ?
C13 C14 1.381(9) . ?
C15 C16 1.419(8) . ?
O2 C21 1.374(6) . ?
C21 C22 1.402(9) . ?
C21 C34 1.381(8) . ?
C22 C23 1.437(8) . ?
C22 C35 1.421(7) . ?
C23 C24 1.352(9) . ?
C24 C25 1.415(8) . ?
C25 C26 1.418(9) . ?
C25 C36 1.422(9) . ?
C26 C27 1.377(10) . ?
C27 C28 1.379(11) . ?
C28 C29 1.382(10) . ?
C29 C30 1.436(10) . ?
C29 C36 1.433(8) . ?
C30 C31 1.330(11) . ?
C31 C32 1.435(8) . ?
C32 C33 1.392(9) . ?
C32 C35 1.418(8) . ?
C33 C34 1.392(9) . ?
C35 C36 1.418(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 117.0(5) . . ?
C14 C1 O1 121.9(5) . . ?
C14 C1 C2 121.0(5) . . ?
C1 C2 C3 121.2(5) . . ?
C1 C2 C15 119.1(5) . . ?
C15 C2 C3 119.6(5) . . ?
C4 C3 C2 119.6(5) . . ?
C3 C4 C5 122.6(6) . . ?
C4 C5 C16 118.0(5) . . ?
C6 C5 C4 123.4(6) . . ?
C6 C5 C16 118.6(6) . . ?
C7 C6 C5 120.5(7) . . ?
C8 C7 C6 121.3(8) . . ?
C7 C8 C9 121.1(7) . . ?
C8 C9 C10 123.3(6) . . ?
C8 C9 C16 119.3(7) . . ?
C10 C9 C16 117.5(6) . . ?
C11 C10 C9 122.4(6) . . ?
C10 C11 C12 121.7(6) . . ?
C13 C12 C11 123.7(6) . . ?
C13 C12 C15 118.3(5) . . ?
C15 C12 C11 118.0(6) . . ?
C14 C13 C12 121.7(5) . . ?
C13 C14 C1 119.8(6) . . ?
C2 C15 C12 120.1(5) . . ?
C2 C15 C16 119.8(5) . . ?
C16 C15 C12 120.1(5) . . ?
C9 C16 C5 119.3(6) . . ?
C15 C16 C5 120.3(5) . . ?
C15 C16 C9 120.4(5) . . ?
O2 C21 C22 117.0(5) . . ?
O2 C21 C34 121.0(5) . . ?
C34 C21 C22 121.8(5) . . ?
C21 C22 C23 122.7(5) . . ?
C21 C22 C35 118.3(5) . . ?
C35 C22 C23 119.0(5) . . ?
C24 C23 C22 120.6(5) . . ?
C23 C24 C25 122.1(6) . . ?
C24 C25 C26 122.9(6) . . ?
C24 C25 C36 118.6(5) . . ?
C26 C25 C36 118.6(6) . . ?
C27 C26 C25 120.1(7) . . ?
C26 C27 C28 121.5(7) . . ?
C27 C28 C29 121.1(7) . . ?
C28 C29 C30 123.8(6) . . ?
C28 C29 C36 119.0(7) . . ?
C36 C29 C30 117.3(6) . . ?
C31 C30 C29 122.7(6) . . ?
C30 C31 C32 121.6(6) . . ?
C33 C32 C31 122.6(6) . . ?
C33 C32 C35 119.4(5) . . ?
C35 C32 C31 117.9(6) . . ?
C34 C33 C32 120.9(6) . . ?
C21 C34 C33 119.7(6) . . ?
C32 C35 C22 119.8(5) . . ?
C32 C35 C36 120.7(5) . . ?
C36 C35 C22 119.5(5) . . ?
C25 C36 C29 119.8(6) . . ?
C35 C36 C25 120.3(5) . . ?
C35 C36 C29 119.9(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.456(4)
2 0.544(4)

####################################################################### 
# 
# 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_t230
_database_code_depnum_ccdc_archive 'CCDC 1892303'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8281(6)
_cell_length_b                   4.55914(15)
_cell_length_c                   16.6195(6)
_cell_angle_alpha                90
_cell_angle_beta                 89.994(4)
_cell_angle_gamma                90
_cell_volume                     1047.77(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3519
_cell_measurement_temperature    230.01(10)
_cell_measurement_theta_max      76.0700
_cell_measurement_theta_min      4.1340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6232
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         2.659
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      230.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1012194000
_diffrn_orient_matrix_UB_12      -0.1402015000
_diffrn_orient_matrix_UB_13      0.0044708000
_diffrn_orient_matrix_UB_21      0.0011820000
_diffrn_orient_matrix_UB_22      -0.0319757000
_diffrn_orient_matrix_UB_23      -0.0922963000
_diffrn_orient_matrix_UB_31      0.0465394000
_diffrn_orient_matrix_UB_32      0.3057066000
_diffrn_orient_matrix_UB_33      -0.0075279000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.516
_reflns_Friedel_fraction_full    0.667
_reflns_Friedel_fraction_max     0.677
_reflns_number_gt                2868
_reflns_number_total             3041
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.546(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.045
_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)+(0.0947P)²+0.1138P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1412
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.454(4)
 0.546(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6421(3) 0.7244(10) 0.4272(2) 0.0418(8) Uani 1 1 d D . . . .
C1 C 0.7178(4) 0.6827(13) 0.4812(3) 0.0341(11) Uani 1 1 d . . . . .
C2 C 0.7018(3) 0.4863(12) 0.5435(3) 0.0302(10) Uani 1 1 d . . . . .
C3 C 0.6088(3) 0.3460(13) 0.5549(3) 0.0349(12) Uani 1 1 d . . . . .
H3 H 0.5581 0.3854 0.5197 0.042 Uiso 1 1 calc R . . . .
C4 C 0.5957(4) 0.1574(13) 0.6169(3) 0.0391(12) Uani 1 1 d . . . . .
H4 H 0.5352 0.0719 0.6239 0.047 Uiso 1 1 calc R . . . .
C5 C 0.6712(4) 0.0851(12) 0.6720(3) 0.0371(11) Uani 1 1 d . . . . .
C6 C 0.6593(5) -0.1093(15) 0.7360(3) 0.0510(14) Uani 1 1 d . . . . .
H6 H 0.5999 -0.2015 0.7434 0.061 Uiso 1 1 calc R . . . .
C7 C 0.7345(6) -0.1672(18) 0.7888(3) 0.0614(19) Uani 1 1 d . . . . .
H7 H 0.7251 -0.2983 0.8309 0.074 Uiso 1 1 calc R . . . .
C8 C 0.8235(6) -0.0324(17) 0.7795(4) 0.0597(19) Uani 1 1 d . . . . .
H8 H 0.8726 -0.0709 0.8163 0.072 Uiso 1 1 calc R . . . .
C9 C 0.8404(4) 0.1586(13) 0.7165(3) 0.0435(13) Uani 1 1 d . . . . .
C10 C 0.9311(4) 0.2994(16) 0.7036(4) 0.0489(16) Uani 1 1 d . . . . .
H10 H 0.9819 0.2604 0.7386 0.059 Uiso 1 1 calc R . . . .
C11 C 0.9455(4) 0.4879(16) 0.6419(4) 0.0469(14) Uani 1 1 d . . . . .
H11 H 1.0059 0.5743 0.6355 0.056 Uiso 1 1 calc R . . . .
C12 C 0.8701(3) 0.5575(13) 0.5863(3) 0.0352(11) Uani 1 1 d . . . . .
C13 C 0.8821(4) 0.7547(14) 0.5231(3) 0.0412(13) Uani 1 1 d . . . . .
H13 H 0.9415 0.8471 0.5161 0.049 Uiso 1 1 calc R . . . .
C14 C 0.8070(4) 0.8157(14) 0.4704(3) 0.0398(12) Uani 1 1 d . . . . .
H14 H 0.8165 0.9454 0.4279 0.048 Uiso 1 1 calc R . . . .
C15 C 0.7785(3) 0.4218(13) 0.5969(3) 0.0298(11) Uani 1 1 d . . . . .
C16 C 0.7627(3) 0.2244(14) 0.6617(3) 0.0342(11) Uani 1 1 d . . . . .
O2 O 0.3691(3) 0.7272(10) 0.6649(2) 0.0444(9) Uani 1 1 d D . . . .
C21 C 0.3000(4) 0.6757(12) 0.7225(3) 0.0338(11) Uani 1 1 d . . . . .
C22 C 0.3239(4) 0.4736(12) 0.7830(3) 0.0315(11) Uani 1 1 d . . . . .
C23 C 0.4184(4) 0.3452(13) 0.7906(3) 0.0369(12) Uani 1 1 d . . . . .
H23 H 0.4664 0.3939 0.7537 0.044 Uiso 1 1 calc R . . . .
C24 C 0.4385(4) 0.1548(13) 0.8506(3) 0.0424(13) Uani 1 1 d . . . . .
H24 H 0.5003 0.0758 0.8543 0.051 Uiso 1 1 calc R . . . .
C25 C 0.3677(4) 0.0723(13) 0.9079(3) 0.0379(11) Uani 1 1 d . . . . .
C26 C 0.3872(5) -0.1286(16) 0.9710(3) 0.0479(14) Uani 1 1 d . . . . .
H26 H 0.4485 -0.2107 0.9759 0.057 Uiso 1 1 calc R . . . .
C27 C 0.3158(5) -0.2025(15) 1.0250(4) 0.0533(16) Uani 1 1 d . . . . .
H27 H 0.3296 -0.3346 1.0661 0.064 Uiso 1 1 calc R . . . .
C28 C 0.2235(5) -0.0840(15) 1.0195(3) 0.0484(15) Uani 1 1 d . . . . .
H28 H 0.1765 -0.1383 1.0566 0.058 Uiso 1 1 calc R . . . .
C29 C 0.2008(4) 0.1141(14) 0.9592(3) 0.0411(13) Uani 1 1 d . . . . .
C30 C 0.1061(4) 0.2425(18) 0.9503(4) 0.0501(15) Uani 1 1 d . . . . .
H30 H 0.0574 0.1893 0.9860 0.060 Uiso 1 1 calc R . . . .
C31 C 0.0865(4) 0.4352(17) 0.8923(3) 0.0478(15) Uani 1 1 d . . . . .
H31 H 0.0248 0.5151 0.8892 0.057 Uiso 1 1 calc R . . . .
C32 C 0.1579(4) 0.5231(13) 0.8345(3) 0.0363(11) Uani 1 1 d . . . . .
C33 C 0.1389(4) 0.7280(14) 0.7741(3) 0.0410(12) Uani 1 1 d . . . . .
H33 H 0.0783 0.8159 0.7713 0.049 Uiso 1 1 calc R . . . .
C34 C 0.2098(4) 0.8026(14) 0.7177(3) 0.0393(12) Uani 1 1 d . . . . .
H34 H 0.1961 0.9372 0.6773 0.047 Uiso 1 1 calc R . . . .
C35 C 0.2522(3) 0.3995(12) 0.8402(3) 0.0289(10) Uani 1 1 d . . . . .
C36 C 0.2733(3) 0.1970(14) 0.9022(3) 0.0328(11) Uani 1 1 d . . . . .
H1 H 0.648(4) 0.892(7) 0.409(3) 0.042(16) Uiso 1 1 d D . . . .
H2 H 0.360(7) 0.874(14) 0.635(5) 0.12(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.391(6) . ?
C1 C2 1.387(8) . ?
C1 C14 1.386(8) . ?
C2 C3 1.450(7) . ?
C2 C15 1.414(6) . ?
C3 C4 1.355(8) . ?
C4 C5 1.427(8) . ?
C5 C6 1.395(8) . ?
C5 C16 1.426(8) . ?
C6 C7 1.386(10) . ?
C7 C8 1.384(12) . ?
C8 C9 1.383(10) . ?
C9 C10 1.425(8) . ?
C9 C16 1.439(7) . ?
C10 C11 1.352(9) . ?
C11 C12 1.428(7) . ?
C12 C13 1.392(8) . ?
C12 C15 1.421(7) . ?
C13 C14 1.387(8) . ?
C15 C16 1.421(8) . ?
O2 C21 1.373(6) . ?
C21 C22 1.403(8) . ?
C21 C34 1.378(7) . ?
C22 C23 1.438(7) . ?
C22 C35 1.414(7) . ?
C23 C24 1.351(8) . ?
C24 C25 1.417(7) . ?
C25 C26 1.418(8) . ?
C25 C36 1.427(8) . ?
C26 C27 1.377(9) . ?
C27 C28 1.389(10) . ?
C28 C29 1.385(9) . ?
C29 C30 1.442(9) . ?
C29 C36 1.431(7) . ?
C30 C31 1.332(10) . ?
C31 C32 1.435(7) . ?
C32 C33 1.397(8) . ?
C32 C35 1.423(7) . ?
C33 C34 1.397(8) . ?
C35 C36 1.414(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 116.7(5) . . ?
C14 C1 O1 121.8(5) . . ?
C14 C1 C2 121.4(5) . . ?
C1 C2 C3 121.6(4) . . ?
C1 C2 C15 118.9(4) . . ?
C15 C2 C3 119.5(5) . . ?
C4 C3 C2 119.9(4) . . ?
C3 C4 C5 122.5(5) . . ?
C6 C5 C4 123.3(5) . . ?
C6 C5 C16 118.7(5) . . ?
C16 C5 C4 118.0(5) . . ?
C7 C6 C5 121.0(7) . . ?
C8 C7 C6 120.9(7) . . ?
C9 C8 C7 120.9(6) . . ?
C8 C9 C10 123.1(6) . . ?
C8 C9 C16 119.0(6) . . ?
C10 C9 C16 117.9(5) . . ?
C11 C10 C9 122.0(5) . . ?
C10 C11 C12 121.6(5) . . ?
C13 C12 C11 123.0(5) . . ?
C13 C12 C15 118.7(4) . . ?
C15 C12 C11 118.3(5) . . ?
C14 C13 C12 121.2(5) . . ?
C1 C14 C13 119.8(5) . . ?
C2 C15 C12 120.0(5) . . ?
C2 C15 C16 119.5(4) . . ?
C16 C15 C12 120.5(4) . . ?
C5 C16 C9 119.6(5) . . ?
C15 C16 C5 120.6(4) . . ?
C15 C16 C9 119.8(5) . . ?
O2 C21 C22 116.7(5) . . ?
O2 C21 C34 121.2(5) . . ?
C34 C21 C22 122.0(5) . . ?
C21 C22 C23 122.9(5) . . ?
C21 C22 C35 118.3(5) . . ?
C35 C22 C23 118.7(5) . . ?
C24 C23 C22 120.9(5) . . ?
C23 C24 C25 121.7(5) . . ?
C24 C25 C26 122.5(5) . . ?
C24 C25 C36 118.7(5) . . ?
C26 C25 C36 118.8(5) . . ?
C27 C26 C25 120.2(6) . . ?
C26 C27 C28 121.4(6) . . ?
C29 C28 C27 120.7(6) . . ?
C28 C29 C30 123.0(5) . . ?
C28 C29 C36 119.5(6) . . ?
C36 C29 C30 117.5(5) . . ?
C31 C30 C29 121.8(5) . . ?
C30 C31 C32 121.9(5) . . ?
C33 C32 C31 122.6(5) . . ?
C33 C32 C35 119.0(5) . . ?
C35 C32 C31 118.4(5) . . ?
C32 C33 C34 120.8(5) . . ?
C21 C34 C33 119.6(5) . . ?
C22 C35 C32 120.2(5) . . ?
C22 C35 C36 120.1(4) . . ?
C36 C35 C32 119.7(5) . . ?
C25 C36 C29 119.4(5) . . ?
C35 C36 C25 119.9(5) . . ?
C35 C36 C29 120.7(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.454(4)
2 0.546(4)

####################################################################### 
# 
# 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_t250
_database_code_depnum_ccdc_archive 'CCDC 1892304'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8405(6)
_cell_length_b                   4.56458(16)
_cell_length_c                   16.6279(6)
_cell_angle_alpha                90
_cell_angle_beta                 89.994(4)
_cell_angle_gamma                90
_cell_volume                     1050.49(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3316
_cell_measurement_temperature    250.02(10)
_cell_measurement_theta_max      75.7520
_cell_measurement_theta_min      2.6570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6223
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         2.657
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1011210000
_diffrn_orient_matrix_UB_12      -0.1399765000
_diffrn_orient_matrix_UB_13      -0.0043959000
_diffrn_orient_matrix_UB_21      -0.0011541000
_diffrn_orient_matrix_UB_22      -0.0313739000
_diffrn_orient_matrix_UB_23      0.0922655000
_diffrn_orient_matrix_UB_31      -0.0464936000
_diffrn_orient_matrix_UB_32      0.3054534000
_diffrn_orient_matrix_UB_33      0.0073874000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.519
_reflns_Friedel_fraction_full    0.674
_reflns_Friedel_fraction_max     0.681
_reflns_number_gt                2817
_reflns_number_total             3050
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.545(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3050
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.065
_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)+(0.1000P)²+0.0268P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1455
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.455(4)
 0.545(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6423(3) 0.7246(10) 0.4275(2) 0.0454(8) Uani 1 1 d D . . . .
C1 C 0.7179(4) 0.6811(13) 0.4813(3) 0.0359(11) Uani 1 1 d . . . . .
C2 C 0.7019(3) 0.4869(12) 0.5435(3) 0.0323(10) Uani 1 1 d . . . . .
C3 C 0.6090(3) 0.3456(13) 0.5548(3) 0.0386(12) Uani 1 1 d . . . . .
H3 H 0.5585 0.3850 0.5196 0.046 Uiso 1 1 calc R . . . .
C4 C 0.5958(4) 0.1556(14) 0.6168(3) 0.0436(13) Uani 1 1 d . . . . .
H4 H 0.5355 0.0691 0.6235 0.052 Uiso 1 1 calc R . . . .
C5 C 0.6715(4) 0.0843(13) 0.6718(3) 0.0399(11) Uani 1 1 d . . . . .
C6 C 0.6592(5) -0.1104(16) 0.7358(3) 0.0565(15) Uani 1 1 d . . . . .
H6 H 0.6000 -0.2028 0.7432 0.068 Uiso 1 1 calc R . . . .
C7 C 0.7349(7) -0.1673(18) 0.7886(4) 0.067(2) Uani 1 1 d . . . . .
H7 H 0.7258 -0.2985 0.8307 0.080 Uiso 1 1 calc R . . . .
C8 C 0.8227(6) -0.0328(17) 0.7794(4) 0.063(2) Uani 1 1 d . . . . .
H8 H 0.8718 -0.0713 0.8161 0.076 Uiso 1 1 calc R . . . .
C9 C 0.8399(4) 0.1587(14) 0.7168(3) 0.0465(14) Uani 1 1 d . . . . .
C10 C 0.9304(4) 0.3004(16) 0.7037(4) 0.0524(16) Uani 1 1 d . . . . .
H10 H 0.9811 0.2625 0.7388 0.063 Uiso 1 1 calc R . . . .
C11 C 0.9449(4) 0.4865(16) 0.6424(4) 0.0514(15) Uani 1 1 d . . . . .
H11 H 1.0054 0.5724 0.6362 0.062 Uiso 1 1 calc R . . . .
C12 C 0.8704(3) 0.5565(13) 0.5864(3) 0.0382(11) Uani 1 1 d . . . . .
C13 C 0.8820(4) 0.7539(14) 0.5235(4) 0.0445(13) Uani 1 1 d . . . . .
H13 H 0.9412 0.8470 0.5167 0.053 Uiso 1 1 calc R . . . .
C14 C 0.8075(4) 0.8147(14) 0.4708(4) 0.0436(13) Uani 1 1 d . . . . .
H14 H 0.8171 0.9446 0.4285 0.052 Uiso 1 1 calc R . . . .
C15 C 0.7783(3) 0.4216(13) 0.5967(3) 0.0317(11) Uani 1 1 d . . . . .
C16 C 0.7627(3) 0.2250(14) 0.6620(3) 0.0362(11) Uani 1 1 d . . . . .
