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

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

data_hpd073a
_database_code_depnum_ccdc_archive 'CCDC 1988922'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_audit_creation_date             2020-01-29
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 F O2'
_chemical_formula_sum            'C16 H14 F O2'
_chemical_formula_weight         257.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N1O2F1
_chemical_oxdiff_usercomment     G451-5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.64360(10)
_cell_length_b                   36.3180(5)
_cell_length_c                   6.67680(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.690(2)
_cell_angle_gamma                90
_cell_volume                     1303.79(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8607
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.0710
_cell_measurement_theta_min      2.4210
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 18 0 0.0059
3 15 0 0.0243
1 -2 4 0.0789
-3 -15 0 0.0300
1 1 -4 0.0509
-2 9 4 0.0757
2 -18 0 0.0403

_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.048
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
-2.2858 18.0667 0.1904 -0.2206 -0.9197 0.3247
2.7114 15.0953 -0.1297 0.9723 -0.2337 -0.0089
0.5077 -2.4779 3.8839 0.2224 -0.0517 -0.9736
-2.7148 -15.4547 0.3808 -0.9709 0.2335 -0.0535
0.8114 0.9312 -4.3154 0.0650 0.2780 0.9584
-1.9441 9.0123 3.8231 -0.1766 -0.7396 -0.6495
2.2501 -18.0417 -0.0137 0.2185 0.9058 -0.3631

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15026
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.520
_diffrn_reflns_theta_min         2.433
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00   3.00   0.50    0.05    --  -46.87 105.00 168.00  168
  2  ω     18.00  85.00   0.50    0.05    --   46.87-105.00  68.00  134
  3  ω    -81.00 -15.00   0.50    0.21    --  -88.50 105.00 168.00  132
  4  ω   -160.00 -83.00   0.50    0.21    --  -88.50-105.00  68.00  154
  5  ω    105.00 178.00   0.50    0.21    --  106.69 105.00 168.00  146
  6  ω     34.00 106.00   0.50    0.21    --  106.69-105.00  68.00  144
  7  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00-150.00   66
  8  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00   0.00   74
  9  ω     83.00 120.00   0.50    0.05    --   46.87  57.00-180.00   74
 10  ω     83.00 120.00   0.50    0.05    --   46.87  57.00 150.00   74
 11  ω     83.00 120.00   0.50    0.05    --   46.87  57.00-120.00   74
 12  ω    -51.00 -16.00   0.50    0.21    --  -88.50  45.00 -30.00   70
 13  ω    -51.00 -16.00   0.50    0.21    --  -88.50  45.00 150.00   70
 14  ω    -51.00 -16.00   0.50    0.21    --  -88.50  45.00  30.00   70
 15  ω    -51.00 -16.00   0.50    0.21    --  -88.50  45.00 -60.00   70
 16  ω    -51.00 -16.00   0.50    0.21    --  -88.50  45.00   0.00   70
 17  ω    -51.00 -16.00   0.50    0.21    --  -88.50  45.00 120.00   70
 18  ω     34.00 101.00   0.50    0.21    --  106.69 -77.00  90.00  134
 19  ω     92.00 178.00   0.50    0.21    --  106.69  45.00 -30.00  172
 20  ω     34.00  71.00   0.50    0.21    --  106.69 -61.00 120.00   74
 21  ω     34.00  71.00   0.50    0.21    --  106.69 -61.00-150.00   74
 22  ω     95.00 178.00   0.50    0.21    --  106.69 125.00 -60.00  166
 23  ω     34.00  71.00   0.50    0.21    --  106.69 -61.00  90.00   74
 24  ω     34.00  71.00   0.50    0.21    --  106.69 -61.00-180.00   74
 25  ω     34.00  71.00   0.50    0.21    --  106.69 -61.00 -90.00   74
 26  ω     34.00  71.00   0.50    0.21    --  106.69 -61.00 -30.00   74
 27  ω     32.00 121.00   0.50    0.05    --   46.87  37.00 -30.00  178
 28  ω     32.00 121.00   0.50    0.05    --   46.87  37.00  90.00  178
 29  ω     83.00 120.00   0.50    0.05    --   46.87  57.00-150.00   74
 30  ω     32.00 121.00   0.50    0.05    --   46.87  37.00-180.00  178
 31  ω     83.00 120.00   0.50    0.05    --   46.87  57.00 120.00   74
 32  ω   -163.00-103.00   0.50    0.21    --  -88.50 -30.00  90.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2525481000
_diffrn_orient_matrix_UB_12      0.0193593000
_diffrn_orient_matrix_UB_13      0.0365939000
_diffrn_orient_matrix_UB_21      0.1125178000
_diffrn_orient_matrix_UB_22      -0.0361342000
_diffrn_orient_matrix_UB_23      -0.0510620000
_diffrn_orient_matrix_UB_31      -0.0752497000
_diffrn_orient_matrix_UB_32      0.0109162000
_diffrn_orient_matrix_UB_33      -0.2338760000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2515
_reflns_number_total             2642
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.046
_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)+(0.0200P)²+2.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1258
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C10A) = Uanis(C9A) = Uanis(C10B) = Uanis(C9B)
3. Others
 Fixed Sof: F1A(0.75) F1B(0.25) C10A(0.9) H10A(0.9) H10B(0.9) H10C(0.9)
 C9A(0.9) H9AA(0.9) H9AB(0.9) H7A(0.9) H7B(0.1) C9B(0.1) H9BA(0.1) H9BB(0.1)
 C10B(0.1) H10D(0.1) H10E(0.1) H10F(0.1)
4.a Riding coordinates:
 O1(H1)
4.b Ternary CH refined with riding coordinates:
 C7(H7A), C7(H7B)
4.c Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C9B(H9BA,H9BB)
4.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C16(H16), C6(H6), C14(H14), C2(H2), C13(H13)
4.e Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C10B(H10D,H10E,H10F)
;
_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
F1A F 1.2554(3) 0.12689(5) 0.3611(3) 0.0308(4) Uani 0.75 1 d . . P . .
O2 O 0.3515(3) 0.03709(4) -0.1234(3) 0.0355(4) Uani 1 1 d . . . . .
O1 O 0.7470(3) 0.02157(4) -0.0766(3) 0.0362(4) Uani 1 1 d . . . . .
H1 H 0.732031 0.009341 0.025725 0.054 Uiso 1 1 d R U . . .
F1B F 0.4734(9) 0.18110(13) 0.1606(7) 0.0261(10) Uani 0.25 1 d . . P . .
C4 C 0.8681(4) 0.15667(5) 0.2709(3) 0.0230(4) Uani 1 1 d . . . . .
C5 C 0.6255(4) 0.15792(6) 0.1348(3) 0.0271(5) Uani 1 1 d . . . . .
C12 C 1.1662(4) 0.20374(6) 0.4829(3) 0.0249(4) Uani 1 1 d . . . . .
H12 H 1.253756 0.203093 0.381900 0.030 Uiso 1 1 calc R U . . .
C11 C 0.9559(4) 0.18160(5) 0.4552(3) 0.0223(4) Uani 1 1 d . . . . .
C15 C 0.9151(4) 0.20567(6) 0.7809(3) 0.0265(5) Uani 1 1 d . . . . .
H15 H 0.829404 0.206175 0.883283 0.032 Uiso 1 1 calc R U . . .
C16 C 0.8309(4) 0.18301(6) 0.6061(3) 0.0242(4) Uani 1 1 d . . . . .
H16 H 0.686698 0.168336 0.588988 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5418(4) 0.13363(6) -0.0329(3) 0.0289(5) Uani 1 1 d . . . . .
H6 H 0.375786 0.135385 -0.123380 0.035 Uiso 1 1 calc R U . . .
C10A C 0.6620(6) 0.04884(7) -0.5695(4) 0.0361(5) Uani 0.9 1 d . . P A 1
H10A H 0.774825 0.047825 -0.655640 0.054 Uiso 0.9 1 calc R U P A 1
H10B H 0.499108 0.057934 -0.654849 0.054 Uiso 0.9 1 calc R U P A 1
H10C H 0.643522 0.024136 -0.517128 0.054 Uiso 0.9 1 calc R U P A 1
C14 C 1.1237(4) 0.22756(6) 0.8070(3) 0.0269(5) Uani 1 1 d . . . . .
H14 H 1.181035 0.243043 0.926649 0.032 Uiso 1 1 calc R U . . .
C1 C 0.6995(5) 0.10685(6) -0.0687(3) 0.0275(5) Uani 1 1 d . . . . .
C3 C 1.0230(4) 0.12997(6) 0.2277(3) 0.0267(5) Uani 1 1 d . . . . .
C8 C 0.5578(5) 0.04326(6) -0.1438(3) 0.0276(5) Uani 1 1 d . . . . .
C2 C 0.9441(5) 0.10522(6) 0.0635(4) 0.0304(5) Uani 1 1 d . . . . .
H2 H 1.055572 0.087242 0.040818 0.036 Uiso 1 1 calc R U . . .