O2 O 0.3691(3) 0.7267(10) 0.6647(2) 0.0481(9) Uani 1 1 d D . . . .
C21 C 0.3002(4) 0.6747(13) 0.7226(3) 0.0364(11) Uani 1 1 d . . . . .
C22 C 0.3237(4) 0.4736(12) 0.7829(3) 0.0343(11) Uani 1 1 d . . . . .
C23 C 0.4183(4) 0.3459(13) 0.7904(3) 0.0389(12) Uani 1 1 d . . . . .
H23 H 0.4663 0.3950 0.7536 0.047 Uiso 1 1 calc R . . . .
C24 C 0.4381(4) 0.1545(13) 0.8506(3) 0.0452(13) Uani 1 1 d . . . . .
H24 H 0.4997 0.0742 0.8542 0.054 Uiso 1 1 calc R . . . .
C25 C 0.3676(4) 0.0739(13) 0.9080(3) 0.0405(11) Uani 1 1 d . . . . .
C26 C 0.3868(5) -0.1274(16) 0.9714(3) 0.0514(15) Uani 1 1 d . . . . .
H26 H 0.4481 -0.2092 0.9763 0.062 Uiso 1 1 calc R . . . .
C27 C 0.3160(5) -0.2014(15) 1.0251(4) 0.0564(17) Uani 1 1 d . . . . .
H27 H 0.3299 -0.3335 1.0661 0.068 Uiso 1 1 calc R . . . .
C28 C 0.2236(6) -0.0827(16) 1.0195(3) 0.0530(16) Uani 1 1 d . . . . .
H28 H 0.1766 -0.1366 1.0566 0.064 Uiso 1 1 calc R . . . .
C29 C 0.2009(4) 0.1161(15) 0.9589(3) 0.0455(14) Uani 1 1 d . . . . .
C30 C 0.1065(4) 0.2437(18) 0.9502(4) 0.0530(16) Uani 1 1 d . . . . .
H30 H 0.0580 0.1910 0.9861 0.064 Uiso 1 1 calc R . . . .
C31 C 0.0869(4) 0.4354(17) 0.8922(3) 0.0504(15) Uani 1 1 d . . . . .
H31 H 0.0251 0.5146 0.8892 0.061 Uiso 1 1 calc R . . . .
C32 C 0.1578(4) 0.5241(13) 0.8342(3) 0.0383(11) Uani 1 1 d . . . . .
C33 C 0.1389(4) 0.7280(15) 0.7742(3) 0.0438(12) Uani 1 1 d . . . . .
H33 H 0.0785 0.8167 0.7717 0.053 Uiso 1 1 calc R . . . .
C34 C 0.2094(4) 0.8016(13) 0.7177(3) 0.0417(12) Uani 1 1 d . . . . .
H34 H 0.1956 0.9350 0.6770 0.050 Uiso 1 1 calc R . . . .
C35 C 0.2520(3) 0.3999(12) 0.8405(3) 0.0325(10) Uani 1 1 d . . . . .
C36 C 0.2738(4) 0.1980(14) 0.9021(3) 0.0359(11) Uani 1 1 d . . . . .
H1 H 0.649(4) 0.888(8) 0.406(3) 0.047(17) Uiso 1 1 d D . . . .
H2 H 0.358(7) 0.870(14) 0.635(5) 0.12(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.390(6) . ?
C1 C2 1.381(8) . ?
C1 C14 1.392(8) . ?
C2 C3 1.451(7) . ?
C2 C15 1.410(6) . ?
C3 C4 1.359(8) . ?
C4 C5 1.430(8) . ?
C5 C6 1.396(8) . ?
C5 C16 1.426(8) . ?
C6 C7 1.391(10) . ?
C7 C8 1.370(12) . ?
C8 C9 1.380(10) . ?
C9 C10 1.427(9) . ?
C9 C16 1.436(7) . ?
C10 C11 1.342(9) . ?
C11 C12 1.425(8) . ?
C12 C13 1.390(9) . ?
C12 C15 1.427(7) . ?
C13 C14 1.380(8) . ?
C15 C16 1.425(8) . ?
O2 C21 1.377(6) . ?
C21 C22 1.398(8) . ?
C21 C34 1.385(7) . ?
C22 C23 1.438(7) . ?
C22 C35 1.419(7) . ?
C23 C24 1.357(8) . ?
C24 C25 1.414(8) . ?
C25 C26 1.424(8) . ?
C25 C36 1.419(8) . ?
C26 C27 1.369(9) . ?
C27 C28 1.392(10) . ?
C28 C29 1.392(9) . ?
C29 C30 1.438(9) . ?
C29 C36 1.432(7) . ?
C30 C31 1.331(10) . ?
C31 C32 1.433(8) . ?
C32 C33 1.389(8) . ?
C32 C35 1.426(7) . ?
C33 C34 1.396(8) . ?
C35 C36 1.411(8) . ?

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 C1 C14 121.9(5) . . ?
C2 C1 O1 116.9(5) . . ?
C2 C1 C14 121.2(5) . . ?
C1 C2 C3 121.6(4) . . ?
C1 C2 C15 119.1(4) . . ?
C15 C2 C3 119.3(5) . . ?
C4 C3 C2 120.1(5) . . ?
C3 C4 C5 122.2(5) . . ?
C6 C5 C4 123.0(6) . . ?
C6 C5 C16 118.8(5) . . ?
C16 C5 C4 118.2(5) . . ?
C7 C6 C5 120.5(7) . . ?
C8 C7 C6 120.9(7) . . ?
C7 C8 C9 121.4(6) . . ?
C8 C9 C10 123.6(6) . . ?
C8 C9 C16 119.0(6) . . ?
C10 C9 C16 117.4(5) . . ?
C11 C10 C9 122.3(5) . . ?
C10 C11 C12 122.0(6) . . ?
C11 C12 C15 118.2(5) . . ?
C13 C12 C11 123.6(5) . . ?
C13 C12 C15 118.2(4) . . ?
C14 C13 C12 121.5(5) . . ?
C13 C14 C1 119.9(5) . . ?
C2 C15 C12 120.2(5) . . ?
C2 C15 C16 119.9(5) . . ?
C16 C15 C12 119.9(4) . . ?
C5 C16 C9 119.4(5) . . ?
C15 C16 C5 120.3(4) . . ?
C15 C16 C9 120.2(5) . . ?
O2 C21 C22 117.0(5) . . ?
O2 C21 C34 121.0(5) . . ?
C34 C21 C22 121.9(5) . . ?
C21 C22 C23 122.7(5) . . ?
C21 C22 C35 118.5(5) . . ?
C35 C22 C23 118.8(5) . . ?
C24 C23 C22 120.6(5) . . ?
C23 C24 C25 121.7(5) . . ?
C24 C25 C26 122.6(6) . . ?
C24 C25 C36 118.8(5) . . ?
C36 C25 C26 118.7(5) . . ?
C27 C26 C25 120.6(6) . . ?
C26 C27 C28 121.2(6) . . ?
C29 C28 C27 120.6(6) . . ?
C28 C29 C30 122.8(6) . . ?
C28 C29 C36 119.3(6) . . ?
C36 C29 C30 117.9(6) . . ?
C31 C30 C29 121.6(5) . . ?
C30 C31 C32 122.3(6) . . ?
C33 C32 C31 123.0(5) . . ?
C33 C32 C35 119.4(5) . . ?
C35 C32 C31 117.6(5) . . ?
C32 C33 C34 120.9(5) . . ?
C21 C34 C33 119.5(5) . . ?
C22 C35 C32 119.7(5) . . ?
C36 C35 C22 119.7(4) . . ?
C36 C35 C32 120.6(5) . . ?
C25 C36 C29 119.7(5) . . ?
C35 C36 C25 120.4(5) . . ?
C35 C36 C29 119.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.455(4)
2 0.545(4)

####################################################################### 
# 
# 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_t160
_database_code_depnum_ccdc_archive 'CCDC 1892296'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7827(5)
_cell_length_b                   4.54004(14)
_cell_length_c                   16.5843(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.974(3)
_cell_angle_gamma                90
_cell_volume                     1037.75(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4113
_cell_measurement_temperature    159.98(10)
_cell_measurement_theta_max      74.0400
_cell_measurement_theta_min      2.6660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6131
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         2.664
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1014692000
_diffrn_orient_matrix_UB_12      -0.1411046000
_diffrn_orient_matrix_UB_13      0.0041546000
_diffrn_orient_matrix_UB_21      0.0006837000
_diffrn_orient_matrix_UB_22      -0.0324371000
_diffrn_orient_matrix_UB_23      -0.0925117000
_diffrn_orient_matrix_UB_31      0.0467908000
_diffrn_orient_matrix_UB_32      0.3068403000
_diffrn_orient_matrix_UB_33      -0.0078120000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_full    0.659
_reflns_Friedel_fraction_max     0.672
_reflns_number_gt                2908
_reflns_number_total             2997
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.545(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.044
_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)+(0.0954P)²+0.0488P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1280
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.455(3)
 0.545(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6412(2) 0.7276(8) 0.42715(17) 0.0302(7) Uani 1 1 d D . . . .
C1 C 0.7177(3) 0.6858(11) 0.4805(2) 0.0221(9) Uani 1 1 d . . . . .
C2 C 0.7012(3) 0.4885(11) 0.5434(3) 0.0214(9) Uani 1 1 d . . . . .
C3 C 0.6082(3) 0.3486(11) 0.5551(2) 0.0245(10) Uani 1 1 d . . . . .
H3 H 0.5571 0.3898 0.5202 0.029 Uiso 1 1 calc R . . . .
C4 C 0.5955(3) 0.1559(11) 0.6173(3) 0.0286(10) Uani 1 1 d . . . . .
H4 H 0.5351 0.0677 0.6241 0.034 Uiso 1 1 calc R . . . .
C5 C 0.6715(3) 0.0852(11) 0.6721(3) 0.0256(9) Uani 1 1 d . . . . .
C6 C 0.6599(4) -0.1113(13) 0.7367(3) 0.0373(11) Uani 1 1 d . . . . .
H6 H 0.6004 -0.2035 0.7446 0.045 Uiso 1 1 calc R . . . .
C7 C 0.7359(5) -0.1697(15) 0.7889(3) 0.0436(14) Uani 1 1 d . . . . .
H7 H 0.7270 -0.3027 0.8309 0.052 Uiso 1 1 calc R . . . .
C8 C 0.8246(5) -0.0331(14) 0.7794(3) 0.0432(14) Uani 1 1 d . . . . .
H8 H 0.8740 -0.0709 0.8161 0.052 Uiso 1 1 calc R . . . .
C9 C 0.8413(3) 0.1584(11) 0.7164(3) 0.0307(11) Uani 1 1 d . . . . .
C10 C 0.9323(3) 0.3018(12) 0.7031(3) 0.0342(12) Uani 1 1 d . . . . .
H10 H 0.9834 0.2637 0.7382 0.041 Uiso 1 1 calc R . . . .
C11 C 0.9465(3) 0.4903(13) 0.6414(3) 0.0314(11) Uani 1 1 d . . . . .
H11 H 1.0071 0.5774 0.6348 0.038 Uiso 1 1 calc R . . . .
C12 C 0.8701(3) 0.5594(11) 0.5858(2) 0.0249(9) Uani 1 1 d . . . . .
C13 C 0.8827(3) 0.7587(11) 0.5224(3) 0.0270(10) Uani 1 1 d . . . . .
H13 H 0.9424 0.8508 0.5154 0.032 Uiso 1 1 calc R . . . .
C14 C 0.8073(3) 0.8207(11) 0.4699(3) 0.0272(10) Uani 1 1 d . . . . .
H14 H 0.8166 0.9523 0.4277 0.033 Uiso 1 1 calc R . . . .
C15 C 0.7781(3) 0.4226(11) 0.5967(2) 0.0206(9) Uani 1 1 d . . . . .
C16 C 0.7631(3) 0.2247(12) 0.6615(3) 0.0239(9) Uani 1 1 d . . . . .
O2 O 0.3697(2) 0.7297(9) 0.66483(18) 0.0316(7) Uani 1 1 d D . . . .
C21 C 0.3007(3) 0.6762(11) 0.7225(2) 0.0235(9) Uani 1 1 d . . . . .
C22 C 0.3236(3) 0.4736(10) 0.7831(3) 0.0222(9) Uani 1 1 d . . . . .
C23 C 0.4193(3) 0.3457(11) 0.7909(3) 0.0251(10) Uani 1 1 d . . . . .
H23 H 0.4676 0.3955 0.7541 0.030 Uiso 1 1 calc R . . . .
C24 C 0.4389(3) 0.1546(11) 0.8511(3) 0.0300(11) Uani 1 1 d . . . . .
H24 H 0.5011 0.0763 0.8550 0.036 Uiso 1 1 calc R . . . .
C25 C 0.3681(3) 0.0694(11) 0.9084(3) 0.0258(9) Uani 1 1 d . . . . .
C26 C 0.3867(4) -0.1318(13) 0.9716(3) 0.0319(11) Uani 1 1 d . . . . .
H26 H 0.4482 -0.2147 0.9765 0.038 Uiso 1 1 calc R . . . .
C27 C 0.3158(4) -0.2068(12) 1.0259(3) 0.0365(12) Uani 1 1 d . . . . .
H27 H 0.3301 -0.3372 1.0674 0.044 Uiso 1 1 calc R . . . .
C28 C 0.2223(4) -0.0904(12) 1.0196(3) 0.0347(12) Uani 1 1 d . . . . .
H28 H 0.1745 -0.1470 1.0560 0.042 Uiso 1 1 calc R . . . .
C29 C 0.2008(3) 0.1090(12) 0.9592(3) 0.0283(10) Uani 1 1 d . . . . .
C30 C 0.1049(3) 0.2379(14) 0.9502(3) 0.0337(11) Uani 1 1 d . . . . .
H30 H 0.0560 0.1846 0.9861 0.040 Uiso 1 1 calc R . . . .
C31 C 0.0853(3) 0.4316(13) 0.8916(3) 0.0334(12) Uani 1 1 d . . . . .
H31 H 0.0231 0.5100 0.8881 0.040 Uiso 1 1 calc R . . . .
C32 C 0.1569(3) 0.5218(11) 0.8343(3) 0.0257(9) Uani 1 1 d . . . . .
C33 C 0.1379(3) 0.7288(11) 0.7739(3) 0.0279(9) Uani 1 1 d . . . . .
H33 H 0.0772 0.8170 0.7710 0.034 Uiso 1 1 calc R . . . .
C34 C 0.2091(3) 0.8042(11) 0.7180(3) 0.0270(10) Uani 1 1 d . . . . .
H34 H 0.1955 0.9401 0.6776 0.032 Uiso 1 1 calc R . . . .
C35 C 0.2517(3) 0.3982(10) 0.8401(2) 0.0198(9) Uani 1 1 d . . . . .
C36 C 0.2730(3) 0.1932(12) 0.9024(2) 0.0229(9) Uani 1 1 d . . . . .
H1 H 0.647(3) 0.895(6) 0.408(2) 0.018(12) Uiso 1 1 d D . . . .
H2 H 0.366(7) 0.873(13) 0.634(4) 0.11(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.391(5) . ?
C1 C2 1.393(7) . ?
C1 C14 1.389(6) . ?
C2 C3 1.443(6) . ?
C2 C15 1.412(5) . ?
C3 C4 1.364(7) . ?
C4 C5 1.425(7) . ?
C5 C6 1.403(7) . ?
C5 C16 1.423(6) . ?
C6 C7 1.384(8) . ?
C7 C8 1.380(10) . ?
C8 C9 1.378(8) . ?
C9 C10 1.429(7) . ?
C9 C16 1.443(6) . ?
C10 C11 1.347(7) . ?
C11 C12 1.435(6) . ?
C12 C13 1.398(7) . ?
C12 C15 1.423(6) . ?
C13 C14 1.385(6) . ?
C15 C16 1.416(7) . ?
O2 C21 1.370(5) . ?
C21 C22 1.398(7) . ?
C21 C34 1.391(6) . ?
C22 C23 1.447(6) . ?
C22 C35 1.411(6) . ?
C23 C24 1.351(7) . ?
C24 C25 1.417(6) . ?
C25 C26 1.414(7) . ?
C25 C36 1.429(7) . ?
C26 C27 1.371(7) . ?
C27 C28 1.397(8) . ?
C28 C29 1.382(8) . ?
C29 C30 1.453(7) . ?
C29 C36 1.422(6) . ?
C30 C31 1.338(8) . ?
C31 C32 1.431(6) . ?
C32 C33 1.398(7) . ?
C32 C35 1.425(6) . ?
C33 C34 1.392(6) . ?
C35 C36 1.423(7) . ?

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 C1 C2 116.1(4) . . ?
C14 C1 O1 122.3(4) . . ?
C14 C1 C2 121.5(4) . . ?
C1 C2 C3 121.9(4) . . ?
C1 C2 C15 118.8(4) . . ?
C15 C2 C3 119.3(4) . . ?
C4 C3 C2 119.8(4) . . ?
C3 C4 C5 122.2(4) . . ?
C6 C5 C4 123.1(4) . . ?
C6 C5 C16 118.6(4) . . ?
C16 C5 C4 118.3(4) . . ?
C7 C6 C5 120.9(5) . . ?
C8 C7 C6 120.9(5) . . ?
C9 C8 C7 121.2(5) . . ?
C8 C9 C10 123.4(5) . . ?
C8 C9 C16 119.0(5) . . ?
C10 C9 C16 117.6(4) . . ?
C11 C10 C9 122.3(4) . . ?
C10 C11 C12 121.3(4) . . ?
C13 C12 C11 122.3(4) . . ?
C13 C12 C15 119.2(4) . . ?
C15 C12 C11 118.5(4) . . ?
C14 C13 C12 120.8(4) . . ?
C13 C14 C1 119.9(4) . . ?
C2 C15 C12 119.8(4) . . ?
C2 C15 C16 120.0(4) . . ?
C16 C15 C12 120.2(4) . . ?
C5 C16 C9 119.5(4) . . ?
C15 C16 C5 120.4(4) . . ?
C15 C16 C9 120.1(4) . . ?
O2 C21 C22 117.5(4) . . ?
O2 C21 C34 121.2(4) . . ?
C34 C21 C22 121.2(4) . . ?
C21 C22 C23 122.3(4) . . ?
C21 C22 C35 118.8(4) . . ?
C35 C22 C23 118.9(4) . . ?
C24 C23 C22 120.4(4) . . ?
C23 C24 C25 122.2(4) . . ?
C24 C25 C36 118.5(4) . . ?
C26 C25 C24 123.3(4) . . ?
C26 C25 C36 118.2(4) . . ?
C27 C26 C25 121.1(5) . . ?
C26 C27 C28 121.0(5) . . ?
C29 C28 C27 120.0(5) . . ?
C28 C29 C30 122.2(4) . . ?
C28 C29 C36 120.3(5) . . ?
C36 C29 C30 117.4(5) . . ?
C31 C30 C29 121.5(4) . . ?
C30 C31 C32 122.1(4) . . ?
C33 C32 C31 122.7(4) . . ?
C33 C32 C35 119.0(4) . . ?
C35 C32 C31 118.3(4) . . ?
C34 C33 C32 120.7(4) . . ?
C21 C34 C33 120.0(4) . . ?
C22 C35 C32 120.2(4) . . ?
C22 C35 C36 120.0(4) . . ?
C36 C35 C32 119.8(4) . . ?
C29 C36 C25 119.3(4) . . ?
C29 C36 C35 120.8(4) . . ?
C35 C36 C25 119.8(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.455(3)
2 0.545(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_t260
_database_code_depnum_ccdc_archive 'CCDC 1892307'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8462(7)
_cell_length_b                   4.56671(18)
_cell_length_c                   16.6389(7)
_cell_angle_alpha                90
_cell_angle_beta                 89.992(4)
_cell_angle_gamma                90
_cell_volume                     1052.11(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3400
_cell_measurement_temperature    259.98(10)
_cell_measurement_theta_max      74.6610
_cell_measurement_theta_min      2.6530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6276
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         2.656
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      259.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1009989000
_diffrn_orient_matrix_UB_12      -0.1408068000
_diffrn_orient_matrix_UB_13      0.0033827000
_diffrn_orient_matrix_UB_21      0.0000462000
_diffrn_orient_matrix_UB_22      -0.0297524000
_diffrn_orient_matrix_UB_23      -0.0922542000
_diffrn_orient_matrix_UB_31      0.0467197000
_diffrn_orient_matrix_UB_32      0.3049448000
_diffrn_orient_matrix_UB_33      -0.0074035000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.522
_reflns_Friedel_fraction_full    0.678
_reflns_Friedel_fraction_max     0.686
_reflns_number_gt                2844
_reflns_number_total             3062
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.543(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.055
_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)+(0.0893P)²+0.0383P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1319
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.457(3)
 0.543(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
3.b Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6427(2) 0.7236(9) 0.42727(18) 0.0475(8) Uani 1 1 d . . . . .
H1 H 0.6451 0.8906 0.4092 0.071 Uiso 1 1 calc R . . . .
C1 C 0.7182(3) 0.6819(12) 0.4809(3) 0.0373(10) Uani 1 1 d . . . . .
C2 C 0.7019(3) 0.4850(11) 0.5435(3) 0.0341(9) Uani 1 1 d . . . . .
C3 C 0.6088(3) 0.3462(12) 0.5546(3) 0.0396(11) Uani 1 1 d . . . . .
H3 H 0.5581 0.3870 0.5196 0.048 Uiso 1 1 calc R . . . .
C4 C 0.5960(4) 0.1559(12) 0.6164(3) 0.0444(12) Uani 1 1 d . . . . .
H4 H 0.5359 0.0681 0.6229 0.053 Uiso 1 1 calc R . . . .
C5 C 0.6710(4) 0.0856(11) 0.6717(3) 0.0417(10) Uani 1 1 d . . . . .
C6 C 0.6590(5) -0.1105(15) 0.7362(3) 0.0586(14) Uani 1 1 d . . . . .
H6 H 0.5999 -0.2029 0.7439 0.070 Uiso 1 1 calc R . . . .
C7 C 0.7348(6) -0.1669(17) 0.7885(3) 0.0686(19) Uani 1 1 d . . . . .
H7 H 0.7259 -0.2995 0.8303 0.082 Uiso 1 1 calc R . . . .
C8 C 0.8227(6) -0.0313(16) 0.7799(4) 0.069(2) Uani 1 1 d . . . . .
H8 H 0.8714 -0.0675 0.8171 0.083 Uiso 1 1 calc R . . . .
C9 C 0.8396(4) 0.1584(13) 0.7167(3) 0.0500(13) Uani 1 1 d . . . . .
C10 C 0.9301(4) 0.3004(14) 0.7037(3) 0.0549(15) Uani 1 1 d . . . . .
H10 H 0.9806 0.2629 0.7391 0.066 Uiso 1 1 calc R . . . .
C11 C 0.9450(4) 0.4863(15) 0.6425(3) 0.0529(14) Uani 1 1 d . . . . .
H11 H 1.0055 0.5715 0.6362 0.063 Uiso 1 1 calc R . . . .
C12 C 0.8699(3) 0.5562(12) 0.5865(3) 0.0401(11) Uani 1 1 d . . . . .
C13 C 0.8822(3) 0.7522(13) 0.5233(3) 0.0464(12) Uani 1 1 d . . . . .
H13 H 0.9417 0.8428 0.5162 0.056 Uiso 1 1 calc R . . . .
C14 C 0.8075(4) 0.8146(13) 0.4708(3) 0.0460(12) Uani 1 1 d . . . . .
H14 H 0.8171 0.9456 0.4288 0.055 Uiso 1 1 calc R . . . .
C15 C 0.7782(3) 0.4209(12) 0.5971(2) 0.0333(10) Uani 1 1 d . . . . .
C16 C 0.7623(3) 0.2234(13) 0.6621(3) 0.0375(10) Uani 1 1 d . . . . .
C21 C 0.3003(3) 0.6744(12) 0.7225(3) 0.0380(10) Uani 1 1 d . . . . .
O2 O 0.3690(2) 0.7258(9) 0.66466(18) 0.0492(8) Uani 1 1 d . . . . .
H2 H 0.3600 0.8877 0.6447 0.074 Uiso 1 1 calc R . . . .
C22 C 0.3238(3) 0.4742(11) 0.7827(3) 0.0346(10) Uani 1 1 d . . . . .
C23 C 0.4183(3) 0.3456(12) 0.7904(3) 0.0408(11) Uani 1 1 d . . . . .
H23 H 0.4663 0.3937 0.7535 0.049 Uiso 1 1 calc R . . . .
C24 C 0.4380(3) 0.1559(12) 0.8505(3) 0.0470(12) Uani 1 1 d . . . . .
H24 H 0.4998 0.0769 0.8543 0.056 Uiso 1 1 calc R . . . .
C25 C 0.3675(4) 0.0734(12) 0.9079(3) 0.0433(11) Uani 1 1 d . . . . .
C26 C 0.3871(4) -0.1272(15) 0.9708(3) 0.0551(14) Uani 1 1 d . . . . .
H26 H 0.4481 -0.2106 0.9755 0.066 Uiso 1 1 calc R . . . .
C27 C 0.3157(5) -0.1985(14) 1.0250(4) 0.0589(16) Uani 1 1 d . . . . .
H27 H 0.3296 -0.3287 1.0664 0.071 Uiso 1 1 calc R . . . .
C28 C 0.2237(5) -0.0814(15) 1.0195(3) 0.0563(15) Uani 1 1 d . . . . .
H28 H 0.1768 -0.1355 1.0566 0.068 Uiso 1 1 calc R . . . .
C29 C 0.2011(4) 0.1162(13) 0.9590(3) 0.0465(13) Uani 1 1 d . . . . .
C30 C 0.1070(4) 0.2449(17) 0.9502(4) 0.0560(15) Uani 1 1 d . . . . .
H30 H 0.0585 0.1927 0.9861 0.067 Uiso 1 1 calc R . . . .
C31 C 0.0872(4) 0.4366(16) 0.8922(3) 0.0542(15) Uani 1 1 d . . . . .
H31 H 0.0254 0.5159 0.8892 0.065 Uiso 1 1 calc R . . . .
C32 C 0.1581(3) 0.5244(12) 0.8344(3) 0.0418(11) Uani 1 1 d . . . . .
C33 C 0.1393(3) 0.7273(14) 0.7742(3) 0.0469(11) Uani 1 1 d . . . . .
H33 H 0.0787 0.8150 0.7715 0.056 Uiso 1 1 calc R . . . .
C34 C 0.2095(4) 0.8018(12) 0.7178(3) 0.0436(11) Uani 1 1 d . . . . .
H34 H 0.1957 0.9359 0.6773 0.052 Uiso 1 1 calc R . . . .
C35 C 0.2521(3) 0.3996(11) 0.8401(3) 0.0345(10) Uani 1 1 d . . . . .
C36 C 0.2737(3) 0.1971(13) 0.9022(3) 0.0372(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.388(5) . ?
C1 C2 1.395(7) . ?
C1 C14 1.386(7) . ?
C2 C3 1.449(6) . ?
C2 C15 1.412(6) . ?
C3 C4 1.359(7) . ?
C4 C5 1.424(7) . ?
C5 C6 1.408(7) . ?
C5 C16 1.422(7) . ?
C6 C7 1.387(9) . ?
C7 C8 1.372(11) . ?
C8 C9 1.383(9) . ?
C9 C10 1.427(8) . ?
C9 C16 1.434(6) . ?
C10 C11 1.343(8) . ?
C11 C12 1.432(7) . ?
C12 C13 1.391(8) . ?
C12 C15 1.423(6) . ?
C13 C14 1.384(7) . ?
C15 C16 1.426(7) . ?
C21 O2 1.373(5) . ?
C21 C22 1.395(7) . ?
C21 C34 1.387(7) . ?
C22 C23 1.440(7) . ?
C22 C35 1.419(6) . ?
C23 C24 1.351(8) . ?
C24 C25 1.417(7) . ?
C25 C26 1.417(8) . ?
C25 C36 1.419(7) . ?
C26 C27 1.377(8) . ?
C27 C28 1.384(9) . ?
C28 C29 1.388(9) . ?
C29 C30 1.437(9) . ?
C29 C36 1.428(6) . ?
C30 C31 1.331(9) . ?
C31 C32 1.432(7) . ?
C32 C33 1.389(8) . ?
C32 C35 1.424(7) . ?
C33 C34 1.394(7) . ?
C35 C36 1.418(7) . ?

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 C1 C2 116.6(4) . . ?
C14 C1 O1 122.2(5) . . ?
C14 C1 C2 121.1(4) . . ?
C1 C2 C3 121.4(4) . . ?
C1 C2 C15 118.9(4) . . ?
C15 C2 C3 119.7(4) . . ?
C4 C3 C2 119.5(4) . . ?
C3 C4 C5 122.6(5) . . ?
C6 C5 C4 123.4(5) . . ?
C6 C5 C16 118.1(5) . . ?
C16 C5 C4 118.5(4) . . ?
C7 C6 C5 120.5(6) . . ?
C8 C7 C6 121.4(6) . . ?
C7 C8 C9 120.8(6) . . ?
C8 C9 C10 123.3(5) . . ?
C8 C9 C16 118.9(6) . . ?
C10 C9 C16 117.8(5) . . ?
C11 C10 C9 122.4(5) . . ?
C10 C11 C12 121.5(5) . . ?
C13 C12 C11 123.1(5) . . ?
C13 C12 C15 118.8(4) . . ?
C15 C12 C11 118.1(5) . . ?
C14 C13 C12 121.2(4) . . ?
C13 C14 C1 120.0(5) . . ?
C2 C15 C12 119.9(4) . . ?
C2 C15 C16 119.7(4) . . ?
C12 C15 C16 120.4(4) . . ?
C5 C16 C9 120.1(5) . . ?
C5 C16 C15 120.1(4) . . ?
C15 C16 C9 119.7(4) . . ?
O2 C21 C22 117.0(4) . . ?
O2 C21 C34 121.1(4) . . ?
C34 C21 C22 121.8(4) . . ?
C21 C22 C23 122.9(4) . . ?
C21 C22 C35 118.5(4) . . ?
C35 C22 C23 118.6(4) . . ?
C24 C23 C22 120.7(4) . . ?
C23 C24 C25 122.1(5) . . ?
C24 C25 C36 118.6(5) . . ?
C26 C25 C24 122.6(5) . . ?
C26 C25 C36 118.8(5) . . ?
C27 C26 C25 119.9(6) . . ?
C26 C27 C28 121.7(6) . . ?
C27 C28 C29 120.5(6) . . ?
C28 C29 C30 123.0(5) . . ?
C28 C29 C36 119.3(6) . . ?
C36 C29 C30 117.7(5) . . ?
C31 C30 C29 122.0(5) . . ?
C30 C31 C32 122.0(5) . . ?
C33 C32 C31 122.9(5) . . ?
C33 C32 C35 119.1(5) . . ?
C35 C32 C31 118.0(5) . . ?
C32 C33 C34 121.2(5) . . ?
C21 C34 C33 119.4(5) . . ?
C22 C35 C32 119.9(5) . . ?
C36 C35 C22 119.9(4) . . ?
C36 C35 C32 120.2(4) . . ?
C25 C36 C29 119.8(5) . . ?
C35 C36 C25 120.1(4) . . ?
C35 C36 C29 120.1(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.457(3)
2 0.543(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_t310
_database_code_depnum_ccdc_archive 'CCDC 1892309'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8767(10)
_cell_length_b                   4.5831(3)
_cell_length_c                   16.6695(11)
_cell_angle_alpha                90
_cell_angle_beta                 89.995(6)
_cell_angle_gamma                90
_cell_volume                     1060.16(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2692
_cell_measurement_temperature    310.02(10)
_cell_measurement_theta_max      75.0610
_cell_measurement_theta_min      2.6450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6259
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         2.651
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      310.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1008768000
_diffrn_orient_matrix_UB_12      -0.1392669000
_diffrn_orient_matrix_UB_13      0.0042875000
_diffrn_orient_matrix_UB_21      0.0012559000
_diffrn_orient_matrix_UB_22      -0.0298261000
_diffrn_orient_matrix_UB_23      -0.0920752000
_diffrn_orient_matrix_UB_31      0.0463825000
_diffrn_orient_matrix_UB_32      0.3043278000
_diffrn_orient_matrix_UB_33      -0.0069842000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.524
_reflns_Friedel_fraction_full    0.680
_reflns_Friedel_fraction_max     0.687
_reflns_number_gt                2668
_reflns_number_total             3081
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.552(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3081
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.036
_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)+(0.1250P)²+0.0694P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1729
_refine_ls_wR_factor_ref         0.1867
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.448(5)
 0.552(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6433(4) 0.7223(13) 0.4277(3) 0.0600(12) Uani 1 1 d D . . . .
C1 C 0.7186(5) 0.6800(16) 0.4814(4) 0.0471(15) Uani 1 1 d . . . . .
C2 C 0.7024(4) 0.4836(16) 0.5437(4) 0.0434(13) Uani 1 1 d . . . . .
C3 C 0.6093(4) 0.3458(18) 0.5544(4) 0.0515(17) Uani 1 1 d . . . . .
H3 H 0.5589 0.3879 0.5196 0.062 Uiso 1 1 calc R . . . .
C4 C 0.5961(5) 0.1542(18) 0.6160(4) 0.0544(17) Uani 1 1 d . . . . .
H4 H 0.5363 0.0655 0.6221 0.065 Uiso 1 1 calc R . . . .
C5 C 0.6710(6) 0.0853(17) 0.6714(4) 0.0525(15) Uani 1 1 d . . . . .
C6 C 0.6581(7) -0.111(2) 0.7349(5) 0.072(2) Uani 1 1 d . . . . .
H6 H 0.5993 -0.2051 0.7414 0.086 Uiso 1 1 calc R . . . .
C7 C 0.7330(9) -0.165(2) 0.7882(5) 0.084(3) Uani 1 1 d . . . . .
H7 H 0.7231 -0.2926 0.8308 0.100 Uiso 1 1 calc R . . . .
C8 C 0.8214(9) -0.033(2) 0.7792(6) 0.085(3) Uani 1 1 d . . . . .
H8 H 0.8704 -0.0749 0.8156 0.102 Uiso 1 1 calc R . . . .
C9 C 0.8387(6) 0.1599(18) 0.7170(4) 0.061(2) Uani 1 1 d . . . . .
C10 C 0.9291(6) 0.300(2) 0.7038(5) 0.069(2) Uani 1 1 d . . . . .
H10 H 0.9796 0.2591 0.7388 0.083 Uiso 1 1 calc R . . . .
C11 C 0.9446(5) 0.488(2) 0.6430(5) 0.067(2) Uani 1 1 d . . . . .
H11 H 1.0047 0.5748 0.6374 0.081 Uiso 1 1 calc R . . . .
C12 C 0.8701(4) 0.5545(17) 0.5872(4) 0.0501(15) Uani 1 1 d . . . . .
C13 C 0.8816(5) 0.749(2) 0.5241(5) 0.0600(19) Uani 1 1 d . . . . .
H13 H 0.9407 0.8419 0.5173 0.072 Uiso 1 1 calc R . . . .
C14 C 0.8073(5) 0.8095(19) 0.4712(5) 0.0582(18) Uani 1 1 d . . . . .
H14 H 0.8174 0.9375 0.4287 0.070 Uiso 1 1 calc R . . . .
C15 C 0.7778(4) 0.4195(17) 0.5973(4) 0.0436(15) Uani 1 1 d . . . . .
C16 C 0.7621(5) 0.2234(17) 0.6618(4) 0.0472(15) Uani 1 1 d . . . . .
O2 O 0.3685(4) 0.7244(14) 0.6650(3) 0.0627(12) Uani 1 1 d D . . . .
C21 C 0.2998(5) 0.6728(16) 0.7230(4) 0.0476(15) Uani 1 1 d . . . . .
C22 C 0.3238(5) 0.4739(15) 0.7827(4) 0.0442(14) Uani 1 1 d . . . . .
C23 C 0.4181(5) 0.3468(17) 0.7906(4) 0.0523(16) Uani 1 1 d . . . . .
H23 H 0.4663 0.3960 0.7542 0.063 Uiso 1 1 calc R . . . .
C24 C 0.4373(5) 0.1566(18) 0.8503(4) 0.0584(19) Uani 1 1 d . . . . .
H24 H 0.4987 0.0760 0.8537 0.070 Uiso 1 1 calc R . . . .
C25 C 0.3674(5) 0.0758(17) 0.9079(4) 0.0538(16) Uani 1 1 d . . . . .
C26 C 0.3875(6) -0.124(2) 0.9705(4) 0.066(2) Uani 1 1 d . . . . .
H26 H 0.4484 -0.2066 0.9750 0.079 Uiso 1 1 calc R . . . .
C27 C 0.3163(7) -0.196(2) 1.0248(5) 0.073(2) Uani 1 1 d . . . . .
H27 H 0.3300 -0.3259 1.0660 0.087 Uiso 1 1 calc R . . . .
C28 C 0.2249(8) -0.078(2) 1.0189(5) 0.071(2) Uani 1 1 d . . . . .
H28 H 0.1782 -0.1316 1.0561 0.086 Uiso 1 1 calc R . . . .
C29 C 0.2010(6) 0.1205(19) 0.9588(4) 0.0587(19) Uani 1 1 d . . . . .
C30 C 0.1080(5) 0.247(2) 0.9500(5) 0.070(2) Uani 1 1 d . . . . .
H30 H 0.0595 0.1944 0.9857 0.084 Uiso 1 1 calc R . . . .
C31 C 0.0878(5) 0.439(2) 0.8923(5) 0.066(2) Uani 1 1 d . . . . .
H31 H 0.0262 0.5183 0.8894 0.079 Uiso 1 1 calc R . . . .
C32 C 0.1585(5) 0.5259(17) 0.8346(4) 0.0502(15) Uani 1 1 d . . . . .
C33 C 0.1397(5) 0.728(2) 0.7741(4) 0.0587(17) Uani 1 1 d . . . . .
H33 H 0.0793 0.8150 0.7713 0.070 Uiso 1 1 calc R . . . .
C34 C 0.2095(6) 0.8002(18) 0.7180(4) 0.0574(17) Uani 1 1 d . . . . .
H34 H 0.1958 0.9332 0.6775 0.069 Uiso 1 1 calc R . . . .
C35 C 0.2518(4) 0.4010(15) 0.8403(3) 0.0419(13) Uani 1 1 d . . . . .
C36 C 0.2743(5) 0.1998(17) 0.9024(4) 0.0467(14) Uani 1 1 d . . . . .
H1 H 0.651(8) 0.876(13) 0.403(5) 0.09(3) Uiso 1 1 d D . . . .
H2 H 0.357(9) 0.873(16) 0.638(6) 0.13(5) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.390(8) . ?
C1 C2 1.393(10) . ?
C1 C14 1.378(10) . ?
C2 C3 1.449(9) . ?
C2 C15 1.408(8) . ?
C3 C4 1.363(10) . ?
C4 C5 1.426(10) . ?
C5 C6 1.399(10) . ?
C5 C16 1.422(10) . ?
C6 C7 1.390(14) . ?
C7 C8 1.376(17) . ?
C8 C9 1.384(14) . ?
C9 C10 1.425(12) . ?
C9 C16 1.437(9) . ?
C10 C11 1.348(13) . ?
C11 C12 1.425(10) . ?
C12 C13 1.389(11) . ?
C12 C15 1.431(9) . ?
C13 C14 1.384(11) . ?
C15 C16 1.417(10) . ?
O2 C21 1.377(8) . ?
C21 C22 1.391(10) . ?
C21 C34 1.385(10) . ?
C22 C23 1.438(10) . ?
C22 C35 1.425(9) . ?
C23 C24 1.350(11) . ?