C13 C 1.2482(4) 0.22666(6) 0.6567(3) 0.0279(5) Uani 1 1 d . . . . .
H13 H 1.390021 0.241797 0.672862 0.033 Uiso 1 1 calc R U . . .
C9A C 0.7684(6) 0.07470(7) -0.3843(4) 0.0361(5) Uani 0.9 1 d . . P A 1
H9AA H 0.931920 0.065156 -0.298013 0.043 Uiso 0.9 1 calc R U P A 1
H9AB H 0.796005 0.099190 -0.438410 0.043 Uiso 0.9 1 calc R U P A 1
C7 C 0.6013(5) 0.07904(6) -0.2461(3) 0.0331(5) Uani 1 1 d . . . . .
H7A H 0.436199 0.088084 -0.336782 0.040 Uiso 0.9 1 calc R U P A 1
H7B H 0.768681 0.071943 -0.255918 0.040 Uiso 0.1 1 calc R U P A 2
C9B C 0.510(5) 0.0840(7) -0.429(4) 0.0361(5) Uani 0.1 1 d . . P A 2
H9BA H 0.605301 0.104393 -0.466521 0.043 Uiso 0.1 1 calc R U P A 2
H9BB H 0.341268 0.093653 -0.446587 0.043 Uiso 0.1 1 calc R U P A 2
C10B C 0.481(6) 0.0541(7) -0.602(4) 0.0361(5) Uani 0.1 1 d . . P A 2
H10D H 0.318433 0.056793 -0.708854 0.054 Uiso 0.1 1 calc R U P A 2
H10E H 0.493144 0.029550 -0.538698 0.054 Uiso 0.1 1 calc R U P A 2
H10F H 0.612823 0.057050 -0.668537 0.054 Uiso 0.1 1 calc R U P A 2


_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
F1A C3 1.348(3) . ?
O2 C8 1.233(3) . ?
O1 H1 0.8401 . ?
O1 C8 1.293(3) . ?
F1B C5 1.251(5) . ?
C4 C5 1.395(3) . ?
C4 C11 1.486(3) . ?
C4 C3 1.393(3) . ?
C5 C6 1.391(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.399(3) . ?
C12 C13 1.388(3) . ?
C11 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C15 C14 1.387(3) . ?
C16 H16 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.387(3) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C10A C9A 1.523(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.389(3) . ?
C1 C2 1.396(3) . ?
C1 C7 1.527(3) . ?
C3 C2 1.383(3) . ?
C8 C7 1.522(3) . ?
C2 H2 0.9500 . ?
C13 H13 0.9500 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C7 1.515(3) . ?
C7 H7A 1.0000 . ?
C7 H7B 1.0000 . ?
C7 C9B 1.18(2) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.56(3) . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 H1 109.2 . . ?
C5 C4 C11 122.28(19) . . ?
C3 C4 C5 116.17(19) . . ?
C3 C4 C11 121.5(2) . . ?
F1B C5 C4 120.7(3) . . ?
F1B C5 C6 117.3(3) . . ?
C6 C5 C4 122.0(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C13 C12 C11 120.62(19) . . ?
C12 C11 C4 121.06(18) . . ?
C16 C11 C4 120.36(19) . . ?
C16 C11 C12 118.58(19) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.39(19) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C5 C6 H6 119.9 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.9 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C13 119.5(2) . . ?
C13 C14 H14 120.3 . . ?
C6 C1 C2 119.0(2) . . ?
C6 C1 C7 119.8(2) . . ?
C2 C1 C7 121.2(2) . . ?
F1A C3 C4 117.85(19) . . ?
F1A C3 C2 118.9(2) . . ?
C2 C3 C4 123.1(2) . . ?
O2 C8 O1 124.0(2) . . ?
O2 C8 C7 119.4(2) . . ?
O1 C8 C7 116.5(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C10A C9A H9AA 108.9 . . ?
C10A C9A H9AB 108.9 . . ?
H9AA C9A H9AB 107.8 . . ?
C7 C9A C10A 113.2(2) . . ?
C7 C9A H9AA 108.9 . . ?
C7 C9A H9AB 108.9 . . ?
C1 C7 H7A 107.7 . . ?
C1 C7 H7B 95.4 . . ?
C8 C7 C1 106.65(17) . . ?
C8 C7 H7A 107.7 . . ?
C8 C7 H7B 95.4 . . ?
C9A C7 C1 113.3(2) . . ?
C9A C7 C8 113.6(2) . . ?
C9A C7 H7A 107.7 . . ?
C9B C7 C1 129.8(12) . . ?
C9B C7 C8 120.9(12) . . ?
C9B C7 H7B 95.4 . . ?
C7 C9B H9BA 106.1 . . ?
C7 C9B H9BB 106.1 . . ?
C7 C9B C10B 125(2) . . ?
H9BA C9B H9BB 106.3 . . ?
C10B C9B H9BA 106.1 . . ?
C10B C9B H9BB 106.1 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1A C3 C2 C1 176.48(19) . . . . ?
O2 C8 C7 C1 91.8(3) . . . . ?
O2 C8 C7 C9A -142.7(2) . . . . ?
O2 C8 C7 C9B -71.4(16) . . . . ?
O1 C8 C7 C1 -85.9(2) . . . . ?
O1 C8 C7 C9A 39.6(3) . . . . ?
O1 C8 C7 C9B 110.9(16) . . . . ?
F1B C5 C6 C1 -179.0(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C11 C16 C15 178.63(19) . . . . ?
C4 C3 C2 C1 0.8(3) . . . . ?
C5 C4 C11 C12 -125.2(2) . . . . ?
C5 C4 C11 C16 55.6(3) . . . . ?
C5 C4 C3 F1A -177.20(19) . . . . ?
C5 C4 C3 C2 -1.5(3) . . . . ?
C5 C6 C1 C2 -1.3(3) . . . . ?
C5 C6 C1 C7 176.71(19) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
C11 C4 C5 F1B 2.0(4) . . . . ?
C11 C4 C5 C6 -177.59(19) . . . . ?
C11 C4 C3 F1A 1.2(3) . . . . ?
C11 C4 C3 C2 176.9(2) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C15 C14 C13 C12 -0.7(3) . . . . ?
C16 C15 C14 C13 0.0(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C6 C1 C7 C8 -102.4(2) . . . . ?
C6 C1 C7 C9A 131.9(2) . . . . ?
C6 C1 C7 C9B 58.7(18) . . . . ?
C10A C9A C7 C1 -176.2(2) . . . . ?
C10A C9A C7 C8 61.9(3) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C1 C7 C9B C10B 162.9(17) . . . . ?
C3 C4 C5 F1B -179.7(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C3 C4 C11 C12 56.5(3) . . . . ?
C3 C4 C11 C16 -122.7(2) . . . . ?
C8 C7 C9B C10B -38(3) . . . . ?
C2 C1 C7 C8 75.5(3) . . . . ?
C2 C1 C7 C9A -50.1(3) . . . . ?
C2 C1 C7 C9B -123.4(18) . . . . ?
C13 C12 C11 C4 -179.4(2) . . . . ?
C13 C12 C11 C16 -0.1(3) . . . . ?