C24 C25 1.413(10) . ?
C25 C26 1.417(11) . ?
C25 C36 1.415(11) . ?
C26 C27 1.379(12) . ?
C27 C28 1.382(14) . ?
C28 C29 1.392(13) . ?
C29 C30 1.424(13) . ?
C29 C36 1.432(9) . ?
C30 C31 1.332(14) . ?
C31 C32 1.431(10) . ?
C32 C33 1.391(11) . ?
C32 C35 1.419(9) . ?
C33 C34 1.387(11) . ?
C35 C36 1.420(10) . ?

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 C1 C2 116.7(6) . . ?
C14 C1 O1 122.2(7) . . ?
C14 C1 C2 120.9(6) . . ?
C1 C2 C3 121.1(6) . . ?
C1 C2 C15 119.3(6) . . ?
C15 C2 C3 119.6(6) . . ?
C4 C3 C2 119.5(6) . . ?
C3 C4 C5 122.2(7) . . ?
C6 C5 C4 122.6(7) . . ?
C6 C5 C16 119.0(7) . . ?
C16 C5 C4 118.4(6) . . ?
C7 C6 C5 120.2(9) . . ?
C8 C7 C6 121.3(9) . . ?
C7 C8 C9 121.1(9) . . ?
C8 C9 C10 123.8(8) . . ?
C8 C9 C16 118.8(9) . . ?
C10 C9 C16 117.5(7) . . ?
C11 C10 C9 123.0(7) . . ?
C10 C11 C12 120.8(8) . . ?
C11 C12 C15 118.6(7) . . ?
C13 C12 C11 123.3(7) . . ?
C13 C12 C15 118.0(6) . . ?
C14 C13 C12 121.7(7) . . ?
C1 C14 C13 120.1(7) . . ?
C2 C15 C12 120.0(6) . . ?
C2 C15 C16 119.9(6) . . ?
C16 C15 C12 120.1(6) . . ?
C5 C16 C9 119.7(7) . . ?
C15 C16 C5 120.3(5) . . ?
C15 C16 C9 120.0(7) . . ?
O2 C21 C22 116.7(6) . . ?
O2 C21 C34 120.8(6) . . ?
C34 C21 C22 122.4(6) . . ?
C21 C22 C23 123.3(6) . . ?
C21 C22 C35 117.9(6) . . ?
C35 C22 C23 118.8(6) . . ?
C24 C23 C22 120.5(7) . . ?
C23 C24 C25 122.3(7) . . ?
C24 C25 C26 122.4(8) . . ?
C24 C25 C36 118.5(7) . . ?
C36 C25 C26 119.1(7) . . ?
C27 C26 C25 119.8(8) . . ?
C26 C27 C28 121.2(8) . . ?
C27 C28 C29 121.6(9) . . ?
C28 C29 C30 123.8(8) . . ?
C28 C29 C36 118.0(9) . . ?
C30 C29 C36 118.1(8) . . ?
C31 C30 C29 122.3(7) . . ?
C30 C31 C32 121.7(8) . . ?
C33 C32 C31 122.9(7) . . ?
C33 C32 C35 119.2(6) . . ?
C35 C32 C31 117.9(7) . . ?
C34 C33 C32 121.1(7) . . ?
C21 C34 C33 119.4(7) . . ?
C32 C35 C22 120.0(6) . . ?
C32 C35 C36 120.7(6) . . ?
C36 C35 C22 119.3(6) . . ?
C25 C36 C29 120.3(7) . . ?
C25 C36 C35 120.5(6) . . ?
C35 C36 C29 119.2(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.448(5)
2 0.552(5)

####################################################################### 
# 
# 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_t140
_database_code_depnum_ccdc_archive 'CCDC 1892310'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7702(4)
_cell_length_b                   4.53628(13)
_cell_length_c                   16.5687(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.989(3)
_cell_angle_gamma                90
_cell_volume                     1034.97(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4218
_cell_measurement_temperature    139.99(10)
_cell_measurement_theta_max      75.5070
_cell_measurement_theta_min      2.6660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6128
_diffrn_reflns_point_group_measured_fraction_full 0.843
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.914
_diffrn_reflns_theta_min         2.667
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1015614000
_diffrn_orient_matrix_UB_12      -0.1410927000
_diffrn_orient_matrix_UB_13      0.0042751000
_diffrn_orient_matrix_UB_21      0.0007235000
_diffrn_orient_matrix_UB_22      -0.0331341000
_diffrn_orient_matrix_UB_23      -0.0925775000
_diffrn_orient_matrix_UB_31      0.0467875000
_diffrn_orient_matrix_UB_32      0.3071655000
_diffrn_orient_matrix_UB_33      -0.0079501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.509
_reflns_Friedel_fraction_full    0.659
_reflns_Friedel_fraction_max     0.670
_reflns_number_gt                2939
_reflns_number_total             2993
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.546(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2993
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.044
_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)+(0.0922P)²+0.0859P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1235
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.454(3)
 0.546(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6407(2) 0.7285(8) 0.42709(17) 0.0297(6) Uani 1 1 d D . . . .
C1 C 0.7174(3) 0.6872(11) 0.4808(2) 0.0230(9) Uani 1 1 d . . . . .
C2 C 0.7009(3) 0.4889(10) 0.5432(2) 0.0218(9) Uani 1 1 d . . . . .
C3 C 0.6077(3) 0.3482(11) 0.5550(2) 0.0252(9) Uani 1 1 d . . . . .
H3 H 0.5565 0.3886 0.5202 0.030 Uiso 1 1 calc R . . . .
C4 C 0.5951(3) 0.1557(11) 0.6177(3) 0.0275(10) Uani 1 1 d . . . . .
H4 H 0.5347 0.0678 0.6248 0.033 Uiso 1 1 calc R . . . .
C5 C 0.6716(3) 0.0854(10) 0.6722(2) 0.0261(9) Uani 1 1 d . . . . .
C6 C 0.6598(4) -0.1128(12) 0.7367(3) 0.0359(10) Uani 1 1 d . . . . .
H6 H 0.6003 -0.2058 0.7442 0.043 Uiso 1 1 calc R . . . .
C7 C 0.7356(4) -0.1710(14) 0.7890(3) 0.0403(12) Uani 1 1 d . . . . .
H7 H 0.7265 -0.3040 0.8311 0.048 Uiso 1 1 calc R . . . .
C8 C 0.8251(4) -0.0348(12) 0.7799(3) 0.0390(12) Uani 1 1 d . . . . .
H8 H 0.8745 -0.0726 0.8167 0.047 Uiso 1 1 calc R . . . .
C9 C 0.8414(3) 0.1583(11) 0.7161(2) 0.0307(10) Uani 1 1 d . . . . .
C10 C 0.9326(3) 0.3021(12) 0.7029(3) 0.0330(11) Uani 1 1 d . . . . .
H10 H 0.9836 0.2644 0.7381 0.040 Uiso 1 1 calc R . . . .
C11 C 0.9469(3) 0.4910(12) 0.6410(3) 0.0315(10) Uani 1 1 d . . . . .
H11 H 1.0076 0.5774 0.6341 0.038 Uiso 1 1 calc R . . . .
C12 C 0.8702(3) 0.5603(10) 0.5858(2) 0.0253(9) Uani 1 1 d . . . . .
C13 C 0.8828(3) 0.7592(11) 0.5224(3) 0.0285(10) Uani 1 1 d . . . . .
H13 H 0.9426 0.8512 0.5153 0.034 Uiso 1 1 calc R . . . .
C14 C 0.8070(3) 0.8211(11) 0.4697(3) 0.0274(10) Uani 1 1 d . . . . .
H14 H 0.8162 0.9520 0.4272 0.033 Uiso 1 1 calc R . . . .
C15 C 0.7783(3) 0.4227(11) 0.5969(2) 0.0214(9) Uani 1 1 d . . . . .
C16 C 0.7630(3) 0.2245(12) 0.6617(2) 0.0257(9) Uani 1 1 d . . . . .
O2 O 0.3698(2) 0.7312(8) 0.66457(18) 0.0315(7) Uani 1 1 d D . . . .
C21 C 0.3003(3) 0.6776(10) 0.7226(2) 0.0236(9) Uani 1 1 d . . . . .
C22 C 0.3240(3) 0.4733(10) 0.7830(2) 0.0223(9) Uani 1 1 d . . . . .
C23 C 0.4196(3) 0.3455(11) 0.7910(3) 0.0255(9) Uani 1 1 d . . . . .
H23 H 0.4680 0.3953 0.7544 0.031 Uiso 1 1 calc R . . . .
C24 C 0.4392(3) 0.1539(10) 0.8514(3) 0.0294(10) Uani 1 1 d . . . . .
H24 H 0.5013 0.0751 0.8555 0.035 Uiso 1 1 calc R . . . .
C25 C 0.3682(3) 0.0697(11) 0.9086(2) 0.0267(9) Uani 1 1 d . . . . .
C26 C 0.3866(3) -0.1335(12) 0.9720(3) 0.0323(10) Uani 1 1 d . . . . .
H26 H 0.4480 -0.2170 0.9769 0.039 Uiso 1 1 calc R . . . .
C27 C 0.3156(4) -0.2087(12) 1.0261(3) 0.0355(11) Uani 1 1 d . . . . .
H27 H 0.3299 -0.3396 1.0676 0.043 Uiso 1 1 calc R . . . .
C28 C 0.2223(4) -0.0917(12) 1.0197(3) 0.0336(11) Uani 1 1 d . . . . .
H28 H 0.1745 -0.1481 1.0563 0.040 Uiso 1 1 calc R . . . .
C29 C 0.2004(3) 0.1087(11) 0.9591(2) 0.0281(10) Uani 1 1 d . . . . .
C30 C 0.1044(3) 0.2356(14) 0.9501(3) 0.0335(10) Uani 1 1 d . . . . .
H30 H 0.0554 0.1799 0.9855 0.040 Uiso 1 1 calc R . . . .
C31 C 0.0849(3) 0.4318(12) 0.8918(3) 0.0321(11) Uani 1 1 d . . . . .
H31 H 0.0228 0.5119 0.8885 0.038 Uiso 1 1 calc R . . . .
C32 C 0.1570(3) 0.5213(11) 0.8343(3) 0.0253(9) Uani 1 1 d . . . . .
C33 C 0.1379(3) 0.7288(11) 0.7739(2) 0.0273(9) Uani 1 1 d . . . . .
H33 H 0.0770 0.8172 0.7712 0.033 Uiso 1 1 calc R . . . .
C34 C 0.2090(3) 0.8048(11) 0.7177(3) 0.0276(9) Uani 1 1 d . . . . .
H34 H 0.1952 0.9401 0.6772 0.033 Uiso 1 1 calc R . . . .
C35 C 0.2518(3) 0.3987(10) 0.8403(2) 0.0200(8) Uani 1 1 d . . . . .
C36 C 0.2730(3) 0.1927(11) 0.9025(2) 0.0233(9) Uani 1 1 d . . . . .
H1 H 0.648(3) 0.898(6) 0.409(2) 0.021(12) Uiso 1 1 d D . . . .
H2 H 0.364(8) 0.891(13) 0.640(6) 0.15(5) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.394(5) . ?
C1 C2 1.390(6) . ?
C1 C14 1.386(6) . ?
C2 C3 1.446(6) . ?
C2 C15 1.421(5) . ?
C3 C4 1.367(6) . ?
C4 C5 1.424(6) . ?
C5 C6 1.405(7) . ?
C5 C16 1.419(6) . ?
C6 C7 1.384(7) . ?
C7 C8 1.386(9) . ?
C8 C9 1.391(7) . ?
C9 C10 1.432(7) . ?
C9 C16 1.438(6) . ?
C10 C11 1.351(7) . ?
C11 C12 1.431(6) . ?
C12 C13 1.395(7) . ?
C12 C15 1.423(6) . ?
C13 C14 1.390(6) . ?
C15 C16 1.417(6) . ?
O2 C21 1.378(5) . ?
C21 C22 1.402(7) . ?
C21 C34 1.385(6) . ?
C22 C23 1.444(6) . ?
C22 C35 1.416(6) . ?
C23 C24 1.353(7) . ?
C24 C25 1.414(6) . ?
C25 C26 1.421(7) . ?
C25 C36 1.428(6) . ?
C26 C27 1.369(7) . ?
C27 C28 1.395(8) . ?
C28 C29 1.388(7) . ?
C29 C30 1.449(7) . ?
C29 C36 1.423(6) . ?
C30 C31 1.341(8) . ?
C31 C32 1.434(6) . ?
C32 C33 1.399(6) . ?
C32 C35 1.422(5) . ?
C33 C34 1.394(6) . ?
C35 C36 1.421(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 115.9(4) . . ?
C14 C1 O1 122.1(4) . . ?
C14 C1 C2 121.9(4) . . ?
C1 C2 C3 122.2(4) . . ?
C1 C2 C15 118.6(4) . . ?
C15 C2 C3 119.2(4) . . ?
C4 C3 C2 119.8(4) . . ?
C3 C4 C5 122.1(4) . . ?
C6 C5 C4 122.7(4) . . ?
C6 C5 C16 118.7(4) . . ?
C16 C5 C4 118.6(4) . . ?
C7 C6 C5 120.7(5) . . ?
C6 C7 C8 121.2(5) . . ?
C7 C8 C9 120.4(5) . . ?
C8 C9 C10 123.0(4) . . ?
C8 C9 C16 119.1(4) . . ?
C10 C9 C16 117.9(4) . . ?
C11 C10 C9 122.2(4) . . ?
C10 C11 C12 121.1(4) . . ?
C13 C12 C11 122.1(4) . . ?
C13 C12 C15 119.4(4) . . ?
C15 C12 C11 118.5(4) . . ?
C14 C13 C12 120.7(4) . . ?
C1 C14 C13 119.8(4) . . ?
C2 C15 C12 119.6(4) . . ?
C16 C15 C2 119.8(4) . . ?
C16 C15 C12 120.6(4) . . ?
C5 C16 C9 119.7(4) . . ?
C15 C16 C5 120.5(3) . . ?
C15 C16 C9 119.8(4) . . ?
O2 C21 C22 116.9(4) . . ?
O2 C21 C34 121.0(4) . . ?
C34 C21 C22 121.9(4) . . ?
C21 C22 C23 122.9(4) . . ?
C21 C22 C35 118.2(4) . . ?
C35 C22 C23 118.8(4) . . ?
C24 C23 C22 120.5(4) . . ?
C23 C24 C25 122.1(4) . . ?
C24 C25 C26 123.2(4) . . ?
C24 C25 C36 118.8(4) . . ?
C26 C25 C36 118.0(4) . . ?
C27 C26 C25 121.2(5) . . ?
C26 C27 C28 120.9(5) . . ?
C29 C28 C27 120.3(5) . . ?
C28 C29 C30 122.2(4) . . ?
C28 C29 C36 120.0(5) . . ?
C36 C29 C30 117.8(4) . . ?
C31 C30 C29 121.4(4) . . ?
C30 C31 C32 121.8(4) . . ?
C33 C32 C31 122.4(4) . . ?
C33 C32 C35 119.0(4) . . ?
C35 C32 C31 118.6(4) . . ?
C34 C33 C32 120.8(4) . . ?
C21 C34 C33 119.7(4) . . ?
C22 C35 C32 120.3(4) . . ?
C22 C35 C36 119.9(3) . . ?
C36 C35 C32 119.7(4) . . ?
C29 C36 C25 119.6(4) . . ?
C35 C36 C25 119.8(4) . . ?
C35 C36 C29 120.6(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.454(3)
2 0.546(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_t210
_database_code_depnum_ccdc_archive 'CCDC 1892301'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8115(5)
_cell_length_b                   4.55378(14)
_cell_length_c                   16.6052(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.990(3)
_cell_angle_gamma                90
_cell_volume                     1044.37(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3726
_cell_measurement_temperature    210.02(10)
_cell_measurement_theta_max      75.0150
_cell_measurement_theta_min      4.1420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6195
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         2.661
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      210.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1012901000
_diffrn_orient_matrix_UB_12      -0.1404483000
_diffrn_orient_matrix_UB_13      -0.0043935000
_diffrn_orient_matrix_UB_21      -0.0010764000
_diffrn_orient_matrix_UB_22      -0.0319539000
_diffrn_orient_matrix_UB_23      0.0923960000
_diffrn_orient_matrix_UB_31      -0.0466335000
_diffrn_orient_matrix_UB_32      0.3060627000
_diffrn_orient_matrix_UB_33      0.0075772000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.515
_reflns_Friedel_fraction_full    0.665
_reflns_Friedel_fraction_max     0.676
_reflns_number_gt                2878
_reflns_number_total             3025
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.544(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.030
_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)+(0.0985P)²+0.0903P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1388
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.456(3)
 0.544(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6418(3) 0.7257(9) 0.4272(2) 0.0384(8) Uani 1 1 d D . . . .
C1 C 0.7177(3) 0.6838(12) 0.4809(3) 0.0296(10) Uani 1 1 d . . . . .
C2 C 0.7014(3) 0.4872(12) 0.5435(3) 0.0273(10) Uani 1 1 d . . . . .
C3 C 0.6083(3) 0.3464(12) 0.5549(3) 0.0313(11) Uani 1 1 d . . . . .
H3 H 0.5574 0.3864 0.5199 0.038 Uiso 1 1 calc R . . . .
C4 C 0.5955(4) 0.1557(13) 0.6170(3) 0.0351(12) Uani 1 1 d . . . . .
H4 H 0.5351 0.0684 0.6238 0.042 Uiso 1 1 calc R . . . .
C5 C 0.6714(4) 0.0847(12) 0.6720(3) 0.0335(11) Uani 1 1 d . . . . .
C6 C 0.6595(5) -0.1114(15) 0.7362(3) 0.0459(13) Uani 1 1 d . . . . .
H6 H 0.6001 -0.2041 0.7438 0.055 Uiso 1 1 calc R . . . .
C7 C 0.7352(6) -0.1686(17) 0.7886(3) 0.0555(17) Uani 1 1 d . . . . .
H7 H 0.7264 -0.3016 0.8304 0.067 Uiso 1 1 calc R . . . .
C8 C 0.8235(6) -0.0314(16) 0.7796(4) 0.0542(17) Uani 1 1 d . . . . .
H8 H 0.8725 -0.0674 0.8167 0.065 Uiso 1 1 calc R . . . .
C9 C 0.8405(4) 0.1593(13) 0.7162(3) 0.0398(13) Uani 1 1 d . . . . .
C10 C 0.9314(4) 0.3017(15) 0.7035(3) 0.0438(14) Uani 1 1 d . . . . .
H10 H 0.9821 0.2639 0.7388 0.053 Uiso 1 1 calc R . . . .
C11 C 0.9458(4) 0.4882(15) 0.6421(3) 0.0410(13) Uani 1 1 d . . . . .
H11 H 1.0064 0.5744 0.6357 0.049 Uiso 1 1 calc R . . . .
C12 C 0.8702(3) 0.5581(12) 0.5861(3) 0.0322(11) Uani 1 1 d . . . . .
C13 C 0.8822(3) 0.7562(14) 0.5231(3) 0.0374(12) Uani 1 1 d . . . . .
H13 H 0.9415 0.8496 0.5164 0.045 Uiso 1 1 calc R . . . .
C14 C 0.8074(4) 0.8165(13) 0.4705(3) 0.0370(12) Uani 1 1 d . . . . .
H14 H 0.8172 0.9461 0.4279 0.044 Uiso 1 1 calc R . . . .
C15 C 0.7783(3) 0.4225(12) 0.5967(3) 0.0266(10) Uani 1 1 d . . . . .
C16 C 0.7628(3) 0.2269(14) 0.6619(3) 0.0314(10) Uani 1 1 d . . . . .
O2 O 0.3692(3) 0.7279(10) 0.6649(2) 0.0407(8) Uani 1 1 d D . . . .
C21 C 0.3002(3) 0.6757(12) 0.7227(3) 0.0308(11) Uani 1 1 d . . . . .
C22 C 0.3241(4) 0.4731(12) 0.7833(3) 0.0295(10) Uani 1 1 d . . . . .
C23 C 0.4186(3) 0.3459(12) 0.7906(3) 0.0330(11) Uani 1 1 d . . . . .
H23 H 0.4666 0.3952 0.7537 0.040 Uiso 1 1 calc R . . . .
C24 C 0.4386(3) 0.1550(13) 0.8505(3) 0.0392(13) Uani 1 1 d . . . . .
H24 H 0.5004 0.0754 0.8541 0.047 Uiso 1 1 calc R . . . .
C25 C 0.3681(4) 0.0725(12) 0.9081(3) 0.0340(11) Uani 1 1 d . . . . .
C26 C 0.3871(4) -0.1299(15) 0.9714(3) 0.0428(13) Uani 1 1 d . . . . .
H26 H 0.4484 -0.2126 0.9764 0.051 Uiso 1 1 calc R . . . .
C27 C 0.3153(5) -0.2045(14) 1.0258(3) 0.0474(15) Uani 1 1 d . . . . .
H27 H 0.3290 -0.3360 1.0671 0.057 Uiso 1 1 calc R . . . .
C28 C 0.2233(5) -0.0861(15) 1.0195(3) 0.0456(14) Uani 1 1 d . . . . .
H28 H 0.1758 -0.1412 1.0562 0.055 Uiso 1 1 calc R . . . .
C29 C 0.2010(4) 0.1126(14) 0.9594(3) 0.0375(12) Uani 1 1 d . . . . .
C30 C 0.1060(4) 0.2407(17) 0.9504(3) 0.0443(14) Uani 1 1 d . . . . .
H30 H 0.0574 0.1875 0.9863 0.053 Uiso 1 1 calc R . . . .
C31 C 0.0857(4) 0.4333(15) 0.8921(3) 0.0433(14) Uani 1 1 d . . . . .
H31 H 0.0237 0.5117 0.8888 0.052 Uiso 1 1 calc R . . . .
C32 C 0.1575(3) 0.5222(12) 0.8344(3) 0.0327(10) Uani 1 1 d . . . . .
C33 C 0.1386(3) 0.7274(13) 0.7741(3) 0.0364(11) Uani 1 1 d . . . . .
H33 H 0.0780 0.8158 0.7714 0.044 Uiso 1 1 calc R . . . .
C34 C 0.2096(4) 0.8023(13) 0.7176(3) 0.0353(11) Uani 1 1 d . . . . .
H34 H 0.1959 0.9363 0.6769 0.042 Uiso 1 1 calc R . . . .
C35 C 0.2520(3) 0.3997(12) 0.8404(3) 0.0260(10) Uani 1 1 d . . . . .
C36 C 0.2734(3) 0.1958(13) 0.9023(3) 0.0307(11) Uani 1 1 d . . . . .
H1 H 0.649(4) 0.893(7) 0.409(3) 0.028(14) Uiso 1 1 d D . . . .
H2 H 0.360(5) 0.878(11) 0.637(4) 0.07(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.390(5) . ?
C1 C2 1.390(7) . ?
C1 C14 1.389(7) . ?
C2 C3 1.450(7) . ?
C2 C15 1.412(6) . ?
C3 C4 1.358(7) . ?
C4 C5 1.428(7) . ?
C5 C6 1.401(7) . ?
C5 C16 1.429(8) . ?
C6 C7 1.385(9) . ?
C7 C8 1.378(11) . ?
C8 C9 1.385(9) . ?
C9 C10 1.429(8) . ?
C9 C16 1.435(7) . ?
C10 C11 1.341(8) . ?
C11 C12 1.434(7) . ?
C12 C13 1.391(8) . ?
C12 C15 1.423(6) . ?
C13 C14 1.381(7) . ?
C15 C16 1.418(7) . ?
O2 C21 1.373(6) . ?
C21 C22 1.405(8) . ?
C21 C34 1.380(7) . ?
C22 C23 1.433(7) . ?
C22 C35 1.415(7) . ?
C23 C24 1.350(8) . ?
C24 C25 1.414(7) . ?
C25 C26 1.424(8) . ?
C25 C36 1.426(8) . ?
C26 C27 1.384(9) . ?
C27 C28 1.385(10) . ?
C28 C29 1.381(9) . ?
C29 C30 1.444(9) . ?
C29 C36 1.430(7) . ?
C30 C31 1.336(9) . ?
C31 C32 1.436(7) . ?
C32 C33 1.395(8) . ?
C32 C35 1.423(6) . ?
C33 C34 1.399(7) . ?
C35 C36 1.416(8) . ?

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 C1 C2 116.5(4) . . ?
C14 C1 O1 122.2(5) . . ?
C14 C1 C2 121.2(5) . . ?
C1 C2 C3 121.8(4) . . ?
C1 C2 C15 118.7(4) . . ?
C15 C2 C3 119.5(4) . . ?
C4 C3 C2 119.8(4) . . ?
C3 C4 C5 122.3(5) . . ?
C4 C5 C16 118.1(5) . . ?
C6 C5 C4 123.1(5) . . ?
C6 C5 C16 118.8(5) . . ?
C7 C6 C5 120.6(6) . . ?
C8 C7 C6 121.0(6) . . ?
C7 C8 C9 121.1(6) . . ?
C8 C9 C10 123.1(5) . . ?
C8 C9 C16 119.0(6) . . ?
C10 C9 C16 117.9(5) . . ?
C11 C10 C9 122.0(4) . . ?
C10 C11 C12 121.7(5) . . ?
C13 C12 C11 123.0(5) . . ?
C13 C12 C15 118.7(4) . . ?
C15 C12 C11 118.2(5) . . ?
C14 C13 C12 121.1(5) . . ?
C13 C14 C1 120.1(5) . . ?
C2 C15 C12 120.2(4) . . ?
C2 C15 C16 119.7(4) . . ?
C16 C15 C12 120.1(4) . . ?
C5 C16 C9 119.3(5) . . ?
C15 C16 C5 120.5(4) . . ?
C15 C16 C9 120.1(5) . . ?
O2 C21 C22 116.8(5) . . ?
O2 C21 C34 120.9(5) . . ?
C34 C21 C22 122.1(5) . . ?
C21 C22 C23 122.7(5) . . ?
C21 C22 C35 118.0(4) . . ?
C35 C22 C23 119.3(4) . . ?
C24 C23 C22 120.6(5) . . ?
C23 C24 C25 121.9(5) . . ?
C24 C25 C26 123.0(5) . . ?
C24 C25 C36 118.7(5) . . ?
C26 C25 C36 118.3(5) . . ?
C27 C26 C25 120.6(6) . . ?
C26 C27 C28 120.9(6) . . ?
C29 C28 C27 120.9(6) . . ?
C28 C29 C30 122.8(5) . . ?
C28 C29 C36 119.8(6) . . ?
C36 C29 C30 117.3(5) . . ?
C31 C30 C29 122.1(5) . . ?
C30 C31 C32 121.6(5) . . ?
C33 C32 C31 122.6(5) . . ?
C33 C32 C35 119.0(4) . . ?
C35 C32 C31 118.4(5) . . ?
C32 C33 C34 120.9(5) . . ?
C21 C34 C33 119.5(5) . . ?
C22 C35 C32 120.4(5) . . ?
C22 C35 C36 119.6(4) . . ?
C36 C35 C32 120.0(4) . . ?
C25 C36 C29 119.5(5) . . ?
C35 C36 C25 119.9(4) . . ?
C35 C36 C29 120.6(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.456(3)
2 0.544(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_t130
_database_code_depnum_ccdc_archive 'CCDC 1892311'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7678(4)
_cell_length_b                   4.53467(13)
_cell_length_c                   16.5652(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.975(3)
_cell_angle_gamma                90
_cell_volume                     1034.20(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4247
_cell_measurement_temperature    130.02(10)
_cell_measurement_theta_max      75.5490
_cell_measurement_theta_min      4.1450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6118
_diffrn_reflns_point_group_measured_fraction_full 0.844
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.956
_diffrn_reflns_theta_min         2.667
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1016056000
_diffrn_orient_matrix_UB_12      -0.1408148000
_diffrn_orient_matrix_UB_13      0.0045160000
_diffrn_orient_matrix_UB_21      0.0009807000
_diffrn_orient_matrix_UB_22      -0.0336286000
_diffrn_orient_matrix_UB_23      -0.0925866000
_diffrn_orient_matrix_UB_31      0.0467260000
_diffrn_orient_matrix_UB_32      0.3073618000
_diffrn_orient_matrix_UB_33      -0.0080052000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.508
_reflns_Friedel_fraction_full    0.658
_reflns_Friedel_fraction_max     0.669
_reflns_number_gt                2935
_reflns_number_total             2992
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.547(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.052
_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)+(0.0970P)²+0.0292P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1254
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.453(3)
 0.547(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6406(2) 0.7283(8) 0.42694(17) 0.0289(6) Uani 1 1 d D . . . .
C1 C 0.7171(3) 0.6878(10) 0.4810(2) 0.0224(9) Uani 1 1 d . . . . .
C2 C 0.7007(3) 0.4898(10) 0.5431(2) 0.0208(9) Uani 1 1 d . . . . .
C3 C 0.6078(3) 0.3484(11) 0.5552(2) 0.0236(9) Uani 1 1 d . . . . .
H3 H 0.5566 0.3885 0.5202 0.028 Uiso 1 1 calc R . . . .
C4 C 0.5949(3) 0.1560(10) 0.6176(3) 0.0258(9) Uani 1 1 d . . . . .
H4 H 0.5344 0.0689 0.6248 0.031 Uiso 1 1 calc R . . . .
C5 C 0.6713(3) 0.0846(10) 0.6721(2) 0.0251(9) Uani 1 1 d . . . . .
C6 C 0.6598(4) -0.1122(12) 0.7367(3) 0.0339(10) Uani 1 1 d . . . . .
H6 H 0.6003 -0.2044 0.7447 0.041 Uiso 1 1 calc R . . . .
C7 C 0.7360(4) -0.1714(14) 0.7888(3) 0.0389(12) Uani 1 1 d . . . . .
H7 H 0.7271 -0.3060 0.8306 0.047 Uiso 1 1 calc R . . . .
C8 C 0.8251(4) -0.0336(12) 0.7799(3) 0.0386(12) Uani 1 1 d . . . . .
H8 H 0.8743 -0.0696 0.8170 0.046 Uiso 1 1 calc R . . . .
C9 C 0.8413(3) 0.1577(11) 0.7161(2) 0.0294(10) Uani 1 1 d . . . . .
C10 C 0.9330(3) 0.3020(12) 0.7029(3) 0.0315(11) Uani 1 1 d . . . . .
H10 H 0.9842 0.2639 0.7381 0.038 Uiso 1 1 calc R . . . .
C11 C 0.9470(3) 0.4910(12) 0.6410(3) 0.0296(10) Uani 1 1 d . . . . .
H11 H 1.0077 0.5777 0.6342 0.035 Uiso 1 1 calc R . . . .
C12 C 0.8704(3) 0.5609(10) 0.5857(2) 0.0244(9) Uani 1 1 d . . . . .
C13 C 0.8827(3) 0.7603(11) 0.5223(3) 0.0263(9) Uani 1 1 d . . . . .
H13 H 0.9423 0.8537 0.5153 0.032 Uiso 1 1 calc R . . . .
C14 C 0.8068(3) 0.8208(11) 0.4696(3) 0.0263(10) Uani 1 1 d . . . . .
H14 H 0.8161 0.9502 0.4267 0.032 Uiso 1 1 calc R . . . .
C15 C 0.7783(3) 0.4233(11) 0.5965(2) 0.0200(9) Uani 1 1 d . . . . .
C16 C 0.7631(3) 0.2245(12) 0.6619(2) 0.0237(9) Uani 1 1 d . . . . .
O2 O 0.3701(2) 0.7317(8) 0.66485(17) 0.0299(7) Uani 1 1 d D . . . .
C21 C 0.3006(3) 0.6770(10) 0.7227(2) 0.0219(9) Uani 1 1 d . . . . .
C22 C 0.3239(3) 0.4735(10) 0.7832(2) 0.0215(9) Uani 1 1 d . . . . .
C23 C 0.4195(3) 0.3451(11) 0.7911(3) 0.0243(9) Uani 1 1 d . . . . .
H23 H 0.4680 0.3946 0.7544 0.029 Uiso 1 1 calc R . . . .
C24 C 0.4390(3) 0.1541(10) 0.8514(3) 0.0286(10) Uani 1 1 d . . . . .
H24 H 0.5012 0.0752 0.8555 0.034 Uiso 1 1 calc R . . . .
C25 C 0.3679(3) 0.0696(11) 0.9088(2) 0.0255(9) Uani 1 1 d . . . . .
C26 C 0.3871(3) -0.1331(12) 0.9719(2) 0.0307(10) Uani 1 1 d . . . . .
H26 H 0.4488 -0.2149 0.9768 0.037 Uiso 1 1 calc R . . . .
C27 C 0.3158(4) -0.2101(11) 1.0260(3) 0.0330(11) Uani 1 1 d . . . . .
H27 H 0.3301 -0.3420 1.0673 0.040 Uiso 1 1 calc R . . . .
C28 C 0.2224(4) -0.0931(11) 1.0199(3) 0.0314(10) Uani 1 1 d . . . . .
H28 H 0.1747 -0.1498 1.0565 0.038 Uiso 1 1 calc R . . . .
C29 C 0.2002(3) 0.1081(11) 0.9591(2) 0.0268(10) Uani 1 1 d . . . . .
C30 C 0.1043(3) 0.2348(13) 0.9501(3) 0.0320(10) Uani 1 1 d . . . . .
H30 H 0.0553 0.1790 0.9856 0.038 Uiso 1 1 calc R . . . .
C31 C 0.0846(3) 0.4310(12) 0.8917(3) 0.0311(11) Uani 1 1 d . . . . .
H31 H 0.0224 0.5104 0.8883 0.037 Uiso 1 1 calc R . . . .
C32 C 0.1569(3) 0.5213(10) 0.8343(3) 0.0242(9) Uani 1 1 d . . . . .
C33 C 0.1378(3) 0.7292(11) 0.7739(2) 0.0261(9) Uani 1 1 d . . . . .
H33 H 0.0769 0.8174 0.7711 0.031 Uiso 1 1 calc R . . . .
C34 C 0.2091(3) 0.8053(11) 0.7179(2) 0.0262(9) Uani 1 1 d . . . . .
H34 H 0.1955 0.9415 0.6774 0.031 Uiso 1 1 calc R . . . .
C35 C 0.2518(3) 0.3989(10) 0.8405(2) 0.0192(8) Uani 1 1 d . . . . .
C36 C 0.2730(3) 0.1920(11) 0.9025(2) 0.0222(9) Uani 1 1 d . . . . .
H1 H 0.648(3) 0.900(6) 0.411(2) 0.018(11) Uiso 1 1 d D . . . .
H2 H 0.357(6) 0.883(12) 0.638(4) 0.09(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.396(5) . ?
C1 C2 1.384(6) . ?
C1 C14 1.386(6) . ?
C2 C3 1.445(6) . ?
C2 C15 1.420(5) . ?
C3 C4 1.365(6) . ?
C4 C5 1.424(6) . ?
C5 C6 1.402(6) . ?
C5 C16 1.424(6) . ?
C6 C7 1.385(7) . ?
C7 C8 1.384(9) . ?
C8 C9 1.386(7) . ?
C9 C10 1.439(6) . ?
C9 C16 1.434(6) . ?
C10 C11 1.350(7) . ?
C11 C12 1.433(6) . ?
C12 C13 1.396(7) . ?
C12 C15 1.424(5) . ?
C13 C14 1.391(6) . ?
C15 C16 1.424(6) . ?
O2 C21 1.376(5) . ?
C21 C22 1.401(7) . ?
C21 C34 1.389(6) . ?
C22 C23 1.445(6) . ?
C22 C35 1.413(6) . ?
C23 C24 1.349(7) . ?
C24 C25 1.417(6) . ?
C25 C26 1.418(7) . ?
C25 C36 1.423(6) . ?
C26 C27 1.374(7) . ?
C27 C28 1.396(7) . ?
C28 C29 1.392(7) . ?
C29 C30 1.448(7) . ?
C29 C36 1.424(6) . ?
C30 C31 1.343(7) . ?
C31 C32 1.436(6) . ?
C32 C33 1.401(6) . ?
C32 C35 1.423(5) . ?
C33 C34 1.394(6) . ?
C35 C36 1.422(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 116.0(4) . . ?
C2 C1 C14 121.9(4) . . ?
C14 C1 O1 121.8(4) . . ?
C1 C2 C3 122.4(4) . . ?
C1 C2 C15 118.6(4) . . ?
C15 C2 C3 119.1(4) . . ?
C4 C3 C2 120.2(4) . . ?
C3 C4 C5 122.0(4) . . ?
C4 C5 C16 118.6(4) . . ?
C6 C5 C4 123.0(4) . . ?
C6 C5 C16 118.3(4) . . ?
C7 C6 C5 120.9(5) . . ?
C8 C7 C6 121.1(5) . . ?
C7 C8 C9 120.4(5) . . ?
C8 C9 C10 122.8(4) . . ?
C8 C9 C16 119.3(4) . . ?
C16 C9 C10 117.9(4) . . ?
C11 C10 C9 121.9(4) . . ?
C10 C11 C12 121.4(4) . . ?
C13 C12 C11 122.4(4) . . ?
C13 C12 C15 119.1(4) . . ?
C15 C12 C11 118.5(4) . . ?
C14 C13 C12 120.6(4) . . ?
C1 C14 C13 119.8(4) . . ?
C2 C15 C12 119.9(4) . . ?
C2 C15 C16 119.8(4) . . ?
C12 C15 C16 120.2(4) . . ?
C5 C16 C9 119.8(4) . . ?
C5 C16 C15 120.2(3) . . ?
C15 C16 C9 120.0(4) . . ?
O2 C21 C22 117.2(4) . . ?
O2 C21 C34 121.0(4) . . ?
C34 C21 C22 121.7(4) . . ?
C21 C22 C23 122.7(4) . . ?
C21 C22 C35 118.5(4) . . ?
C35 C22 C23 118.9(4) . . ?
C24 C23 C22 120.5(4) . . ?
C23 C24 C25 122.2(4) . . ?
C24 C25 C26 122.7(4) . . ?
C24 C25 C36 118.7(4) . . ?
C26 C25 C36 118.6(4) . . ?
C27 C26 C25 120.8(5) . . ?
C26 C27 C28 121.0(5) . . ?
C29 C28 C27 120.3(5) . . ?
C28 C29 C30 122.3(4) . . ?
C28 C29 C36 119.8(5) . . ?
C36 C29 C30 117.9(4) . . ?
C31 C30 C29 121.5(4) . . ?
C30 C31 C32 121.7(4) . . ?
C33 C32 C31 122.3(4) . . ?
C33 C32 C35 119.1(4) . . ?
C35 C32 C31 118.6(4) . . ?
C34 C33 C32 120.6(4) . . ?
C21 C34 C33 119.8(4) . . ?
C22 C35 C32 120.2(4) . . ?
C22 C35 C36 119.9(3) . . ?
C36 C35 C32 119.8(4) . . ?
C25 C36 C29 119.5(4) . . ?
C35 C36 C25 119.9(4) . . ?
C35 C36 C29 120.5(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.453(3)
2 0.547(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_t240
_database_code_depnum_ccdc_archive 'CCDC 1892305'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8327(7)
_cell_length_b                   4.56126(18)
_cell_length_c                   16.6307(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.013(4)
_cell_angle_gamma                90
_cell_volume                     1049.30(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3586
_cell_measurement_temperature    239.98(10)
_cell_measurement_theta_max      75.9540
_cell_measurement_theta_min      4.1370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6257
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         2.657
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      239.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1010889000
_diffrn_orient_matrix_UB_12      -0.1409711000
_diffrn_orient_matrix_UB_13      0.0035408000
_diffrn_orient_matrix_UB_21      0.0001722000
_diffrn_orient_matrix_UB_22      -0.0302321000
_diffrn_orient_matrix_UB_23      -0.0922962000
_diffrn_orient_matrix_UB_31      0.0467398000
_diffrn_orient_matrix_UB_32      0.3053062000
_diffrn_orient_matrix_UB_33      -0.0074547000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.522
_reflns_Friedel_fraction_full    0.678
_reflns_Friedel_fraction_max     0.685
_reflns_number_gt                2884
_reflns_number_total             3054
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.543(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3054
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.050
_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)+(0.0830P)²+0.1138P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1293
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.457(3)
 0.543(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6422(3) 0.7244(9) 0.42732(19) 0.0447(8) Uani 1 1 d D . . . .