C7 C1 C2 C3 -177.34(19) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.394
_oxdiff_exptl_absorpt_empirical_full_min 0.846
####################################################################### 
# 
# 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_hpd107
_database_code_depnum_ccdc_archive 'CCDC 1993289'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_audit_creation_date             2020-03-16
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H47 B N3 O2 P'
_chemical_formula_sum            'C28 H47 B N3 O2 P'
_chemical_formula_weight         499.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O4
_chemical_oxdiff_usercomment     'air sensitive sample'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.3547(2)
_cell_length_b                   17.4727(4)
_cell_length_c                   14.7370(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.889(2)
_cell_angle_gamma                90
_cell_volume                     2880.34(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11295
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3400
_cell_measurement_theta_min      3.9410
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.773
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1088
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 10 0.1243
7 1 0 0.0529
-7 -1 0 0.0249
1 -11 0 0.0188
3 1 -9 0.1126
-1 11 1 0.0191

_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.049
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
-1.8171 0.9754 9.5035 0.0319 0.1252 0.9916
7.1788 0.7860 0.4837 0.2309 0.9613 -0.1503
-7.2941 -0.6990 0.3250 -0.2269 -0.9455 0.2336
0.6235 -11.2848 -0.1254 0.9666 -0.2322 -0.1084
2.6093 1.4798 -9.3114 -0.2019 0.0504 -0.9781
-0.8826 11.1974 1.0392 -0.9518 0.2285 0.2049

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32219
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.534
_diffrn_reflns_theta_min         3.952
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00 120.00   0.50    0.40    --   46.62  55.00 -28.62  178
  2  ω     81.00 169.00   0.50    1.60    --  106.69 146.00-172.00  176
  3  ω     91.00 178.00   0.50    1.60    --  106.69  30.00 120.00  174
  4  ω     46.00 127.00   0.50    1.60    --  106.69-146.00 136.00  162
  5  ω     46.00 108.00   0.50    0.40    --   46.62-146.00 136.00  124
  6  ω     34.00 101.00   0.50    1.60    --  106.69 -77.00  90.00  134
  7  ω     34.00  71.00   0.50    1.60    --  106.69 -61.00  90.00   74
  8  ω     34.00  71.00   0.50    1.60    --  106.69 -61.00 120.00   74
  9  ω     34.00  95.00   0.50    0.40    --   46.62-124.00 -57.00  122
 10  ω     34.00 111.00   0.50    1.60    --  106.69-124.00 -57.00  154
 11  ω     34.00  71.00   0.50    1.60    --  106.69 -61.00 -60.00   74
 12  ω     34.00 101.00   0.50    1.60    --  106.69 -77.00 -60.00  134
 13  ω     34.00 105.00   0.50    1.60    --  106.69 -94.00 -60.00  142
 14  ω     34.00  71.00   0.50    1.60    --  106.69 -61.00-180.00   74
 15  ω    -85.00 -12.00   0.50    0.40    --  -46.62 124.00  21.00  146
 16  ω    -51.00 -16.00   0.50    1.60    --  -88.50  45.00-180.00   70
 17  ω    -51.00 -16.00   0.50    1.60    --  -88.50  45.00-150.00   70
 18  ω    -51.00 -16.00   0.50    1.60    --  -88.50  45.00-120.00   70
 19  ω    -51.00 -16.00   0.50    1.60    --  -88.50  45.00 -60.00   70
 20  ω   -102.00 -24.00   0.50    1.60    --  -88.50 146.00-172.00  156
 21  ω   -119.00 -83.00   0.50    0.40    --  -46.62 -57.00 120.00   72
 22  ω   -119.00 -83.00   0.50    0.40    --  -46.62 -57.00 150.00   72
 23  ω   -119.00 -87.00   0.50    0.40    --  -46.62-125.00  60.00   64
 24  ω   -119.00 -59.00   0.50    0.40    --  -46.62-146.00 136.00  120
 25  ω   -160.00 -74.00   0.50    1.60    --  -88.50-124.00 -57.00  172
 26  ω   -119.00 -83.00   0.50    0.40    --  -46.62 -57.00-150.00   72
 27  ω   -119.00 -83.00   0.50    0.40    --  -46.62 -57.00-180.00   72
 28  ω   -119.00 -83.00   0.50    0.40    --  -46.62 -57.00 -90.00   72
 29  ω   -160.00-101.00   0.50    1.60    --  -88.50 -77.00  60.00  118
 30  ω    -51.00 -16.00   0.50    1.60    --  -88.50  45.00 150.00   70
 31  ω    -71.00 -15.00   0.50    1.60    --  -88.50  61.00 120.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0399995000
_diffrn_orient_matrix_UB_12      -0.0836636000
_diffrn_orient_matrix_UB_13      0.0195920000
_diffrn_orient_matrix_UB_21      0.1285665000
_diffrn_orient_matrix_UB_22      0.0272925000
_diffrn_orient_matrix_UB_23      0.0349577000
_diffrn_orient_matrix_UB_31      -0.0283113000
_diffrn_orient_matrix_UB_32      0.0069478000
_diffrn_orient_matrix_UB_33      0.0982160000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5058
_reflns_number_total             5795
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1165
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C23(H23A,H23B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6), C4(H4), C11(H11), C15(H15), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C8(H8A,H8B,H8C), C22(H22A,H22B,H22C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C26(H26A,
 H26B,H26C), C24(H24A,H24B,H24C), C20(H20A,H20B,H20C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.31607(4) 0.56586(2) 0.70400(3) 0.02558(12) Uani 1 1 d . . . . .
O1 O 0.37083(10) 0.58026(7) 0.61371(7) 0.0265(2) Uani 1 1 d . . . . .
O2 O 0.61372(10) 0.71680(7) 0.62778(8) 0.0284(3) Uani 1 1 d . . . . .
N1 N 0.28023(13) 0.64268(8) 0.75397(9) 0.0297(3) Uani 1 1 d . . . . .
N3 N 0.41021(13) 0.51936(8) 0.77819(9) 0.0293(3) Uani 1 1 d . . . . .
N2 N 0.20212(13) 0.51246(9) 0.66616(10) 0.0311(3) Uani 1 1 d . . . . .
C2 C 0.35382(15) 0.71601(10) 0.56930(10) 0.0275(3) Uani 1 1 d . . . . .
C10 C 0.62342(15) 0.58163(10) 0.66192(11) 0.0286(3) Uani 1 1 d . . . . .
C3 C 0.39148(15) 0.79283(10) 0.57880(11) 0.0288(3) Uani 1 1 d . . . . .
H3 H 0.470771 0.804292 0.607957 0.035 Uiso 1 1 calc R U . . .
C5 C 0.19755(15) 0.83859(10) 0.50170(11) 0.0287(3) Uani 1 1 d . . . . .
C9 C 0.55353(15) 0.65240(10) 0.62829(11) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.43280(15) 0.65227(10) 0.60462(11) 0.0276(3) Uani 1 1 d . . . . .
C7 C 0.23529(15) 0.70314(10) 0.52598(11) 0.0295(4) Uani 1 1 d . . . . .
H7 H 0.206168 0.652126 0.519262 0.035 Uiso 1 1 calc R U . . .
C6 C 0.15953(16) 0.76302(10) 0.49271(11) 0.0309(4) Uani 1 1 d . . . . .
H6 H 0.080191 0.752045 0.463237 0.037 Uiso 1 1 calc R U . . .
C4 C 0.31428(15) 0.85192(10) 0.54613(11) 0.0289(3) Uani 1 1 d . . . . .
H4 H 0.341865 0.903207 0.554293 0.035 Uiso 1 1 calc R U . . .
C11 C 0.68841(15) 0.58024(10) 0.75132(11) 0.0303(4) Uani 1 1 d . . . . .
H11 H 0.682137 0.621940 0.791574 0.036 Uiso 1 1 calc R U . . .
C15 C 0.63228(16) 0.51916(10) 0.60519(12) 0.0322(4) Uani 1 1 d . . . . .
H15 H 0.588352 0.518730 0.544212 0.039 Uiso 1 1 calc R U . . .
C13 C 0.77179(16) 0.45607(11) 0.72529(13) 0.0341(4) Uani 1 1 d . . . . .
C12 C 0.76180(16) 0.51910(11) 0.78225(12) 0.0335(4) Uani 1 1 d . . . . .
H12 H 0.806144 0.519858 0.843094 0.040 Uiso 1 1 calc R U . . .
C25 C 0.72934(16) 0.82440(10) 0.57684(12) 0.0336(4) Uani 1 1 d . . . . .
H25A H 0.652860 0.840583 0.538881 0.040 Uiso 1 1 calc R U . . .
H25B H 0.732034 0.845797 0.639366 0.040 Uiso 1 1 calc R U . . .
C17 C 0.36966(17) 0.69756(11) 0.79916(12) 0.0348(4) Uani 1 1 d . . . . .
H17A H 0.449506 0.674776 0.805394 0.052 Uiso 1 1 calc R U . . .
H17B H 0.352451 0.710294 0.860316 0.052 Uiso 1 1 calc R U . . .
H17C H 0.366615 0.744199 0.761886 0.052 Uiso 1 1 calc R U . . .
C14 C 0.70479(16) 0.45723(11) 0.63678(13) 0.0354(4) Uani 1 1 d . . . . .
H14 H 0.708720 0.414794 0.597114 0.042 Uiso 1 1 calc R U . . .
C8 C 0.11593(16) 0.90406(11) 0.46606(12) 0.0349(4) Uani 1 1 d . . . . .
H8A H 0.044379 0.884021 0.426459 0.052 Uiso 1 1 calc R U . . .
H8B H 0.157844 0.939034 0.430497 0.052 Uiso 1 1 calc R U . . .
H8C H 0.092552 0.931642 0.518083 0.052 Uiso 1 1 calc R U . . .
C22 C 0.43064(17) 0.52938(12) 0.87856(11) 0.0366(4) Uani 1 1 d . . . . .
H22A H 0.382014 0.572073 0.894435 0.055 Uiso 1 1 calc R U . . .
H22B H 0.515370 0.540357 0.900581 0.055 Uiso 1 1 calc R U . . .
H22C H 0.408188 0.482407 0.907679 0.055 Uiso 1 1 calc R U . . .
C19 C 0.13638(17) 0.50889(11) 0.57207(12) 0.0375(4) Uani 1 1 d . . . . .
H19A H 0.066489 0.542596 0.566154 0.056 Uiso 1 1 calc R U . . .
H19B H 0.110079 0.456194 0.557654 0.056 Uiso 1 1 calc R U . . .
H19C H 0.188407 0.525495 0.529207 0.056 Uiso 1 1 calc R U . . .
C23 C 0.71652(17) 0.69003(11) 0.48342(12) 0.0348(4) Uani 1 1 d . . . . .
H23A H 0.791363 0.697661 0.458631 0.042 Uiso 1 1 calc R U . . .
H23B H 0.706737 0.634320 0.491889 0.042 Uiso 1 1 calc R U . . .
C27 C 0.84955(16) 0.70000(12) 0.65191(13) 0.0367(4) Uani 1 1 d . . . . .
H27A H 0.842847 0.643758 0.657401 0.044 Uiso 1 1 calc R U . . .
H27B H 0.920253 0.710624 0.622872 0.044 Uiso 1 1 calc R U . . .
C21 C 0.45651(17) 0.44659(10) 0.74828(12) 0.0339(4) Uani 1 1 d . . . . .
H21A H 0.417051 0.403790 0.773883 0.051 Uiso 1 1 calc R U . . .
H21B H 0.542923 0.443793 0.770174 0.051 Uiso 1 1 calc R U . . .
H21C H 0.440397 0.443733 0.680870 0.051 Uiso 1 1 calc R U . . .
C18 C 0.15803(16) 0.67305(11) 0.73613(12) 0.0354(4) Uani 1 1 d . . . . .
H18A H 0.153096 0.714842 0.691277 0.053 Uiso 1 1 calc R U . . .
H18B H 0.136966 0.692350 0.793696 0.053 Uiso 1 1 calc R U . . .
H18C H 0.102373 0.632264 0.711479 0.053 Uiso 1 1 calc R U . . .
C16 C 0.84867(19) 0.38847(12) 0.75938(15) 0.0438(5) Uani 1 1 d . . . . .
H16A H 0.921276 0.406244 0.799663 0.066 Uiso 1 1 calc R U . . .
H16B H 0.870564 0.360920 0.706795 0.066 Uiso 1 1 calc R U . . .
H16C H 0.804285 0.354171 0.793928 0.066 Uiso 1 1 calc R U . . .
C26 C 0.83233(19) 0.85867(12) 0.53548(15) 0.0425(5) Uani 1 1 d . . . . .
H26A H 0.829305 0.839098 0.472807 0.064 Uiso 1 1 calc R U . . .
H26B H 0.908629 0.844302 0.573465 0.064 Uiso 1 1 calc R U . . .
H26C H 0.824992 0.914557 0.533696 0.064 Uiso 1 1 calc R U . . .
C24 C 0.61196(18) 0.71862(12) 0.41218(13) 0.0411(4) Uani 1 1 d . . . . .
H24A H 0.615294 0.694845 0.352444 0.062 Uiso 1 1 calc R U . . .
H24B H 0.617016 0.774362 0.406545 0.062 Uiso 1 1 calc R U . . .
H24C H 0.536477 0.705002 0.431839 0.062 Uiso 1 1 calc R U . . .
C20 C 0.14145(18) 0.47272(12) 0.73336(14) 0.0421(5) Uani 1 1 d . . . . .
H20A H 0.191807 0.474755 0.794388 0.063 Uiso 1 1 calc R U . . .
H20B H 0.127396 0.419206 0.714699 0.063 Uiso 1 1 calc R U . . .
H20C H 0.064817 0.497784 0.735684 0.063 Uiso 1 1 calc R U . . .
C28 C 0.87115(18) 0.73456(13) 0.74885(13) 0.0435(5) Uani 1 1 d . . . . .
H28A H 0.906244 0.785658 0.746952 0.065 Uiso 1 1 calc R U . . .
H28B H 0.926028 0.701707 0.790308 0.065 Uiso 1 1 calc R U . . .
H28C H 0.794995 0.738447 0.771329 0.065 Uiso 1 1 calc R U . . .
B1 B 0.73079(17) 0.73142(12) 0.58387(13) 0.0303(4) 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
P1 O1 1.5826(11) . ?
P1 N1 1.6163(15) . ?
P1 N3 1.6114(14) . ?
P1 N2 1.6149(15) . ?
O1 C1 1.459(2) . ?
O2 C9 1.317(2) . ?
O2 B1 1.596(2) . ?
N1 C17 1.470(2) . ?
N1 C18 1.467(2) . ?
N3 C22 1.468(2) . ?
N3 C21 1.472(2) . ?
N2 C19 1.459(2) . ?
N2 C20 1.474(2) . ?
C2 C3 1.408(2) . ?
C2 C1 1.468(2) . ?
C2 C7 1.405(2) . ?
C10 C9 1.506(2) . ?
C10 C11 1.395(2) . ?
C10 C15 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C5 C6 1.388(2) . ?
C5 C4 1.393(2) . ?
C5 C8 1.509(2) . ?
C9 C1 1.355(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.389(2) . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.391(3) . ?
C13 C12 1.401(3) . ?
C13 C14 1.393(3) . ?
C13 C16 1.503(3) . ?
C12 H12 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.530(3) . ?
C25 B1 1.628(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C14 H14 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.528(3) . ?
C23 B1 1.630(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.532(3) . ?
C27 B1 1.631(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N1 114.65(7) . . ?
O1 P1 N3 109.87(7) . . ?
O1 P1 N2 102.04(7) . . ?
N3 P1 N1 107.41(7) . . ?
N3 P1 N2 109.98(8) . . ?
N2 P1 N1 112.81(8) . . ?
C1 O1 P1 118.66(10) . . ?
C9 O2 B1 127.46(13) . . ?
C17 N1 P1 122.66(12) . . ?
C18 N1 P1 121.56(12) . . ?
C18 N1 C17 113.81(14) . . ?
C22 N3 P1 126.52(12) . . ?
C22 N3 C21 113.70(14) . . ?
C21 N3 P1 117.50(11) . . ?
C19 N2 P1 127.00(12) . . ?
C19 N2 C20 113.37(14) . . ?
C20 N2 P1 118.64(12) . . ?
C3 C2 C1 122.09(15) . . ?
C7 C2 C3 116.64(15) . . ?
C7 C2 C1 121.26(15) . . ?
C11 C10 C9 119.23(15) . . ?
C15 C10 C9 122.38(15) . . ?
C15 C10 C11 118.25(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.82(16) . . ?
C4 C3 H3 119.6 . . ?
C6 C5 C4 117.32(16) . . ?
C6 C5 C8 121.70(16) . . ?
C4 C5 C8 120.97(16) . . ?
O2 C9 C10 117.29(14) . . ?
O2 C9 C1 120.19(15) . . ?
C1 C9 C10 122.39(15) . . ?
O1 C1 C2 114.32(14) . . ?
C9 C1 O1 117.41(15) . . ?
C9 C1 C2 128.26(16) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.78(16) . . ?
C6 C7 H7 119.1 . . ?
C5 C6 C7 121.26(16) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C3 C4 C5 122.17(16) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.05(16) . . ?
C12 C11 H11 119.5 . . ?
C10 C15 H15 119.7 . . ?
C10 C15 C14 120.66(16) . . ?
C14 C15 H15 119.7 . . ?
C12 C13 C16 121.30(17) . . ?
C14 C13 C12 117.53(16) . . ?
C14 C13 C16 121.13(18) . . ?
C11 C12 C13 121.05(16) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
H25A C25 H25B 107.6 . . ?
C26 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C26 C25 B1 114.57(16) . . ?
B1 C25 H25A 108.6 . . ?
B1 C25 H25B 108.6 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C14 C13 121.44(17) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H23A C23 H23B 107.5 . . ?
C24 C23 H23A 108.5 . . ?
C24 C23 H23B 108.5 . . ?
C24 C23 B1 115.04(15) . . ?
B1 C23 H23A 108.5 . . ?
B1 C23 H23B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
C28 C27 H27A 108.5 . . ?
C28 C27 H27B 108.5 . . ?
C28 C27 B1 115.07(16) . . ?
B1 C27 H27A 108.5 . . ?
B1 C27 H27B 108.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O2 B1 C25 100.69(13) . . ?
O2 B1 C23 109.72(14) . . ?
O2 B1 C27 110.80(14) . . ?
C25 B1 C23 112.74(15) . . ?
C25 B1 C27 111.92(15) . . ?
C23 B1 C27 110.58(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C1 C2 -84.03(14) . . . . ?
P1 O1 C1 C9 96.57(15) . . . . ?
O1 P1 N1 C17 -67.85(14) . . . . ?
O1 P1 N1 C18 95.16(14) . . . . ?
O1 P1 N3 C22 143.69(15) . . . . ?
O1 P1 N3 C21 -54.57(14) . . . . ?
O1 P1 N2 C19 -25.14(17) . . . . ?
O1 P1 N2 C20 167.03(14) . . . . ?
O2 C9 C1 O1 -175.19(13) . . . . ?
O2 C9 C1 C2 5.5(3) . . . . ?
N1 P1 O1 C1 26.90(13) . . . . ?
N1 P1 N3 C22 18.37(17) . . . . ?
N1 P1 N3 C21 -179.89(13) . . . . ?
N1 P1 N2 C19 98.39(16) . . . . ?
N1 P1 N2 C20 -69.44(16) . . . . ?
N3 P1 O1 C1 -94.16(12) . . . . ?
N3 P1 N1 C17 54.55(15) . . . . ?