C1 C 0.7182(3) 0.6828(12) 0.4810(3) 0.0348(10) Uani 1 1 d . . . . .
C2 C 0.7021(3) 0.4875(12) 0.5434(3) 0.0315(10) Uani 1 1 d . . . . .
C3 C 0.6088(3) 0.3454(12) 0.5546(3) 0.0372(11) Uani 1 1 d . . . . .
H3 H 0.5582 0.3842 0.5193 0.045 Uiso 1 1 calc R . . . .
C4 C 0.5957(4) 0.1557(13) 0.6168(3) 0.0406(12) Uani 1 1 d . . . . .
H4 H 0.5353 0.0690 0.6235 0.049 Uiso 1 1 calc R . . . .
C5 C 0.6710(4) 0.0848(11) 0.6720(3) 0.0395(11) Uani 1 1 d . . . . .
C6 C 0.6590(5) -0.1119(14) 0.7361(3) 0.0538(14) Uani 1 1 d . . . . .
H6 H 0.6000 -0.2058 0.7434 0.065 Uiso 1 1 calc R . . . .
C7 C 0.7351(6) -0.1669(18) 0.7887(3) 0.0660(19) Uani 1 1 d . . . . .
H7 H 0.7263 -0.2984 0.8308 0.079 Uiso 1 1 calc R . . . .
C8 C 0.8233(6) -0.0302(16) 0.7796(4) 0.0639(19) Uani 1 1 d . . . . .
H8 H 0.8722 -0.0660 0.8167 0.077 Uiso 1 1 calc R . . . .
C9 C 0.8400(4) 0.1585(13) 0.7166(3) 0.0462(13) Uani 1 1 d . . . . .
C10 C 0.9310(4) 0.3003(15) 0.7037(3) 0.0507(14) Uani 1 1 d . . . . .
H10 H 0.9817 0.2626 0.7389 0.061 Uiso 1 1 calc R . . . .
C11 C 0.9453(4) 0.4868(15) 0.6421(3) 0.0512(14) Uani 1 1 d . . . . .
H11 H 1.0058 0.5726 0.6357 0.061 Uiso 1 1 calc R . . . .
C12 C 0.8699(3) 0.5569(12) 0.5862(3) 0.0378(10) Uani 1 1 d . . . . .
C13 C 0.8822(3) 0.7542(14) 0.5232(3) 0.0437(12) Uani 1 1 d . . . . .
H13 H 0.9416 0.8463 0.5164 0.052 Uiso 1 1 calc R . . . .
C14 C 0.8075(4) 0.8155(13) 0.4706(3) 0.0431(12) Uani 1 1 d . . . . .
H14 H 0.8171 0.9455 0.4283 0.052 Uiso 1 1 calc R . . . .
C15 C 0.7783(3) 0.4217(12) 0.5969(3) 0.0321(10) Uani 1 1 d . . . . .
C16 C 0.7624(3) 0.2247(13) 0.6619(3) 0.0348(10) Uani 1 1 d . . . . .
O2 O 0.3691(3) 0.7265(9) 0.6647(2) 0.0467(8) Uani 1 1 d D . . . .
C21 C 0.3004(3) 0.6747(12) 0.7224(3) 0.0356(10) Uani 1 1 d . . . . .
C22 C 0.3240(3) 0.4732(11) 0.7828(3) 0.0328(10) Uani 1 1 d . . . . .
C23 C 0.4184(3) 0.3457(12) 0.7906(3) 0.0381(11) Uani 1 1 d . . . . .
H23 H 0.4665 0.3951 0.7539 0.046 Uiso 1 1 calc R . . . .
C24 C 0.4382(3) 0.1553(12) 0.8503(3) 0.0435(12) Uani 1 1 d . . . . .
H24 H 0.5000 0.0760 0.8539 0.052 Uiso 1 1 calc R . . . .
C25 C 0.3680(4) 0.0720(12) 0.9079(3) 0.0399(11) Uani 1 1 d . . . . .
C26 C 0.3868(4) -0.1283(15) 0.9711(3) 0.0501(14) Uani 1 1 d . . . . .
H26 H 0.4478 -0.2116 0.9760 0.060 Uiso 1 1 calc R . . . .
C27 C 0.3155(5) -0.2007(14) 1.0253(3) 0.0545(15) Uani 1 1 d . . . . .
H27 H 0.3294 -0.3312 1.0667 0.065 Uiso 1 1 calc R . . . .
C28 C 0.2234(5) -0.0834(14) 1.0196(3) 0.0524(15) Uani 1 1 d . . . . .
H28 H 0.1763 -0.1384 1.0565 0.063 Uiso 1 1 calc R . . . .
C29 C 0.2006(4) 0.1161(13) 0.9591(3) 0.0433(12) Uani 1 1 d . . . . .
C30 C 0.1065(4) 0.2420(17) 0.9501(3) 0.0519(14) Uani 1 1 d . . . . .
H30 H 0.0577 0.1875 0.9855 0.062 Uiso 1 1 calc R . . . .
C31 C 0.0868(4) 0.4354(16) 0.8921(3) 0.0502(15) Uani 1 1 d . . . . .
H31 H 0.0250 0.5154 0.8892 0.060 Uiso 1 1 calc R . . . .
C32 C 0.1577(3) 0.5236(12) 0.8344(3) 0.0386(11) Uani 1 1 d . . . . .
C33 C 0.1389(3) 0.7273(14) 0.7742(3) 0.0436(11) Uani 1 1 d . . . . .
H33 H 0.0783 0.8153 0.7715 0.052 Uiso 1 1 calc R . . . .
C34 C 0.2098(4) 0.8022(12) 0.7177(3) 0.0406(11) Uani 1 1 d . . . . .
H34 H 0.1960 0.9367 0.6773 0.049 Uiso 1 1 calc R . . . .
C35 C 0.2521(3) 0.3998(12) 0.8403(3) 0.0319(10) Uani 1 1 d . . . . .
C36 C 0.2738(3) 0.1972(12) 0.9021(3) 0.0338(10) Uani 1 1 d . . . . .
H1 H 0.652(5) 0.894(7) 0.410(3) 0.059(19) Uiso 1 1 d D . . . .
H2 H 0.362(6) 0.874(12) 0.635(4) 0.11(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.392(5) . ?
C1 C2 1.386(7) . ?
C1 C14 1.387(7) . ?
C2 C3 1.456(6) . ?
C2 C15 1.412(6) . ?
C3 C4 1.360(7) . ?
C4 C5 1.426(7) . ?
C5 C6 1.403(7) . ?
C5 C16 1.427(7) . ?
C6 C7 1.391(9) . ?
C7 C8 1.378(11) . ?
C8 C9 1.376(9) . ?
C9 C10 1.431(8) . ?
C9 C16 1.439(6) . ?
C10 C11 1.346(9) . ?
C11 C12 1.433(7) . ?
C12 C13 1.392(8) . ?
C12 C15 1.420(6) . ?
C13 C14 1.383(7) . ?
C15 C16 1.423(7) . ?
O2 C21 1.372(5) . ?
C21 C22 1.400(7) . ?
C21 C34 1.383(7) . ?
C22 C23 1.436(7) . ?
C22 C35 1.420(6) . ?
C23 C24 1.348(8) . ?
C24 C25 1.416(7) . ?
C25 C26 1.417(8) . ?
C25 C36 1.426(7) . ?
C26 C27 1.377(8) . ?
C27 C28 1.385(9) . ?
C28 C29 1.392(8) . ?
C29 C30 1.431(9) . ?
C29 C36 1.436(6) . ?
C30 C31 1.335(9) . ?
C31 C32 1.430(7) . ?
C32 C33 1.391(8) . ?
C32 C35 1.426(6) . ?
C33 C34 1.401(7) . ?
C35 C36 1.413(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 116.5(4) . . ?
C2 C1 C14 121.2(4) . . ?
C14 C1 O1 122.2(5) . . ?
C1 C2 C3 121.7(4) . . ?
C1 C2 C15 119.2(4) . . ?
C15 C2 C3 119.1(4) . . ?
C4 C3 C2 119.9(4) . . ?
C3 C4 C5 122.4(5) . . ?
C4 C5 C16 118.1(4) . . ?
C6 C5 C4 123.2(5) . . ?
C6 C5 C16 118.7(5) . . ?
C7 C6 C5 120.2(6) . . ?
C8 C7 C6 121.3(6) . . ?
C9 C8 C7 121.0(6) . . ?
C8 C9 C10 123.0(5) . . ?
C8 C9 C16 119.1(6) . . ?
C10 C9 C16 117.8(5) . . ?
C11 C10 C9 121.9(4) . . ?
C10 C11 C12 121.8(5) . . ?
C13 C12 C11 122.9(5) . . ?
C13 C12 C15 119.0(4) . . ?
C15 C12 C11 118.1(5) . . ?
C14 C13 C12 121.0(5) . . ?
C13 C14 C1 119.9(5) . . ?
C2 C15 C12 119.7(4) . . ?
C2 C15 C16 119.8(4) . . ?
C12 C15 C16 120.5(4) . . ?
C5 C16 C9 119.5(5) . . ?
C15 C16 C5 120.6(4) . . ?
C15 C16 C9 119.8(5) . . ?
O2 C21 C22 116.9(4) . . ?
O2 C21 C34 121.1(4) . . ?
C34 C21 C22 121.8(4) . . ?
C21 C22 C23 122.9(4) . . ?
C21 C22 C35 118.4(4) . . ?
C35 C22 C23 118.7(4) . . ?
C24 C23 C22 120.8(4) . . ?
C23 C24 C25 122.1(5) . . ?
C24 C25 C26 123.3(5) . . ?
C24 C25 C36 118.3(4) . . ?
C26 C25 C36 118.4(5) . . ?
C27 C26 C25 120.7(6) . . ?
C26 C27 C28 121.4(6) . . ?
C27 C28 C29 120.7(6) . . ?
C28 C29 C30 122.9(5) . . ?
C28 C29 C36 119.1(6) . . ?
C30 C29 C36 117.9(5) . . ?
C31 C30 C29 121.8(5) . . ?
C30 C31 C32 122.0(5) . . ?
C33 C32 C31 122.9(5) . . ?
C33 C32 C35 119.1(4) . . ?
C35 C32 C31 118.1(5) . . ?
C32 C33 C34 121.0(5) . . ?
C21 C34 C33 119.6(5) . . ?
C22 C35 C32 120.1(5) . . ?
C36 C35 C22 119.7(4) . . ?
C36 C35 C32 120.2(4) . . ?
C25 C36 C29 119.7(5) . . ?
C35 C36 C25 120.3(4) . . ?
C35 C36 C29 119.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.457(3)
2 0.543(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_t110
_database_code_depnum_ccdc_archive 'CCDC 1892312'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7570(5)
_cell_length_b                   4.53004(14)
_cell_length_c                   16.5589(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.965(3)
_cell_angle_gamma                90
_cell_volume                     1031.94(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4288
_cell_measurement_temperature    110.02(12)
_cell_measurement_theta_max      75.9440
_cell_measurement_theta_min      4.1490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6106
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.051
_diffrn_reflns_theta_min         2.668
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.02(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1016825000
_diffrn_orient_matrix_UB_12      -0.1409323000
_diffrn_orient_matrix_UB_13      0.0045492000
_diffrn_orient_matrix_UB_21      0.0009394000
_diffrn_orient_matrix_UB_22      -0.0342461000
_diffrn_orient_matrix_UB_23      -0.0926163000
_diffrn_orient_matrix_UB_31      0.0467603000
_diffrn_orient_matrix_UB_32      0.3076042000
_diffrn_orient_matrix_UB_33      -0.0081489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.506
_reflns_Friedel_fraction_full    0.659
_reflns_Friedel_fraction_max     0.666
_reflns_number_gt                2946
_reflns_number_total             2988
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.546(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.041
_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)+(0.0974P)²+0.0655P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1252
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.454(3)
 0.546(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6405(2) 0.7295(8) 0.42700(17) 0.0239(6) Uani 1 1 d D . . . .
C1 C 0.7172(3) 0.6886(10) 0.4806(2) 0.0173(9) Uani 1 1 d . . . . .
C2 C 0.7008(3) 0.4897(10) 0.5430(2) 0.0166(9) Uani 1 1 d . . . . .
C3 C 0.6076(3) 0.3494(11) 0.5552(2) 0.0194(9) Uani 1 1 d . . . . .
H3 H 0.5562 0.3908 0.5205 0.023 Uiso 1 1 calc R . . . .
C4 C 0.5949(3) 0.1563(10) 0.6175(2) 0.0212(9) Uani 1 1 d . . . . .
H4 H 0.5345 0.0681 0.6246 0.025 Uiso 1 1 calc R . . . .
C5 C 0.6716(3) 0.0855(10) 0.6722(2) 0.0206(9) Uani 1 1 d . . . . .
C6 C 0.6600(3) -0.1130(12) 0.7370(3) 0.0277(10) Uani 1 1 d . . . . .
H6 H 0.6004 -0.2056 0.7447 0.033 Uiso 1 1 calc R . . . .
C7 C 0.7358(4) -0.1722(13) 0.7891(3) 0.0319(11) Uani 1 1 d . . . . .
H7 H 0.7268 -0.3057 0.8311 0.038 Uiso 1 1 calc R . . . .
C8 C 0.8256(4) -0.0342(12) 0.7796(3) 0.0317(12) Uani 1 1 d . . . . .
H8 H 0.8753 -0.0718 0.8162 0.038 Uiso 1 1 calc R . . . .
C9 C 0.8416(3) 0.1583(10) 0.7160(2) 0.0235(9) Uani 1 1 d . . . . .
C10 C 0.9333(3) 0.3024(11) 0.7027(3) 0.0251(10) Uani 1 1 d . . . . .
H10 H 0.9845 0.2640 0.7378 0.030 Uiso 1 1 calc R . . . .
C11 C 0.9472(3) 0.4915(12) 0.6409(3) 0.0239(10) Uani 1 1 d . . . . .
H11 H 1.0079 0.5786 0.6340 0.029 Uiso 1 1 calc R . . . .
C12 C 0.8706(3) 0.5609(10) 0.5856(2) 0.0192(9) Uani 1 1 d . . . . .
C13 C 0.8827(3) 0.7608(11) 0.5221(3) 0.0211(9) Uani 1 1 d . . . . .
H13 H 0.9424 0.8540 0.5151 0.025 Uiso 1 1 calc R . . . .
C14 C 0.8068(3) 0.8224(10) 0.4692(3) 0.0205(9) Uani 1 1 d . . . . .
H14 H 0.8161 0.9525 0.4265 0.025 Uiso 1 1 calc R . . . .
C15 C 0.7784(3) 0.4225(11) 0.5967(2) 0.0160(9) Uani 1 1 d . . . . .
C16 C 0.7631(3) 0.2249(12) 0.6615(2) 0.0192(9) Uani 1 1 d . . . . .
O2 O 0.3701(2) 0.7321(8) 0.66469(17) 0.0253(7) Uani 1 1 d D . . . .
C21 C 0.3006(3) 0.6780(10) 0.7224(2) 0.0180(9) Uani 1 1 d . . . . .
C22 C 0.3240(3) 0.4739(10) 0.7832(2) 0.0176(9) Uani 1 1 d . . . . .
C23 C 0.4197(3) 0.3460(11) 0.7910(3) 0.0199(9) Uani 1 1 d . . . . .
H23 H 0.4682 0.3959 0.7543 0.024 Uiso 1 1 calc R . . . .
C24 C 0.4391(3) 0.1540(10) 0.8514(3) 0.0231(10) Uani 1 1 d . . . . .
H24 H 0.5014 0.0753 0.8553 0.028 Uiso 1 1 calc R . . . .
C25 C 0.3682(3) 0.0684(10) 0.9087(2) 0.0204(9) Uani 1 1 d . . . . .
C26 C 0.3868(3) -0.1340(12) 0.9720(2) 0.0244(10) Uani 1 1 d . . . . .
H26 H 0.4485 -0.2159 0.9770 0.029 Uiso 1 1 calc R . . . .
C27 C 0.3158(3) -0.2114(11) 1.0259(3) 0.0277(10) Uani 1 1 d . . . . .
H27 H 0.3300 -0.3438 1.0672 0.033 Uiso 1 1 calc R . . . .
C28 C 0.2219(4) -0.0939(11) 1.0199(3) 0.0264(10) Uani 1 1 d . . . . .
H28 H 0.1741 -0.1503 1.0565 0.032 Uiso 1 1 calc R . . . .
C29 C 0.2002(3) 0.1067(11) 0.9591(2) 0.0220(10) Uani 1 1 d . . . . .
C30 C 0.1040(3) 0.2351(13) 0.9501(3) 0.0267(10) Uani 1 1 d . . . . .
H30 H 0.0550 0.1807 0.9859 0.032 Uiso 1 1 calc R . . . .
C31 C 0.0844(3) 0.4294(12) 0.8918(3) 0.0268(11) Uani 1 1 d . . . . .
H31 H 0.0220 0.5077 0.8882 0.032 Uiso 1 1 calc R . . . .
C32 C 0.1565(3) 0.5212(10) 0.8342(3) 0.0200(9) Uani 1 1 d . . . . .
C33 C 0.1374(3) 0.7282(11) 0.7739(2) 0.0215(9) Uani 1 1 d . . . . .
H33 H 0.0764 0.8161 0.7710 0.026 Uiso 1 1 calc R . . . .
C34 C 0.2090(3) 0.8048(11) 0.7179(2) 0.0218(9) Uani 1 1 d . . . . .
H34 H 0.1953 0.9412 0.6775 0.026 Uiso 1 1 calc R . . . .
C35 C 0.2518(3) 0.3980(10) 0.8402(2) 0.0151(8) Uani 1 1 d . . . . .
C36 C 0.2728(3) 0.1921(11) 0.9025(2) 0.0184(9) Uani 1 1 d . . . . .
H1 H 0.647(3) 0.901(6) 0.411(2) 0.013(11) Uiso 1 1 d D . . . .
H2 H 0.364(6) 0.892(11) 0.640(5) 0.10(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.392(5) . ?
C1 C2 1.390(6) . ?
C1 C14 1.385(6) . ?
C2 C3 1.446(6) . ?
C2 C15 1.421(5) . ?
C3 C4 1.363(6) . ?
C4 C5 1.427(6) . ?
C5 C6 1.409(6) . ?
C5 C16 1.420(6) . ?
C6 C7 1.380(7) . ?
C7 C8 1.394(8) . ?
C8 C9 1.384(7) . ?
C9 C10 1.436(6) . ?
C9 C16 1.440(6) . ?
C10 C11 1.349(7) . ?
C11 C12 1.432(6) . ?
C12 C13 1.397(7) . ?
C12 C15 1.427(5) . ?
C13 C14 1.392(6) . ?
C15 C16 1.413(6) . ?
O2 C21 1.373(5) . ?
C21 C22 1.404(7) . ?
C21 C34 1.387(6) . ?
C22 C23 1.445(6) . ?
C22 C35 1.412(6) . ?
C23 C24 1.352(7) . ?
C24 C25 1.415(6) . ?
C25 C26 1.415(7) . ?
C25 C36 1.432(6) . ?
C26 C27 1.370(7) . ?
C27 C28 1.400(7) . ?
C28 C29 1.388(7) . ?
C29 C30 1.453(6) . ?
C29 C36 1.422(6) . ?
C30 C31 1.335(7) . ?