N3 P1 N1 C18 -142.43(13) . . . . ?
N3 P1 N2 C19 -141.72(15) . . . . ?
N3 P1 N2 C20 50.45(16) . . . . ?
N2 P1 O1 C1 149.18(11) . . . . ?
N2 P1 N1 C17 175.91(13) . . . . ?
N2 P1 N1 C18 -21.07(16) . . . . ?
N2 P1 N3 C22 -104.75(16) . . . . ?
N2 P1 N3 C21 56.99(15) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C2 C7 C6 C5 -0.6(2) . . . . ?
C10 C9 C1 O1 0.6(2) . . . . ?
C10 C9 C1 C2 -178.67(15) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C10 C15 C14 C13 -0.8(3) . . . . ?
C3 C2 C1 O1 162.67(14) . . . . ?
C3 C2 C1 C9 -18.0(3) . . . . ?
C3 C2 C7 C6 1.1(2) . . . . ?
C9 O2 B1 C25 161.68(14) . . . . ?
C9 O2 B1 C23 42.6(2) . . . . ?
C9 O2 B1 C27 -79.8(2) . . . . ?
C9 C10 C11 C12 -174.43(16) . . . . ?
C9 C10 C15 C14 175.20(16) . . . . ?
C1 C2 C3 C4 -178.91(15) . . . . ?
C1 C2 C7 C6 179.67(15) . . . . ?
C7 C2 C3 C4 -0.3(2) . . . . ?
C7 C2 C1 O1 -15.8(2) . . . . ?
C7 C2 C1 C9 163.48(16) . . . . ?
C6 C5 C4 C3 1.3(2) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C11 C10 C9 O2 59.4(2) . . . . ?
C11 C10 C9 C1 -116.51(19) . . . . ?
C11 C10 C15 C14 -0.5(3) . . . . ?
C15 C10 C9 O2 -116.18(18) . . . . ?
C15 C10 C9 C1 67.9(2) . . . . ?
C15 C10 C11 C12 1.4(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C14 C13 C12 C11 -0.3(3) . . . . ?
C8 C5 C6 C7 -179.82(15) . . . . ?
C8 C5 C4 C3 -179.41(15) . . . . ?
C16 C13 C12 C11 -178.23(17) . . . . ?
C16 C13 C14 C15 179.15(17) . . . . ?
C26 C25 B1 O2 -179.50(14) . . . . ?
C26 C25 B1 C23 -62.7(2) . . . . ?
C26 C25 B1 C27 62.8(2) . . . . ?
C24 C23 B1 O2 60.9(2) . . . . ?
C24 C23 B1 C25 -50.5(2) . . . . ?
C24 C23 B1 C27 -176.60(15) . . . . ?
C28 C27 B1 O2 -57.5(2) . . . . ?
C28 C27 B1 C25 54.0(2) . . . . ?
C28 C27 B1 C23 -179.41(16) . . . . ?
B1 O2 C9 C10 51.2(2) . . . . ?
B1 O2 C9 C1 -132.81(16) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.792
####################################################################### 
# 
# 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_hpd094b
_database_code_depnum_ccdc_archive 'CCDC 1988924'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-03-08 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_audit_creation_date             2020-02-21
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8.5 H8.5 N0.5 O)'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N1O2
_chemical_oxdiff_usercomment     G472-14
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   23.0271(3)
_cell_length_b                   5.71750(10)
_cell_length_c                   20.8790(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2748.88(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10373
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2450
_cell_measurement_theta_min      4.3730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
15 0 0 0.0494
-4 -3 -2 0.0657
-15 -1 -1 0.0476
1 4 2 0.0436
8 -1 -11 0.0093
1 -1 13 0.0397
-6 0 12 0.0393
-2 1 -13 0.0077

_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.048
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
14.8276 -0.4596 0.1970 0.0394 -0.4826 0.8749
-4.1845 -3.4995 -2.4142 -0.0731 0.9400 0.3333
-14.7586 -0.5273 -0.8361 -0.0560 0.6985 -0.7134
1.3777 3.6356 2.4089 0.0665 -0.8595 -0.5068
7.7788 -0.7827 -11.2133 -0.7921 -0.0632 0.6071
1.0964 -0.9378 13.0824 0.9882 0.0772 0.1326
-5.7582 0.3456 12.4432 0.8971 0.0711 -0.4361
-2.3354 1.1432 -12.7273 -0.9693 -0.0755 -0.2339

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25602
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.662
_diffrn_reflns_theta_min         3.839
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 120.00   0.50    1.00    --   46.62  73.00 -33.00  190
  2  ω     85.00 178.00   0.50    4.00    --  106.69  73.00 -33.00  186
  3  ω     45.00  71.00   0.50    4.00    --  106.69 -61.00 120.00   52
  4  ω     34.00 101.00   0.50    4.00    --  106.69 -77.00  30.00  134
  5  ω     34.00 101.00   0.50    4.00    --  106.69 -77.00 -90.00  134
  6  ω     34.00  91.00   0.50    4.00    --  106.69 -73.00-162.00  114
  7  ω     34.00  71.00   0.50    4.00    --  106.69 -61.00-120.00   74
  8  ω     41.00  71.00   0.50    4.00    --  106.69 -61.00-150.00   60
  9  ω     34.00 111.00   0.50    4.00    --  106.69-125.00-180.00  154
 10  ω     34.00  71.00   0.50    4.00    --  106.69 -61.00 -30.00   74
 11  ω    -25.00  69.00   0.50    1.00    --   46.62 -73.00-162.00  188
 12  ω    -69.00  26.00   0.50    1.00    --  -46.62  73.00 -33.00  190
 13  ω    -51.00 -16.00   0.50    4.00    --  -88.50  45.00 150.00   70
 14  ω    -91.00 -15.00   0.50    4.00    --  -88.50  73.00 -33.00  152
 15  ω    -51.00 -16.00   0.50    4.00    --  -88.50  45.00-120.00   70
 16  ω   -119.00 -24.00   0.50    1.00    --  -46.62 -73.00-162.00  190
 17  ω   -119.00 -87.00   0.50    1.00    --  -46.62-125.00   0.00   64
 18  ω   -119.00 -87.00   0.50    1.00    --  -46.62-125.00 120.00   64
 19  ω   -160.00-101.00   0.50    4.00    --  -88.50 -77.00  90.00  118
 20  ω   -160.00-100.00   0.50    4.00    --  -88.50 -94.00 -30.00  120
 21  ω   -160.00 -66.00   0.50    4.00    --  -88.50 -73.00-162.00  188
 22  ω   -160.00 -91.00   0.50    4.00    --  -88.50 -61.00 -90.00  138
 23  ω   -160.00 -91.00   0.50    4.00    --  -88.50 -61.00 -60.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0007342000
_diffrn_orient_matrix_UB_12      -0.0305535000
_diffrn_orient_matrix_UB_13      0.0732821000
_diffrn_orient_matrix_UB_21      -0.0392017000
_diffrn_orient_matrix_UB_22      -0.2173221000
_diffrn_orient_matrix_UB_23      -0.0063922000
_diffrn_orient_matrix_UB_31      0.0542387000
_diffrn_orient_matrix_UB_32      -0.1562328000
_diffrn_orient_matrix_UB_33      -0.0056102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                5006
_reflns_number_total             5316
_reflns_odcompleteness_completeness 99.97
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5316
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.079
_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)+(0.0300P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1298
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7(5)
 0.3(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 H1-O3
 1.9 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C13(H13), C30(H30)
4.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C32(H32A,H32B)
4.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C26(H26), C29(H29), C6(H6), C24(H24), C7(H7), C3(H3), C20(H20),
 C9(H9), C19(H19), C12(H12), C8(H8), C2(H2), C25(H25)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C34(H34A,H34B,H34C), C17(H17A,H17B,H17C), C33(H33A,H33B,
 H33C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57842(14) 0.3580(6) 0.56627(16) 0.0323(7) Uani 1 1 d . . . . .
H1 H 0.590534 0.341446 0.529621 0.048 Uiso 1 1 calc DR U . . .
O2 O 0.59969(14) 0.7320(6) 0.54783(17) 0.0346(8) Uani 1 1 d . . . . .
O4 O 0.65246(14) 0.6658(6) 0.43481(16) 0.0312(8) Uani 1 1 d . . . . .
H4 H 0.638652 0.683855 0.470676 0.047 Uiso 1 1 calc R U . . .
O3 O 0.63044(14) 0.2900(6) 0.45309(17) 0.0366(8) Uani 1 1 d D . . . .
N1 N 0.30381(15) 0.7071(6) 0.57393(18) 0.0246(8) Uani 1 1 d . . . . .
N2 N 0.92645(15) 0.2780(6) 0.42580(19) 0.0247(8) Uani 1 1 d . . . . .
C4 C 0.36296(18) 0.7162(8) 0.5846(2) 0.0240(9) Uani 1 1 d . . . . .
C14 C 0.57701(17) 0.5790(9) 0.5804(2) 0.0265(10) Uani 1 1 d . . . . .
C5 C 0.28115(19) 0.5165(8) 0.6064(2) 0.0243(9) Uani 1 1 d . . . . .
C27 C 0.90562(18) 0.5872(7) 0.3608(2) 0.0232(9) Uani 1 1 d . . . . .
C28 C 0.85167(18) 0.4670(8) 0.3753(2) 0.0235(9) Uani 1 1 d . . . . .
C23 C 1.00794(19) 0.5382(9) 0.3895(2) 0.0278(10) Uani 1 1 d . . . . .
H23 H 1.037055 0.462151 0.412258 0.033 Uiso 1 1 calc R U . . .
C21 C 0.86705(19) 0.2766(8) 0.4151(2) 0.0261(10) Uani 1 1 d . . . . .
C26 C 0.9191(2) 0.7793(8) 0.3229(2) 0.0302(10) Uani 1 1 d . . . . .
H26 H 0.889897 0.859701 0.301397 0.036 Uiso 1 1 calc R U . . .
C29 C 0.79381(18) 0.5037(8) 0.3578(2) 0.0262(9) Uani 1 1 d . . . . .
H29 H 0.783609 0.629306 0.331853 0.031 Uiso 1 1 calc R U . . .
C10 C 0.32673(19) 0.3994(8) 0.6390(2) 0.0258(9) Uani 1 1 d . . . . .
C11 C 0.37901(18) 0.5265(8) 0.6241(2) 0.0255(9) Uani 1 1 d . . . . .
C31 C 0.65387(18) 0.4445(9) 0.4211(2) 0.0287(10) Uani 1 1 d . . . . .
C22 C 0.94998(18) 0.4659(8) 0.3932(2) 0.0234(9) Uani 1 1 d . . . . .
C16 C 0.6230(2) 0.7952(9) 0.7091(2) 0.0310(11) Uani 1 1 d . . . . .
H16A H 0.649902 0.735927 0.677958 0.046 Uiso 1 1 calc R U . . .
H16B H 0.617960 0.681866 0.742591 0.046 Uiso 1 1 calc R U . . .
H16C H 0.637914 0.937776 0.727025 0.046 Uiso 1 1 calc R U . . .
C18 C 0.75184(19) 0.3493(9) 0.3800(2) 0.0276(10) Uani 1 1 d . . . . .
C6 C 0.22390(19) 0.4379(8) 0.6103(2) 0.0277(10) Uani 1 1 d . . . . .
H6 H 0.194266 0.512037 0.587893 0.033 Uiso 1 1 calc R U . . .
C24 C 1.02014(19) 0.7280(8) 0.3504(3) 0.0304(10) Uani 1 1 d . . . . .
H24 H 1.058473 0.776317 0.345677 0.036 Uiso 1 1 calc R U . . .
C7 C 0.2128(2) 0.2475(8) 0.6485(2) 0.0308(10) Uani 1 1 d . . . . .
H7 H 0.174807 0.193728 0.651983 0.037 Uiso 1 1 calc R U . . .
C3 C 0.4032(2) 0.8781(9) 0.5633(2) 0.0317(11) Uani 1 1 d . . . . .
H3 H 0.392308 1.003630 0.537704 0.038 Uiso 1 1 calc R U . . .
C34 C 0.95749(19) 0.1125(8) 0.4651(2) 0.0295(10) Uani 1 1 d . . . . .
H34A H 0.949198 0.142229 0.509382 0.044 Uiso 1 1 calc R U . . .
H34B H 0.998448 0.128471 0.457682 0.044 Uiso 1 1 calc R U . . .
H34C H 0.945494 -0.043399 0.454274 0.044 Uiso 1 1 calc R U . . .
C20 C 0.82500(19) 0.1220(8) 0.4369(2) 0.0285(10) Uani 1 1 d . . . . .
H20 H 0.834754 -0.003998 0.462965 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5645(2) 0.8432(9) 0.6769(2) 0.0316(11) Uani 1 1 d . . . . .
H15A H 0.536389 0.887793 0.709351 0.038 Uiso 1 1 calc R U . . .
H15B H 0.568659 0.973383 0.647514 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3137(2) 0.2061(8) 0.6770(2) 0.0298(10) Uani 1 1 d . . . . .
H9 H 0.343012 0.127420 0.698697 0.036 Uiso 1 1 calc R U . . .
C1 C 0.47825(19) 0.6578(9) 0.6207(2) 0.0280(10) Uani 1 1 d . . . . .
C19 C 0.76729(19) 0.1622(9) 0.4184(2) 0.0315(11) Uani 1 1 d . . . . .
H19 H 0.738541 0.060082 0.432423 0.038 Uiso 1 1 calc R U . . .
C12 C 0.43753(19) 0.4965(8) 0.6416(2) 0.0262(10) Uani 1 1 d . . . . .
H12 H 0.448744 0.370189 0.666733 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2566(2) 0.1320(9) 0.6821(2) 0.0332(11) Uani 1 1 d . . . . .
H8 H 0.247473 0.004934 0.708005 0.040 Uiso 1 1 calc R U . . .
C2 C 0.4606(2) 0.8455(8) 0.5817(2) 0.0305(10) Uani 1 1 d . . . . .
H2 H 0.488414 0.951754 0.567731 0.037 Uiso 1 1 calc R U . . .
C17 C 0.2714(2) 0.8710(8) 0.5344(2) 0.0305(10) Uani 1 1 d . . . . .
H17A H 0.282882 1.027894 0.544779 0.046 Uiso 1 1 calc R U . . .
H17B H 0.230589 0.852539 0.542431 0.046 Uiso 1 1 calc R U . . .
H17C H 0.279295 0.840647 0.490073 0.046 Uiso 1 1 calc R U . . .
C25 C 0.9761(2) 0.8495(9) 0.3176(2) 0.0327(11) Uani 1 1 d . . . . .
H25 H 0.985492 0.977700 0.292192 0.039 Uiso 1 1 calc R U . . .
C13 C 0.54162(19) 0.6320(8) 0.6405(2) 0.0284(10) Uani 1 1 d . . . . .
H13 H 0.544429 0.495988 0.668919 0.034 Uiso 1 1 calc R U . . .
C30 C 0.68807(19) 0.3929(9) 0.3605(2) 0.0316(10) Uani 1 1 d . . . . .
H30 H 0.686926 0.532605 0.333363 0.038 Uiso 1 1 calc R U . . .
C33 C 0.6061(2) 0.2546(10) 0.2906(2) 0.0353(11) Uani 1 1 d . . . . .
H33A H 0.612081 0.387999 0.263452 0.053 Uiso 1 1 calc R U . . .
H33B H 0.577898 0.292036 0.322830 0.053 Uiso 1 1 calc R U . . .
H33C H 0.592449 0.125551 0.265371 0.053 Uiso 1 1 calc R U . . .
C32 C 0.6628(2) 0.1890(9) 0.3223(3) 0.0353(11) Uani 1 1 d . . . . .
H32A H 0.690398 0.141110 0.289789 0.042 Uiso 1 1 calc R U . . .
H32B H 0.656371 0.057322 0.350717 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C14 1.298(6) . ?
O2 C14 1.225(6) . ?
O4 H4 0.8200 . ?
O4 C31 1.297(6) . ?
O3 C31 1.231(6) . ?
N1 C4 1.381(5) . ?
N1 C5 1.385(6) . ?
N1 C17 1.454(6) . ?
N2 C21 1.386(6) . ?
N2 C22 1.383(6) . ?
N2 C34 1.442(6) . ?
C4 C11 1.412(6) . ?
C4 C3 1.383(7) . ?
C14 C13 1.527(6) . ?
C5 C10 1.418(6) . ?
C5 C6 1.395(6) . ?
C27 C28 1.452(6) . ?
C27 C26 1.388(6) . ?
C27 C22 1.407(6) . ?
C28 C21 1.415(7) . ?
C28 C29 1.397(6) . ?
C23 H23 0.9300 . ?
C23 C22 1.400(6) . ?
C23 C24 1.387(7) . ?
C21 C20 1.388(6) . ?
C26 H26 0.9300 . ?
C26 C25 1.377(7) . ?
C29 H29 0.9300 . ?
C29 C18 1.388(6) . ?
C10 C11 1.440(6) . ?
C10 C9 1.393(7) . ?
C11 C12 1.406(6) . ?
C31 C30 1.520(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C15 1.532(7) . ?
C18 C19 1.384(7) . ?
C18 C30 1.544(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.372(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.407(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.388(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C19 1.403(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C13 1.521(7) . ?
C9 H9 0.9300 . ?
C9 C8 1.384(7) . ?
C1 C12 1.385(7) . ?
C1 C2 1.407(7) . ?
C1 C13 1.524(6) . ?
C19 H19 0.9300 . ?
C12 H12 0.9300 . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C25 H25 0.9300 . ?
C13 H13 0.9800 . ?
C30 H30 0.9800 . ?
C30 C32 1.528(7) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C33 C32 1.509(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 H1 109.5 . . ?