C31 C32 1.437(6) . ?
C32 C33 1.395(6) . ?
C32 C35 1.428(5) . ?
C33 C34 1.397(6) . ?
C35 C36 1.421(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 116.0(4) . . ?
C14 C1 O1 122.0(4) . . ?
C14 C1 C2 121.9(4) . . ?
C1 C2 C3 122.2(4) . . ?
C1 C2 C15 118.8(4) . . ?
C15 C2 C3 119.0(4) . . ?
C4 C3 C2 120.0(4) . . ?
C3 C4 C5 122.0(4) . . ?
C6 C5 C4 122.9(4) . . ?
C6 C5 C16 118.6(4) . . ?
C16 C5 C4 118.5(4) . . ?
C7 C6 C5 121.0(5) . . ?
C6 C7 C8 120.8(5) . . ?
C9 C8 C7 120.6(5) . . ?
C8 C9 C10 122.8(4) . . ?
C8 C9 C16 119.3(4) . . ?
C10 C9 C16 117.9(4) . . ?
C11 C10 C9 122.0(4) . . ?
C10 C11 C12 121.4(4) . . ?
C13 C12 C11 122.4(4) . . ?
C13 C12 C15 119.2(4) . . ?
C15 C12 C11 118.5(4) . . ?
C14 C13 C12 120.9(4) . . ?
C1 C14 C13 119.6(4) . . ?
C2 C15 C12 119.5(4) . . ?
C16 C15 C2 120.0(4) . . ?
C16 C15 C12 120.5(4) . . ?
C5 C16 C9 119.6(4) . . ?
C15 C16 C5 120.5(3) . . ?
C15 C16 C9 119.9(4) . . ?
O2 C21 C22 117.2(4) . . ?
O2 C21 C34 121.4(4) . . ?
C34 C21 C22 121.3(4) . . ?
C21 C22 C23 122.5(4) . . ?
C21 C22 C35 118.5(4) . . ?
C35 C22 C23 118.9(4) . . ?
C24 C23 C22 120.3(4) . . ?
C23 C24 C25 122.4(4) . . ?
C24 C25 C36 118.5(4) . . ?
C26 C25 C24 123.3(4) . . ?
C26 C25 C36 118.2(4) . . ?
C27 C26 C25 121.3(4) . . ?
C26 C27 C28 120.9(5) . . ?
C29 C28 C27 120.0(4) . . ?
C28 C29 C30 122.2(4) . . ?
C28 C29 C36 120.3(5) . . ?
C36 C29 C30 117.5(4) . . ?
C31 C30 C29 121.5(4) . . ?
C30 C31 C32 122.1(4) . . ?
C33 C32 C31 122.6(4) . . ?
C33 C32 C35 119.0(4) . . ?
C35 C32 C31 118.3(4) . . ?
C32 C33 C34 120.6(4) . . ?
C21 C34 C33 120.1(4) . . ?
C22 C35 C32 120.3(4) . . ?
C22 C35 C36 120.1(3) . . ?
C36 C35 C32 119.6(4) . . ?
C29 C36 C25 119.3(4) . . ?
C35 C36 C25 119.7(4) . . ?
C35 C36 C29 121.0(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.454(3)
2 0.546(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_t120
_database_code_depnum_ccdc_archive 'CCDC 1892313'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7629(5)
_cell_length_b                   4.53229(13)
_cell_length_c                   16.5628(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.962(3)
_cell_angle_gamma                90
_cell_volume                     1033.15(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4278
_cell_measurement_temperature    122(3)
_cell_measurement_theta_max      74.6350
_cell_measurement_theta_min      4.1480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6101
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.007
_diffrn_reflns_theta_min         2.668
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1016380000
_diffrn_orient_matrix_UB_12      -0.1410389000
_diffrn_orient_matrix_UB_13      0.0043773000
_diffrn_orient_matrix_UB_21      0.0007678000
_diffrn_orient_matrix_UB_22      -0.0338345000
_diffrn_orient_matrix_UB_23      -0.0925939000
_diffrn_orient_matrix_UB_31      0.0467805000
_diffrn_orient_matrix_UB_32      0.3074105000
_diffrn_orient_matrix_UB_33      -0.0081086000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.506
_reflns_Friedel_fraction_full    0.659
_reflns_Friedel_fraction_max     0.667
_reflns_number_gt                2932
_reflns_number_total             2989
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.545(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2989
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0957P)²+0.1016P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1263
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.455(3)
 0.545(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6406(2) 0.7294(8) 0.42711(17) 0.0270(6) Uani 1 1 d D . . . .
C1 C 0.7171(3) 0.6882(11) 0.4807(2) 0.0217(9) Uani 1 1 d . . . . .
C2 C 0.7006(3) 0.4893(10) 0.5432(2) 0.0192(9) Uani 1 1 d . . . . .
C3 C 0.6075(3) 0.3484(11) 0.5552(2) 0.0219(9) Uani 1 1 d . . . . .
H3 H 0.5562 0.3888 0.5203 0.026 Uiso 1 1 calc R . . . .
C4 C 0.5950(3) 0.1563(11) 0.6176(3) 0.0244(10) Uani 1 1 d . . . . .
H4 H 0.5345 0.0688 0.6248 0.029 Uiso 1 1 calc R . . . .
C5 C 0.6715(3) 0.0850(11) 0.6721(2) 0.0236(9) Uani 1 1 d . . . . .
C6 C 0.6597(4) -0.1122(13) 0.7369(3) 0.0325(10) Uani 1 1 d . . . . .
H6 H 0.6000 -0.2040 0.7448 0.039 Uiso 1 1 calc R . . . .
C7 C 0.7359(4) -0.1721(14) 0.7892(3) 0.0362(12) Uani 1 1 d . . . . .
H7 H 0.7269 -0.3062 0.8311 0.043 Uiso 1 1 calc R . . . .
C8 C 0.8253(4) -0.0343(13) 0.7798(3) 0.0358(12) Uani 1 1 d . . . . .
H8 H 0.8747 -0.0715 0.8167 0.043 Uiso 1 1 calc R . . . .
C9 C 0.8417(3) 0.1583(11) 0.7161(3) 0.0275(10) Uani 1 1 d . . . . .
C10 C 0.9334(3) 0.3022(12) 0.7028(3) 0.0291(11) Uani 1 1 d . . . . .
H10 H 0.9846 0.2641 0.7379 0.035 Uiso 1 1 calc R . . . .
C11 C 0.9471(3) 0.4908(12) 0.6410(3) 0.0281(10) Uani 1 1 d . . . . .
H11 H 1.0078 0.5775 0.6339 0.034 Uiso 1 1 calc R . . . .
C12 C 0.8703(3) 0.5610(11) 0.5857(2) 0.0224(9) Uani 1 1 d . . . . .
C13 C 0.8826(3) 0.7605(11) 0.5223(3) 0.0247(10) Uani 1 1 d . . . . .
H13 H 0.9423 0.8538 0.5154 0.030 Uiso 1 1 calc R . . . .
C14 C 0.8069(3) 0.8216(11) 0.4695(3) 0.0241(10) Uani 1 1 d . . . . .
H14 H 0.8164 0.9514 0.4267 0.029 Uiso 1 1 calc R . . . .
C15 C 0.7784(3) 0.4229(11) 0.5966(2) 0.0196(9) Uani 1 1 d . . . . .
C16 C 0.7631(3) 0.2246(12) 0.6615(2) 0.0223(9) Uani 1 1 d . . . . .
O2 O 0.3701(2) 0.7321(9) 0.66478(18) 0.0283(7) Uani 1 1 d D . . . .
C21 C 0.3005(3) 0.6777(10) 0.7227(2) 0.0212(9) Uani 1 1 d . . . . .
C22 C 0.3240(3) 0.4742(10) 0.7831(3) 0.0199(9) Uani 1 1 d . . . . .
C23 C 0.4196(3) 0.3461(11) 0.7911(3) 0.0226(9) Uani 1 1 d . . . . .
H23 H 0.4681 0.3964 0.7545 0.027 Uiso 1 1 calc R . . . .
C24 C 0.4393(3) 0.1539(10) 0.8513(3) 0.0266(10) Uani 1 1 d . . . . .
H24 H 0.5014 0.0746 0.8551 0.032 Uiso 1 1 calc R . . . .
C25 C 0.3681(3) 0.0690(11) 0.9090(3) 0.0235(9) Uani 1 1 d . . . . .
C26 C 0.3868(3) -0.1342(12) 0.9721(3) 0.0284(10) Uani 1 1 d . . . . .
H26 H 0.4483 -0.2173 0.9769 0.034 Uiso 1 1 calc R . . . .
C27 C 0.3156(4) -0.2103(12) 1.0262(3) 0.0315(11) Uani 1 1 d . . . . .
H27 H 0.3297 -0.3418 1.0677 0.038 Uiso 1 1 calc R . . . .
C28 C 0.2222(4) -0.0929(12) 1.0198(3) 0.0289(11) Uani 1 1 d . . . . .
H28 H 0.1744 -0.1488 1.0565 0.035 Uiso 1 1 calc R . . . .
C29 C 0.2004(3) 0.1069(12) 0.9591(3) 0.0252(10) Uani 1 1 d . . . . .
C30 C 0.1043(3) 0.2339(14) 0.9502(3) 0.0300(10) Uani 1 1 d . . . . .
H30 H 0.0552 0.1781 0.9857 0.036 Uiso 1 1 calc R . . . .
C31 C 0.0847(3) 0.4303(12) 0.8918(3) 0.0297(11) Uani 1 1 d . . . . .
H31 H 0.0226 0.5100 0.8886 0.036 Uiso 1 1 calc R . . . .
C32 C 0.1567(3) 0.5212(11) 0.8342(3) 0.0231(9) Uani 1 1 d . . . . .
C33 C 0.1377(3) 0.7285(11) 0.7740(2) 0.0239(9) Uani 1 1 d . . . . .
H33 H 0.0769 0.8170 0.7713 0.029 Uiso 1 1 calc R . . . .
C34 C 0.2091(3) 0.8048(11) 0.7177(3) 0.0247(10) Uani 1 1 d . . . . .
H34 H 0.1953 0.9400 0.6770 0.030 Uiso 1 1 calc R . . . .
C35 C 0.2518(3) 0.3986(10) 0.8402(2) 0.0184(9) Uani 1 1 d . . . . .
C36 C 0.2728(3) 0.1920(11) 0.9024(2) 0.0206(9) Uani 1 1 d . . . . .
H1 H 0.647(3) 0.899(6) 0.409(2) 0.010(10) Uiso 1 1 d D . . . .
H2 H 0.362(6) 0.888(11) 0.639(4) 0.08(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.390(5) . ?
C1 C2 1.391(7) . ?
C1 C14 1.389(6) . ?
C2 C3 1.446(6) . ?
C2 C15 1.420(5) . ?
C3 C4 1.362(6) . ?
C4 C5 1.426(6) . ?
C5 C6 1.405(7) . ?
C5 C16 1.422(7) . ?
C6 C7 1.387(7) . ?
C7 C8 1.388(9) . ?
C8 C9 1.388(7) . ?
C9 C10 1.438(6) . ?
C9 C16 1.441(6) . ?
C10 C11 1.347(7) . ?
C11 C12 1.435(6) . ?
C12 C13 1.396(7) . ?
C12 C15 1.423(6) . ?
C13 C14 1.389(6) . ?
C15 C16 1.417(7) . ?
O2 C21 1.378(5) . ?
C21 C22 1.398(7) . ?
C21 C34 1.387(6) . ?
C22 C23 1.445(6) . ?
C22 C35 1.413(6) . ?
C23 C24 1.352(7) . ?
C24 C25 1.421(6) . ?
C25 C26 1.416(7) . ?
C25 C36 1.429(6) . ?
C26 C27 1.373(7) . ?
C27 C28 1.394(8) . ?
C28 C29 1.387(7) . ?
C29 C30 1.450(7) . ?
C29 C36 1.423(6) . ?
C30 C31 1.341(8) . ?
C31 C32 1.435(6) . ?
C32 C33 1.395(6) . ?
C32 C35 1.426(6) . ?
C33 C34 1.398(6) . ?
C35 C36 1.422(6) . ?

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 C1 C2 116.0(4) . . ?
C14 C1 O1 122.1(4) . . ?
C14 C1 C2 121.8(4) . . ?
C1 C2 C3 122.2(4) . . ?
C1 C2 C15 118.6(4) . . ?
C15 C2 C3 119.3(4) . . ?
C4 C3 C2 119.9(4) . . ?
C3 C4 C5 122.2(4) . . ?
C6 C5 C4 122.9(4) . . ?
C6 C5 C16 118.6(4) . . ?
C16 C5 C4 118.4(4) . . ?
C7 C6 C5 121.0(5) . . ?
C6 C7 C8 120.8(5) . . ?
C7 C8 C9 120.8(5) . . ?
C8 C9 C10 123.0(4) . . ?
C8 C9 C16 119.1(5) . . ?
C10 C9 C16 117.9(4) . . ?
C11 C10 C9 121.8(4) . . ?
C10 C11 C12 121.5(4) . . ?
C13 C12 C11 122.3(4) . . ?
C13 C12 C15 119.2(4) . . ?
C15 C12 C11 118.5(4) . . ?
C14 C13 C12 120.8(4) . . ?
C1 C14 C13 119.8(4) . . ?
C2 C15 C12 119.9(4) . . ?
C16 C15 C2 119.7(4) . . ?
C16 C15 C12 120.4(4) . . ?
C5 C16 C9 119.7(4) . . ?
C15 C16 C5 120.5(4) . . ?
C15 C16 C9 119.8(4) . . ?
O2 C21 C22 117.1(4) . . ?
O2 C21 C34 120.9(4) . . ?
C34 C21 C22 121.8(4) . . ?
C21 C22 C23 122.8(4) . . ?
C21 C22 C35 118.4(4) . . ?
C35 C22 C23 118.7(4) . . ?
C24 C23 C22 120.6(4) . . ?
C23 C24 C25 122.2(4) . . ?
C24 C25 C36 118.3(4) . . ?
C26 C25 C24 123.1(4) . . ?
C26 C25 C36 118.6(4) . . ?
C27 C26 C25 121.0(5) . . ?
C26 C27 C28 120.8(5) . . ?
C29 C28 C27 120.3(5) . . ?
C28 C29 C30 122.1(4) . . ?
C28 C29 C36 120.2(5) . . ?
C36 C29 C30 117.7(4) . . ?
C31 C30 C29 121.3(4) . . ?
C30 C31 C32 122.1(4) . . ?
C33 C32 C31 122.7(4) . . ?
C33 C32 C35 118.9(4) . . ?
C35 C32 C31 118.4(4) . . ?
C32 C33 C34 120.8(4) . . ?
C21 C34 C33 119.6(4) . . ?
C22 C35 C32 120.3(4) . . ?
C22 C35 C36 120.1(4) . . ?
C36 C35 C32 119.6(4) . . ?
C29 C36 C25 119.1(4) . . ?
C35 C36 C25 120.0(4) . . ?
C35 C36 C29 120.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.455(3)
2 0.545(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_t280
_database_code_depnum_ccdc_archive 'CCDC 1892308'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8533(7)
_cell_length_b                   4.57352(16)
_cell_length_c                   16.6470(7)
_cell_angle_alpha                90
_cell_angle_beta                 89.994(4)
_cell_angle_gamma                90
_cell_volume                     1054.73(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3231
_cell_measurement_temperature    279.99(10)
_cell_measurement_theta_max      74.8270
_cell_measurement_theta_min      2.6530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6278
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.020
_diffrn_reflns_theta_min         2.654
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      279.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1009093000
_diffrn_orient_matrix_UB_12      -0.1407806000
_diffrn_orient_matrix_UB_13      0.0033810000
_diffrn_orient_matrix_UB_21      0.0001040000
_diffrn_orient_matrix_UB_22      -0.0292460000
_diffrn_orient_matrix_UB_23      -0.0922042000
_diffrn_orient_matrix_UB_31      0.0467096000
_diffrn_orient_matrix_UB_32      0.3046146000
_diffrn_orient_matrix_UB_33      -0.0072525000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.524
_reflns_Friedel_fraction_full    0.680
_reflns_Friedel_fraction_max     0.688
_reflns_number_gt                2811
_reflns_number_total             3067
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.543(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.058
_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)+(0.0828P)²+0.0928P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1347
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.457(4)
 0.543(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6431(3) 0.7231(10) 0.4277(2) 0.0518(9) Uani 1 1 d D . . . .
C1 C 0.7185(4) 0.6810(12) 0.4810(3) 0.0398(11) Uani 1 1 d . . . . .
C2 C 0.7021(3) 0.4849(12) 0.5436(3) 0.0364(10) Uani 1 1 d . . . . .
C3 C 0.6090(3) 0.3455(13) 0.5546(3) 0.0427(12) Uani 1 1 d . . . . .
H3 H 0.5584 0.3861 0.5196 0.051 Uiso 1 1 calc R . . . .
C4 C 0.5962(4) 0.1558(14) 0.6163(3) 0.0482(13) Uani 1 1 d . . . . .
H4 H 0.5360 0.0687 0.6228 0.058 Uiso 1 1 calc R . . . .
C5 C 0.6710(4) 0.0842(12) 0.6716(3) 0.0459(12) Uani 1 1 d . . . . .
C6 C 0.6587(5) -0.1111(16) 0.7358(3) 0.0639(16) Uani 1 1 d . . . . .
H6 H 0.5998 -0.2045 0.7431 0.077 Uiso 1 1 calc R . . . .
C7 C 0.7346(7) -0.1653(18) 0.7885(4) 0.074(2) Uani 1 1 d . . . . .
H7 H 0.7258 -0.2964 0.8305 0.089 Uiso 1 1 calc R . . . .
C8 C 0.8217(6) -0.0302(18) 0.7798(4) 0.073(2) Uani 1 1 d . . . . .
H8 H 0.8702 -0.0663 0.8171 0.087 Uiso 1 1 calc R . . . .
C9 C 0.8396(4) 0.1592(14) 0.7169(3) 0.0537(15) Uani 1 1 d . . . . .
C10 C 0.9297(4) 0.2991(16) 0.7040(4) 0.0610(17) Uani 1 1 d . . . . .
H10 H 0.9803 0.2599 0.7391 0.073 Uiso 1 1 calc R . . . .
C11 C 0.9446(4) 0.4864(17) 0.6429(4) 0.0587(16) Uani 1 1 d . . . . .
H11 H 1.0049 0.5734 0.6372 0.070 Uiso 1 1 calc R . . . .
C12 C 0.8701(3) 0.5548(13) 0.5869(3) 0.0434(11) Uani 1 1 d . . . . .
C13 C 0.8822(4) 0.7514(15) 0.5237(4) 0.0519(14) Uani 1 1 d . . . . .
H13 H 0.9415 0.8430 0.5169 0.062 Uiso 1 1 calc R . . . .
C14 C 0.8079(4) 0.8134(14) 0.4710(4) 0.0507(13) Uani 1 1 d . . . . .
H14 H 0.8178 0.9436 0.4289 0.061 Uiso 1 1 calc R . . . .
C15 C 0.7782(3) 0.4207(13) 0.5973(3) 0.0368(11) Uani 1 1 d . . . . .
C16 C 0.7622(3) 0.2246(14) 0.6621(3) 0.0411(11) Uani 1 1 d . . . . .
O2 O 0.3689(3) 0.7252(10) 0.6647(2) 0.0548(9) Uani 1 1 d D . . . .
C21 C 0.3000(4) 0.6744(12) 0.7224(3) 0.0413(11) Uani 1 1 d . . . . .
C22 C 0.3239(4) 0.4738(12) 0.7829(3) 0.0379(10) Uani 1 1 d . . . . .
C23 C 0.4181(4) 0.3461(13) 0.7903(3) 0.0447(12) Uani 1 1 d . . . . .
H23 H 0.4661 0.3949 0.7536 0.054 Uiso 1 1 calc R . . . .
C24 C 0.4378(4) 0.1554(13) 0.8503(3) 0.0513(14) Uani 1 1 d . . . . .