C31 O4 H4 109.5 . . ?
C4 N1 C5 108.8(4) . . ?
C4 N1 C17 125.0(4) . . ?
C5 N1 C17 126.2(4) . . ?
C21 N2 C34 125.2(4) . . ?
C22 N2 C21 108.2(4) . . ?
C22 N2 C34 126.6(4) . . ?
N1 C4 C11 108.9(4) . . ?
N1 C4 C3 129.4(4) . . ?
C3 C4 C11 121.7(4) . . ?
O1 C14 C13 113.2(4) . . ?
O2 C14 O1 123.9(4) . . ?
O2 C14 C13 122.8(4) . . ?
N1 C5 C10 109.1(4) . . ?
N1 C5 C6 129.6(4) . . ?
C6 C5 C10 121.3(4) . . ?
C26 C27 C28 133.2(4) . . ?
C26 C27 C22 120.1(4) . . ?
C22 C27 C28 106.7(4) . . ?
C21 C28 C27 105.8(4) . . ?
C29 C28 C27 133.7(4) . . ?
C29 C28 C21 120.5(4) . . ?
C22 C23 H23 121.4 . . ?
C24 C23 H23 121.4 . . ?
C24 C23 C22 117.2(4) . . ?
N2 C21 C28 109.7(4) . . ?
N2 C21 C20 129.7(4) . . ?
C20 C21 C28 120.5(4) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 C27 119.3(4) . . ?
C25 C26 H26 120.3 . . ?
C28 C29 H29 120.6 . . ?
C18 C29 C28 118.8(4) . . ?
C18 C29 H29 120.6 . . ?
C5 C10 C11 106.1(4) . . ?
C9 C10 C5 119.2(4) . . ?
C9 C10 C11 134.7(4) . . ?
C4 C11 C10 107.1(4) . . ?
C12 C11 C4 119.7(4) . . ?
C12 C11 C10 133.1(4) . . ?
O4 C31 C30 112.7(4) . . ?
O3 C31 O4 124.7(5) . . ?
O3 C31 C30 122.6(5) . . ?
N2 C22 C27 109.6(4) . . ?
N2 C22 C23 129.1(4) . . ?
C23 C22 C27 121.3(4) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
C29 C18 C30 118.2(4) . . ?
C19 C18 C29 120.4(4) . . ?
C19 C18 C30 121.5(4) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 C5 117.8(4) . . ?
C7 C6 H6 121.1 . . ?
C23 C24 H24 119.1 . . ?
C23 C24 C25 121.8(4) . . ?
C25 C24 H24 119.1 . . ?
C6 C7 H7 118.9 . . ?
C6 C7 C8 122.2(5) . . ?
C8 C7 H7 118.9 . . ?
C4 C3 H3 121.3 . . ?
C4 C3 C2 117.3(5) . . ?
C2 C3 H3 121.3 . . ?
N2 C34 H34A 109.5 . . ?
N2 C34 H34B 109.5 . . ?
N2 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C21 C20 H20 121.1 . . ?
C21 C20 C19 117.8(5) . . ?
C19 C20 H20 121.1 . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C13 C15 C16 112.4(4) . . ?
C13 C15 H15A 109.1 . . ?
C13 C15 H15B 109.1 . . ?
C10 C9 H9 120.3 . . ?
C8 C9 C10 119.4(4) . . ?
C8 C9 H9 120.3 . . ?
C12 C1 C2 119.6(4) . . ?
C12 C1 C13 119.9(4) . . ?
C2 C1 C13 120.5(4) . . ?
C18 C19 C20 122.0(4) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C11 C12 H12 120.5 . . ?
C1 C12 C11 119.1(4) . . ?
C1 C12 H12 120.5 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(5) . . ?
C9 C8 H8 119.9 . . ?
C3 C2 C1 122.5(4) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 C25 C24 120.2(4) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C14 C13 H13 107.7 . . ?
C15 C13 C14 112.6(4) . . ?
C15 C13 C1 112.9(4) . . ?
C15 C13 H13 107.7 . . ?
C1 C13 C14 107.9(4) . . ?
C1 C13 H13 107.7 . . ?
C31 C30 C18 107.8(4) . . ?
C31 C30 H30 108.0 . . ?
C31 C30 C32 112.7(4) . . ?
C18 C30 H30 108.0 . . ?
C32 C30 C18 112.2(4) . . ?
C32 C30 H30 108.0 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
C30 C32 H32A 109.3 . . ?
C30 C32 H32B 109.3 . . ?
C33 C32 C30 111.7(4) . . ?
C33 C32 H32A 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C14 C13 C15 148.9(4) . . . . ?
O1 C14 C13 C1 -85.8(5) . . . . ?
O2 C14 C13 C15 -33.8(6) . . . . ?
O2 C14 C13 C1 91.5(5) . . . . ?
O4 C31 C30 C18 90.4(5) . . . . ?
O4 C31 C30 C32 -145.3(4) . . . . ?
O3 C31 C30 C18 -89.6(5) . . . . ?
O3 C31 C30 C32 34.7(6) . . . . ?
N1 C4 C11 C10 -1.2(5) . . . . ?
N1 C4 C11 C12 179.5(4) . . . . ?
N1 C4 C3 C2 179.7(5) . . . . ?
N1 C5 C10 C11 -0.8(5) . . . . ?
N1 C5 C10 C9 177.7(4) . . . . ?
N1 C5 C6 C7 -177.3(5) . . . . ?
N2 C21 C20 C19 -179.8(5) . . . . ?
C4 N1 C5 C10 0.0(5) . . . . ?
C4 N1 C5 C6 179.4(5) . . . . ?
C4 C11 C12 C1 1.5(6) . . . . ?
C4 C3 C2 C1 -0.3(7) . . . . ?
C5 N1 C4 C11 0.8(5) . . . . ?
C5 N1 C4 C3 -178.3(5) . . . . ?
C5 C10 C11 C4 1.2(5) . . . . ?
C5 C10 C11 C12 -179.7(5) . . . . ?
C5 C10 C9 C8 0.1(7) . . . . ?
C5 C6 C7 C8 -0.7(7) . . . . ?
C27 C28 C21 N2 0.8(5) . . . . ?
C27 C28 C21 C20 -178.8(4) . . . . ?
C27 C28 C29 C18 178.9(5) . . . . ?
C27 C26 C25 C24 -0.2(7) . . . . ?
C28 C27 C26 C25 -178.5(5) . . . . ?
C28 C27 C22 N2 0.7(5) . . . . ?
C28 C27 C22 C23 -179.6(4) . . . . ?
C28 C21 C20 C19 -0.3(7) . . . . ?
C28 C29 C18 C19 -0.2(7) . . . . ?
C28 C29 C18 C30 179.7(4) . . . . ?
C23 C24 C25 C26 -1.0(8) . . . . ?
C21 N2 C22 C27 -0.2(5) . . . . ?
C21 N2 C22 C23 -179.9(5) . . . . ?
C21 C28 C29 C18 -0.3(7) . . . . ?
C21 C20 C19 C18 -0.3(7) . . . . ?
C26 C27 C28 C21 177.6(5) . . . . ?
C26 C27 C28 C29 -1.7(9) . . . . ?
C26 C27 C22 N2 -178.0(4) . . . . ?
C26 C27 C22 C23 1.6(7) . . . . ?
C29 C28 C21 N2 -179.8(4) . . . . ?
C29 C28 C21 C20 0.6(7) . . . . ?
C29 C18 C19 C20 0.5(7) . . . . ?
C29 C18 C30 C31 -116.2(5) . . . . ?
C29 C18 C30 C32 119.3(5) . . . . ?
C10 C5 C6 C7 2.0(7) . . . . ?
C10 C11 C12 C1 -177.6(5) . . . . ?
C10 C9 C8 C7 1.2(8) . . . . ?
C11 C4 C3 C2 0.7(7) . . . . ?
C11 C10 C9 C8 178.0(5) . . . . ?
C31 C30 C32 C33 71.4(6) . . . . ?
C22 N2 C21 C28 -0.4(5) . . . . ?
C22 N2 C21 C20 179.2(5) . . . . ?
C22 C27 C28 C21 -0.9(5) . . . . ?
C22 C27 C28 C29 179.8(5) . . . . ?
C22 C27 C26 C25 -0.1(7) . . . . ?
C22 C23 C24 C25 2.4(7) . . . . ?
C16 C15 C13 C14 -70.0(5) . . . . ?
C16 C15 C13 C1 167.5(4) . . . . ?
C18 C30 C32 C33 -166.7(4) . . . . ?
C6 C5 C10 C11 179.8(4) . . . . ?
C6 C5 C10 C9 -1.8(7) . . . . ?
C6 C7 C8 C9 -1.0(8) . . . . ?
C24 C23 C22 N2 176.8(5) . . . . ?
C24 C23 C22 C27 -2.7(7) . . . . ?
C3 C4 C11 C10 178.0(4) . . . . ?
C3 C4 C11 C12 -1.3(7) . . . . ?
C34 N2 C21 C28 178.8(4) . . . . ?
C34 N2 C21 C20 -1.6(8) . . . . ?
C34 N2 C22 C27 -179.4(4) . . . . ?
C34 N2 C22 C23 1.0(8) . . . . ?
C9 C10 C11 C4 -176.9(5) . . . . ?
C9 C10 C11 C12 2.2(9) . . . . ?
C19 C18 C30 C31 63.7(6) . . . . ?
C19 C18 C30 C32 -60.8(6) . . . . ?
C12 C1 C2 C3 0.6(7) . . . . ?
C12 C1 C13 C14 113.9(5) . . . . ?
C12 C1 C13 C15 -121.0(5) . . . . ?
C2 C1 C12 C11 -1.1(6) . . . . ?
C2 C1 C13 C14 -66.6(5) . . . . ?
C2 C1 C13 C15 58.5(6) . . . . ?
C17 N1 C4 C11 -178.8(4) . . . . ?
C17 N1 C4 C3 2.1(7) . . . . ?
C17 N1 C5 C10 179.6(4) . . . . ?
C17 N1 C5 C6 -1.0(8) . . . . ?
C13 C1 C12 C11 178.4(4) . . . . ?
C13 C1 C2 C3 -179.0(4) . . . . ?
C30 C18 C19 C20 -179.4(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.785
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7(5)
2 0.3(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_cd1947
_database_code_depnum_ccdc_archive 'CCDC 1988923'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-03-08 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_audit_creation_date             2020-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O2N1
_chemical_oxdiff_usercomment     'Phenyl Ga-51-3'
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                   7.1570(2)
_cell_length_b                   7.4823(2)
_cell_length_c                   11.6050(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.910(3)
_cell_angle_gamma                90
_cell_volume                     621.38(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5666
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      27.0040
_cell_measurement_theta_min      2.7940
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12259
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.986
_diffrn_reflns_theta_min         2.846
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  34.00   1.00   15.00    --   -7.50 -17.00 101.00  130
  2  ω    -49.00  81.00   1.00   15.00    --   -7.50  17.00 -90.00  130
  3  ω    -32.00  81.00   1.00   15.00    --   -7.50  38.00-180.00  113
  4  ω    -96.00  17.00   1.00   15.00    --   -7.50 -38.00 -30.00  113
  5  ω    -26.00  31.00   1.00   15.00    --    4.20  57.00 -60.00   57
  6  ω    -37.00  81.00   1.00   15.00    --   -7.50  57.00  60.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650784000
_diffrn_orient_matrix_UB_12      -0.0217834000
_diffrn_orient_matrix_UB_13      0.0432924000
_diffrn_orient_matrix_UB_21      -0.0728149000
_diffrn_orient_matrix_UB_22      -0.0019871000
_diffrn_orient_matrix_UB_23      -0.0421272000
_diffrn_orient_matrix_UB_31      0.0169812000
_diffrn_orient_matrix_UB_32      -0.0922524000
_diffrn_orient_matrix_UB_33      -0.0092817000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2315
_reflns_number_total             2413
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;

;
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0371
_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)+(0.0500P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0918
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C8(H8), C9(H9), C6(H6), C12(H12), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4405(2) 0.2933(2) 0.12904(14) 0.0271(4) Uani 1 1 d . . . . .
H1 H 0.474667 0.224334 0.076287 0.041 Uiso 1 1 calc GR . . . .
O2 O 0.4926(3) 0.4997(2) -0.00512(16) 0.0278(4) Uani 1 1 d . . . . .
C5 C 0.7676(3) 0.7075(3) 0.38289(19) 0.0198(5) Uani 1 1 d . . . . .
H5 H 0.873456 0.784199 0.382620 0.024 Uiso 1 1 calc R . . . .
C4 C 0.7357(3) 0.6000(3) 0.47954(19) 0.0171(5) Uani 1 1 d . . . . .
C3 C 0.5766(3) 0.4911(3) 0.4765(2) 0.0207(5) Uani 1 1 d . . . . .
H3 H 0.550361 0.417226 0.540818 0.025 Uiso 1 1 calc R . . . .
C7 C 0.8627(3) 0.6027(3) 0.5824(2) 0.0183(5) Uani 1 1 d . . . . .
C2 C 0.4564(3) 0.4891(3) 0.3813(2) 0.0225(5) Uani 1 1 d . . . . .
H2 H 0.348876 0.414655 0.381946 0.027 Uiso 1 1 calc R . . . .
C1 C 0.4909(3) 0.5944(3) 0.28494(19) 0.0198(5) Uani 1 1 d . . . . .
C14 C 0.4398(3) 0.4598(3) 0.0907(2) 0.0205(5) Uani 1 1 d . . . . .
C8 C 0.8003(3) 0.5484(3) 0.6906(2) 0.0207(5) Uani 1 1 d . . . . .
H8 H 0.675025 0.508830 0.698235 0.025 Uiso 1 1 calc R . . . .
C9 C 0.9175(3) 0.5511(3) 0.7868(2) 0.0241(5) Uani 1 1 d . . . . .
H9 H 0.872443 0.512348 0.859163 0.029 Uiso 1 1 calc R . . . .
C6 C 0.6484(3) 0.7044(3) 0.2879(2) 0.0206(5) Uani 1 1 d . . . . .
H6 H 0.674140 0.778492 0.223594 0.025 Uiso 1 1 calc R . . . .
C15 C 0.1598(3) 0.5517(3) 0.2028(2) 0.0230(5) Uani 1 1 d . . . . .
H15A H 0.151433 0.431857 0.238537 0.028 Uiso 1 1 calc R . . . .
H15B H 0.113050 0.640016 0.258971 0.028 Uiso 1 1 calc R . . . .
C12 C 1.0483(3) 0.6612(3) 0.5749(2) 0.0223(5) Uani 1 1 d . . . . .
H12 H 1.094783 0.698571 0.502510 0.027 Uiso 1 1 calc R . . . .
C13 C 0.3660(3) 0.5931(3) 0.1774(2) 0.0218(5) Uani 1 1 d . . . . .
H13 H 0.371525 0.714554 0.141766 0.026 Uiso 1 1 calc R . . . .
C10 C 1.1003(4) 0.6101(3) 0.7777(2) 0.0243(5) Uani 1 1 d . . . . .
H10 H 1.180544 0.612654 0.843732 0.029 Uiso 1 1 calc R . . . .
C11 C 1.1651(3) 0.6654(3) 0.6715(2) 0.0256(6) Uani 1 1 d . . . . .
H11 H 1.290105 0.706436 0.664866 0.031 Uiso 1 1 calc R . . . .
C16 C 0.0354(3) 0.5564(4) 0.0950(2) 0.0281(6) Uani 1 1 d . . . . .
H16A H 0.076813 0.464808 0.040670 0.042 Uiso 1 1 calc GR . . . .
H16B H 0.043727 0.674385 0.058833 0.042 Uiso 1 1 calc GR . . . .
H16C H -0.094334 0.532859 0.116153 0.042 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C14 1.322(3) . ?
O2 C14 1.218(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.402(3) . ?
C5 C6 1.383(3) . ?
C4 C3 1.400(3) . ?
C4 C7 1.489(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.390(3) . ?
C7 C8 1.399(3) . ?
C7 C12 1.403(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.394(3) . ?
C1 C6 1.396(3) . ?
C1 C13 1.523(3) . ?
C14 C13 1.518(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(4) . ?
C6 H6 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C13 1.541(3) . ?
C15 C16 1.524(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.389(4) . ?
C13 H13 1.0000 . ?
C10 H10 0.9500 . ?
C10 C11 1.387(4) . ?
C11 H11 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 H1 109.5 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.4(2) . . ?
C5 C4 C7 121.9(2) . . ?
C3 C4 C5 117.2(2) . . ?
C3 C4 C7 120.9(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.3 . . ?
C8 C7 C4 121.06(19) . . ?
C8 C7 C12 117.5(2) . . ?
C12 C7 C4 121.4(2) . . ?
C3 C2 H2 119.5 . . ?
C3 C2 C1 121.1(2) . . ?
C1 C2 H2 119.5 . . ?
C2 C1 C6 117.9(2) . . ?
C2 C1 C13 123.0(2) . . ?
C6 C1 C13 119.2(2) . . ?
O1 C14 C13 113.3(2) . . ?
O2 C14 O1 122.6(2) . . ?
O2 C14 C13 124.1(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
H15A C15 H15B 107.8 . . ?
C13 C15 H15A 109.0 . . ?
C13 C15 H15B 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C16 C15 C13 112.8(2) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.0(2) . . ?
C11 C12 H12 119.5 . . ?
C1 C13 C15 113.36(19) . . ?
C1 C13 H13 107.8 . . ?
C14 C13 C1 109.97(19) . . ?
C14 C13 C15 109.8(2) . . ?
C14 C13 H13 107.8 . . ?
C15 C13 H13 107.8 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.047
_oxdiff_exptl_absorpt_empirical_full_min 0.972