H24 H 0.4993 0.0754 0.8538 0.062 Uiso 1 1 calc R . . . .
C25 C 0.3677(4) 0.0739(13) 0.9078(3) 0.0464(12) Uani 1 1 d . . . . .
C26 C 0.3866(5) -0.1270(16) 0.9707(3) 0.0576(15) Uani 1 1 d . . . . .
H26 H 0.4474 -0.2116 0.9754 0.069 Uiso 1 1 calc R . . . .
C27 C 0.3152(5) -0.1969(15) 1.0248(4) 0.0633(17) Uani 1 1 d . . . . .
H27 H 0.3289 -0.3272 1.0662 0.076 Uiso 1 1 calc R . . . .
C28 C 0.2242(6) -0.0797(16) 1.0195(3) 0.0631(18) Uani 1 1 d . . . . .
H28 H 0.1774 -0.1333 1.0567 0.076 Uiso 1 1 calc R . . . .
C29 C 0.2010(4) 0.1185(14) 0.9589(3) 0.0515(14) Uani 1 1 d . . . . .
C30 C 0.1074(4) 0.2450(19) 0.9501(4) 0.0625(17) Uani 1 1 d . . . . .
H30 H 0.0589 0.1917 0.9858 0.075 Uiso 1 1 calc R . . . .
C31 C 0.0874(4) 0.4375(17) 0.8922(3) 0.0577(17) Uani 1 1 d . . . . .
H31 H 0.0258 0.5172 0.8893 0.069 Uiso 1 1 calc R . . . .
C32 C 0.1581(4) 0.5241(13) 0.8345(3) 0.0445(11) Uani 1 1 d . . . . .
C33 C 0.1391(4) 0.7265(15) 0.7744(3) 0.0514(12) Uani 1 1 d . . . . .
H33 H 0.0784 0.8130 0.7716 0.062 Uiso 1 1 calc R . . . .
C34 C 0.2097(4) 0.8026(13) 0.7179(3) 0.0486(13) Uani 1 1 d . . . . .
H34 H 0.1961 0.9379 0.6778 0.058 Uiso 1 1 calc R . . . .
C35 C 0.2521(3) 0.4004(12) 0.8404(3) 0.0372(10) Uani 1 1 d . . . . .
C36 C 0.2741(3) 0.1984(13) 0.9022(3) 0.0396(11) Uani 1 1 d . . . . .
H1 H 0.650(4) 0.886(8) 0.407(3) 0.056(18) Uiso 1 1 d D . . . .
H2 H 0.361(7) 0.874(12) 0.636(4) 0.12(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.385(6) . ?
C1 C2 1.393(8) . ?
C1 C14 1.389(8) . ?
C2 C3 1.450(7) . ?
C2 C15 1.414(6) . ?
C3 C4 1.356(8) . ?
C4 C5 1.425(8) . ?
C5 C6 1.403(8) . ?
C5 C16 1.426(8) . ?
C6 C7 1.392(10) . ?
C7 C8 1.363(12) . ?
C8 C9 1.381(10) . ?
C9 C10 1.420(9) . ?
C9 C16 1.439(7) . ?
C10 C11 1.345(9) . ?
C11 C12 1.426(7) . ?
C12 C13 1.393(8) . ?
C12 C15 1.424(7) . ?
C13 C14 1.381(8) . ?
C15 C16 1.420(8) . ?
O2 C21 1.374(6) . ?
C21 C22 1.401(8) . ?
C21 C34 1.383(7) . ?
C22 C23 1.435(7) . ?
C22 C35 1.421(7) . ?
C23 C24 1.354(8) . ?
C24 C25 1.413(7) . ?
C25 C26 1.418(8) . ?
C25 C36 1.420(8) . ?
C26 C27 1.376(9) . ?
C27 C28 1.373(10) . ?
C28 C29 1.393(9) . ?
C29 C30 1.427(10) . ?
C29 C36 1.432(7) . ?
C30 C31 1.335(10) . ?
C31 C32 1.427(8) . ?
C32 C33 1.389(8) . ?
C32 C35 1.423(7) . ?
C33 C34 1.401(8) . ?
C35 C36 1.416(8) . ?

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 C1 C2 116.4(4) . . ?
O1 C1 C14 122.4(5) . . ?
C14 C1 C2 121.1(5) . . ?
C1 C2 C3 121.6(4) . . ?
C1 C2 C15 119.0(4) . . ?
C15 C2 C3 119.5(5) . . ?
C4 C3 C2 119.6(5) . . ?
C3 C4 C5 122.8(5) . . ?
C4 C5 C16 118.0(5) . . ?
C6 C5 C4 123.4(6) . . ?
C6 C5 C16 118.6(5) . . ?
C7 C6 C5 120.1(7) . . ?
C8 C7 C6 121.4(7) . . ?
C7 C8 C9 121.6(6) . . ?
C8 C9 C10 123.7(6) . . ?
C8 C9 C16 118.5(6) . . ?
C10 C9 C16 117.8(5) . . ?
C11 C10 C9 122.4(5) . . ?
C10 C11 C12 121.6(6) . . ?
C13 C12 C11 123.3(5) . . ?
C13 C12 C15 118.5(5) . . ?
C15 C12 C11 118.2(5) . . ?
C14 C13 C12 121.5(5) . . ?
C13 C14 C1 119.9(6) . . ?
C2 C15 C12 120.1(4) . . ?
C2 C15 C16 119.7(4) . . ?
C16 C15 C12 120.3(4) . . ?
C5 C16 C9 119.7(5) . . ?
C15 C16 C5 120.5(4) . . ?
C15 C16 C9 119.8(5) . . ?
O2 C21 C22 116.6(5) . . ?
O2 C21 C34 121.2(5) . . ?
C34 C21 C22 122.1(5) . . ?
C21 C22 C23 123.0(5) . . ?
C21 C22 C35 118.2(5) . . ?
C35 C22 C23 118.8(5) . . ?
C24 C23 C22 120.6(5) . . ?
C23 C24 C25 122.1(5) . . ?
C24 C25 C26 123.0(6) . . ?
C24 C25 C36 118.5(5) . . ?
C26 C25 C36 118.5(5) . . ?
C27 C26 C25 120.1(6) . . ?
C28 C27 C26 121.8(6) . . ?
C27 C28 C29 120.8(6) . . ?
C28 C29 C30 123.2(6) . . ?
C28 C29 C36 118.7(6) . . ?
C30 C29 C36 118.1(6) . . ?
C31 C30 C29 122.0(5) . . ?
C30 C31 C32 121.7(6) . . ?
C33 C32 C31 122.6(5) . . ?
C33 C32 C35 119.2(5) . . ?
C35 C32 C31 118.2(5) . . ?
C32 C33 C34 121.1(5) . . ?
C21 C34 C33 119.3(5) . . ?
C22 C35 C32 120.0(5) . . ?
C36 C35 C22 119.6(4) . . ?
C36 C35 C32 120.4(5) . . ?
C25 C36 C29 120.0(5) . . ?
C35 C36 C25 120.4(5) . . ?
C35 C36 C29 119.6(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.457(4)
2 0.543(4)

####################################################################### 
# 
# 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_t300
_database_code_depnum_ccdc_archive 'CCDC 1892314'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 1-hydroxypyrene
;
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H10 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8662(7)
_cell_length_b                   4.58166(18)
_cell_length_c                   16.6568(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.015(4)
_cell_angle_gamma                90
_cell_volume                     1058.21(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3039
_cell_measurement_temperature    300.00(10)
_cell_measurement_theta_max      74.5320
_cell_measurement_theta_min      2.6530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6289
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         2.653
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1007565000
_diffrn_orient_matrix_UB_12      0.1408774000
_diffrn_orient_matrix_UB_13      -0.0033863000
_diffrn_orient_matrix_UB_21      0.0001848000
_diffrn_orient_matrix_UB_22      0.0287714000
_diffrn_orient_matrix_UB_23      0.0921545000
_diffrn_orient_matrix_UB_31      0.0466987000
_diffrn_orient_matrix_UB_32      -0.3041100000
_diffrn_orient_matrix_UB_33      0.0071086000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.524
_reflns_Friedel_fraction_full    0.681
_reflns_Friedel_fraction_max     0.687
_reflns_number_gt                2753
_reflns_number_total             3077
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.459(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.043
_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)+(0.1004P)²+0.0100P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1461
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.541(4)
 0.459(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
3.b Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6436(3) 0.7234(10) 0.4276(2) 0.0593(9) Uani 1 1 d . . . . .
H1 H 0.6440 0.8934 0.4122 0.089 Uiso 1 1 calc R . . . .
C1 C 0.7182(4) 0.6799(13) 0.4813(3) 0.0475(12) Uani 1 1 d . . . . .
C2 C 0.7024(3) 0.4854(12) 0.5434(3) 0.0436(10) Uani 1 1 d . . . . .
C3 C 0.6094(3) 0.3452(13) 0.5545(3) 0.0499(13) Uani 1 1 d . . . . .
H3 H 0.5590 0.3851 0.5193 0.060 Uiso 1 1 calc R . . . .
C4 C 0.5960(4) 0.1543(14) 0.6167(3) 0.0546(13) Uani 1 1 d . . . . .
H4 H 0.5360 0.0669 0.6231 0.066 Uiso 1 1 calc R . . . .
C5 C 0.6705(4) 0.0850(12) 0.6718(3) 0.0520(12) Uani 1 1 d . . . . .
C6 C 0.6583(6) -0.1105(16) 0.7357(4) 0.0718(17) Uani 1 1 d . . . . .
H6 H 0.5994 -0.2041 0.7427 0.086 Uiso 1 1 calc R . . . .
C7 C 0.7335(7) -0.1654(19) 0.7885(4) 0.083(2) Uani 1 1 d . . . . .
H7 H 0.7242 -0.2961 0.8305 0.099 Uiso 1 1 calc R . . . .
C8 C 0.8211(7) -0.0314(18) 0.7801(4) 0.083(2) Uani 1 1 d . . . . .
H8 H 0.8695 -0.0687 0.8175 0.100 Uiso 1 1 calc R . . . .
C9 C 0.8393(5) 0.1584(14) 0.7173(3) 0.0619(16) Uani 1 1 d . . . . .
C10 C 0.9294(5) 0.2997(16) 0.7040(4) 0.0681(17) Uani 1 1 d . . . . .
H10 H 0.9800 0.2621 0.7392 0.082 Uiso 1 1 calc R . . . .
C11 C 0.9445(4) 0.4847(17) 0.6428(4) 0.0659(16) Uani 1 1 d . . . . .
H11 H 1.0050 0.5698 0.6368 0.079 Uiso 1 1 calc R . . . .
C12 C 0.8697(4) 0.5545(13) 0.5865(3) 0.0502(12) Uani 1 1 d . . . . .
C13 C 0.8819(4) 0.7497(14) 0.5242(4) 0.0591(14) Uani 1 1 d . . . . .
H13 H 0.9411 0.8421 0.5176 0.071 Uiso 1 1 calc R . . . .
C14 C 0.8074(4) 0.8107(14) 0.4711(4) 0.0565(13) Uani 1 1 d . . . . .
H14 H 0.8173 0.9393 0.4287 0.068 Uiso 1 1 calc R . . . .
C15 C 0.7779(3) 0.4199(13) 0.5970(3) 0.0430(11) Uani 1 1 d . . . . .
C16 C 0.7622(4) 0.2242(14) 0.6622(3) 0.0475(11) Uani 1 1 d . . . . .
O2 O 0.3687(3) 0.7248(10) 0.6647(2) 0.0610(9) Uani 1 1 d . . . . .
H2 H 0.3491 0.8485 0.6331 0.092 Uiso 1 1 calc R . . . .
C21 C 0.2997(4) 0.6748(13) 0.7224(3) 0.0482(11) Uani 1 1 d . . . . .
C22 C 0.3239(4) 0.4733(11) 0.7830(3) 0.0440(11) Uani 1 1 d . . . . .
C23 C 0.4177(4) 0.3462(13) 0.7903(3) 0.0510(12) Uani 1 1 d . . . . .
H23 H 0.4655 0.3948 0.7535 0.061 Uiso 1 1 calc R . . . .
C24 C 0.4374(4) 0.1557(13) 0.8503(3) 0.0574(14) Uani 1 1 d . . . . .
H24 H 0.4989 0.0759 0.8536 0.069 Uiso 1 1 calc R . . . .
C25 C 0.3677(4) 0.0742(13) 0.9078(3) 0.0533(12) Uani 1 1 d . . . . .
C26 C 0.3869(5) -0.1263(16) 0.9708(4) 0.0660(16) Uani 1 1 d . . . . .
H26 H 0.4478 -0.2095 0.9757 0.079 Uiso 1 1 calc R . . . .
C27 C 0.3157(6) -0.1973(15) 1.0246(4) 0.0719(19) Uani 1 1 d . . . . .
H27 H 0.3291 -0.3297 1.0654 0.086 Uiso 1 1 calc R . . . .
C28 C 0.2248(6) -0.0771(16) 1.0195(3) 0.0674(17) Uani 1 1 d . . . . .
H28 H 0.1784 -0.1283 1.0573 0.081 Uiso 1 1 calc R . . . .
C29 C 0.2010(5) 0.1201(15) 0.9587(3) 0.0584(15) Uani 1 1 d . . . . .
C30 C 0.1078(4) 0.2465(19) 0.9505(4) 0.0678(17) Uani 1 1 d . . . . .
H30 H 0.0596 0.1944 0.9866 0.081 Uiso 1 1 calc R . . . .
C31 C 0.0878(4) 0.4380(18) 0.8925(3) 0.0661(17) Uani 1 1 d . . . . .
H31 H 0.0261 0.5169 0.8896 0.079 Uiso 1 1 calc R . . . .
C32 C 0.1586(4) 0.5258(13) 0.8345(3) 0.0510(12) Uani 1 1 d . . . . .
C33 C 0.1398(4) 0.7283(15) 0.7740(3) 0.0588(13) Uani 1 1 d . . . . .
H33 H 0.0793 0.8154 0.7711 0.071 Uiso 1 1 calc R . . . .
C34 C 0.2098(4) 0.8016(14) 0.7182(3) 0.0554(13) Uani 1 1 d . . . . .
H34 H 0.1961 0.9361 0.6779 0.067 Uiso 1 1 calc R . . . .
C35 C 0.2523(3) 0.4016(12) 0.8404(3) 0.0429(10) Uani 1 1 d . . . . .
C36 C 0.2742(4) 0.1988(13) 0.9021(3) 0.0462(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.383(6) . ?
C1 C2 1.383(8) . ?
C1 C14 1.385(8) . ?
C2 C3 1.452(7) . ?
C2 C15 1.408(6) . ?
C3 C4 1.369(8) . ?
C4 C5 1.418(8) . ?
C5 C6 1.400(8) . ?
C5 C16 1.432(8) . ?
C6 C7 1.388(11) . ?
C7 C8 1.368(13) . ?
C8 C9 1.384(11) . ?
C9 C10 1.425(9) . ?
C9 C16 1.441(7) . ?
C10 C11 1.342(10) . ?
C11 C12 1.435(8) . ?
C12 C13 1.380(9) . ?
C12 C15 1.425(7) . ?
C13 C14 1.388(8) . ?
C15 C16 1.425(8) . ?
O2 C21 1.376(6) . ?
C21 C22 1.409(8) . ?
C21 C34 1.378(8) . ?
C22 C23 1.430(7) . ?
C22 C35 1.416(7) . ?
C23 C24 1.355(8) . ?
C24 C25 1.411(8) . ?
C25 C26 1.420(9) . ?
C25 C36 1.420(8) . ?
C26 C27 1.372(10) . ?
C27 C28 1.378(11) . ?
C28 C29 1.397(9) . ?
C29 C30 1.422(10) . ?
C29 C36 1.433(7) . ?
C30 C31 1.335(11) . ?
C31 C32 1.436(8) . ?
C32 C33 1.395(9) . ?
C32 C35 1.421(7) . ?
C33 C34 1.386(8) . ?
C35 C36 1.419(8) . ?

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 C1 C2 117.3(5) . . ?
O1 C1 C14 121.7(5) . . ?
C2 C1 C14 120.9(5) . . ?
C1 C2 C3 121.4(5) . . ?
C1 C2 C15 119.5(4) . . ?
C15 C2 C3 119.1(5) . . ?
C4 C3 C2 119.9(5) . . ?
C3 C4 C5 122.3(5) . . ?
C4 C5 C16 118.3(5) . . ?
C6 C5 C4 123.1(6) . . ?
C6 C5 C16 118.5(6) . . ?
C7 C6 C5 120.4(7) . . ?
C8 C7 C6 121.4(7) . . ?
C7 C8 C9 121.4(7) . . ?
C8 C9 C10 124.3(6) . . ?
C8 C9 C16 118.6(7) . . ?
C10 C9 C16 117.2(5) . . ?
C11 C10 C9 122.8(5) . . ?
C10 C11 C12 121.6(6) . . ?
C13 C12 C11 123.2(5) . . ?
C13 C12 C15 118.8(5) . . ?
C15 C12 C11 118.0(5) . . ?
C12 C13 C14 121.2(5) . . ?
C1 C14 C13 120.0(6) . . ?
C2 C15 C12 119.6(5) . . ?
C2 C15 C16 120.2(5) . . ?
C16 C15 C12 120.2(4) . . ?
C5 C16 C9 119.6(5) . . ?
C15 C16 C5 120.1(4) . . ?
C15 C16 C9 120.2(5) . . ?
O2 C21 C22 116.4(5) . . ?
O2 C21 C34 121.6(5) . . ?
C34 C21 C22 121.8(5) . . ?
C21 C22 C23 122.9(5) . . ?
C21 C22 C35 118.0(5) . . ?
C35 C22 C23 119.1(5) . . ?
C24 C23 C22 120.5(5) . . ?
C23 C24 C25 122.2(5) . . ?
C24 C25 C26 123.0(6) . . ?
C24 C25 C36 118.3(5) . . ?
C36 C25 C26 118.7(5) . . ?
C27 C26 C25 120.1(6) . . ?
C26 C27 C28 121.6(6) . . ?
C27 C28 C29 121.3(6) . . ?
C28 C29 C30 123.2(6) . . ?
C28 C29 C36 118.2(7) . . ?
C30 C29 C36 118.6(6) . . ?
C31 C30 C29 121.8(5) . . ?
C30 C31 C32 121.9(6) . . ?
C33 C32 C31 123.0(5) . . ?
C33 C32 C35 119.1(5) . . ?
C35 C32 C31 117.9(5) . . ?
C34 C33 C32 121.0(5) . . ?
C21 C34 C33 119.9(5) . . ?
C22 C35 C32 120.1(5) . . ?
C22 C35 C36 119.3(5) . . ?
C36 C35 C32 120.5(5) . . ?
C25 C36 C29 120.1(5) . . ?
C35 C36 C25 120.5(5) . . ?
C35 C36 C29 119.3(5) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -3 1 0.2073 -0.0050 -2.9997 1.0145 -0.4265 0.0072 0.9192
0 3 -1 0.2742 0.0050 2.9997 -1.0145 0.4265 -0.0072 -0.9192
9 0 1 0.1093 9.0201 -0.0061 1.0046 0.9046 0.0941 0.4302
-9 0 -1 0.0682 -9.0201 0.0061 -1.0046 -0.9046 -0.0941 -0.4302
6 2 0 0.2423 6.0168 1.9957 -0.0066 0.8874 0.0579 -0.3260
1 0 -11 0.0295 1.0261 0.0011 -11.0040 0.1408 -1.0138 -0.0307
0 0 11 0.0248 -0.0236 -0.0018 11.0044 -0.0399 1.0141 0.0777
-1 0 11 0.0399 -1.0261 -0.0011 11.0040 -0.1408 1.0138 0.0307
-1 1 -10 0.0907 -0.9801 1.0021 -10.0092 0.0763 -0.8937 -0.4217
0 0 11 0.0331 -0.0236 -0.0018 11.0044 -0.0399 1.0141 0.0777

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.541(4)
2 0.459(4)

