# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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#######################################################################

data_JF2849FMI
_database_code_depnum_ccdc_archive 'CCDC 1916890'
loop_
_audit_author_name
_audit_author_address
'James Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2019-05-18 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 O2'
_chemical_formula_sum            'C28 H24 O2'
_chemical_formula_weight         392.47

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'

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

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

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

_cell_length_a                   9.5034(17)
_cell_length_b                   10.6505(19)
_cell_length_c                   21.889(4)
_cell_angle_alpha                96.945(3)
_cell_angle_beta                 102.069(3)
_cell_angle_gamma                99.440(3)
_cell_volume                     2109.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      30.52

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.781
_exptl_crystal_size_mid          0.652
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8536
_exptl_absorpt_correction_T_max  0.9673
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19292
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0110
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9689
_reflns_number_gt                8901
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
 
 A colorless block with approximate orthogonal dimensions 0.320 x 0.652 x
 0.781mm3 was placed and optically centered on the Bruker Duo(1) APEXII CCD
 system at --183°C(90K).  Indexing of the unit cell used a random set of
 reflections collected from three series of 0.5° wide omega-scans, 5 seconds
 per frame, and 30 frames per series that were well distributed in reciprocal
 space. Six omega-scan data frame series were collected [MoKa] with 0.3° wide
 scans, 15 seconds per frame and 606 frames collected per series at varying f
 angles (f=0°, 60°, 120°, 180°, 240°, 300°). The crystal to detector distance
 was 5.15cm, thus providing a complete sphere of data to 2thetamax=61.09°.
 
;

_computing_data_collection       'Apex2 (2014.9-1) (Bruker, 2014)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Structural determination and Refinement:

All crystallographic calculations were performed on an Intel Xeon E5-1620v2 at
3.70GHz an eight core processor and 16GB of extended memory. Data collected
were corrected for Lorentz and polarization effects with Saint(1) and
absorption using Blessing?s method and merged as incorporated with the program
Sadabs(2,3). The SHELXTL(4) program package was implemented to determine the
probable space group and set up the initial files. System symmetry, lack of
systematic absences and intensity statistics indicated the centrosymmetric
triclinic space group P-1 (no. 2). The structure was determined by direct
methods with a majority of the non-hydrogen atoms for the two molecules being
located directly using the program XT(5). The structure was refined with
XL(6). The data collected were merged for least squares refinement to 9689
unique data [R(int)=0.0110]. Hydrogen atoms were initially calculated and
placed in idealized locations and then allowed to refine freely during the
final cycles of refinement. All non-hydrogen atoms were refined
anisotropically. The final structure was refined to convergence with
R(F)=3.89%, wR(F2)=9.59%, GOF=1.033 for all 8901 unique reflections
[R(F)=3.61, wR(F2)=9.32% for those 8901 data with Fo > 4sigma(Fo). The final
difference-Fourier map was featureless indicating that the structure is both
correct and complete.  An empirical correction for extinction was also
attempted and found to be less than one sigma and therefore not applied.

1.	Bruker (2017) APEX3 (Version 2017.3) and (2017) SAINT (Version 8.38a).
Bruker AXS Inc., Madison, Wisconsin, USA.

2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995).
Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, ?Siemens Area Detector
Absorption Correction? Universität Göttingen: Göttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison,
Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, Universität Göttingen: Göttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2018). SHELXL2018/3. Universität Göttingen: Göttingen,
Germany.

Acknowledgment:  We thank the National Science Foundation (Grant 1531193) for
the Dual source X-ray diffractometer.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+0.7054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9689
_refine_ls_number_parameters     733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.89477(10) 0.94027(9) 0.75550(4) 0.01520(17) Uani 1 1 d . . . . .
H1 H 1.0011(13) 0.9697(11) 0.7770(5) 0.013(3) Uiso 1 1 d . . . . .
O1 O 0.83984(7) 0.82434(6) 0.77731(3) 0.01597(14) Uani 1 1 d . . . . .
C2 C 0.81425(10) 1.04809(9) 0.77467(4) 0.01476(17) Uani 1 1 d . . . . .
H2 H 0.8697(13) 1.1302(11) 0.7669(5) 0.013(3) Uiso 1 1 d . . . . .
C3 C 0.81864(10) 1.05815(9) 0.84487(4) 0.01512(17) Uani 1 1 d . . . . .
C4 C 0.84420(10) 0.95601(9) 0.87768(4) 0.01556(18) Uani 1 1 d . . . . .
C5 C 0.88407(10) 0.83635(9) 0.84472(4) 0.01557(18) Uani 1 1 d . . . . .
H5 H 0.9931(13) 0.8474(11) 0.8570(5) 0.015(3) Uiso 1 1 d . . . . .
C6 C 0.84161(11) 0.96757(9) 0.94180(5) 0.01894(19) Uani 1 1 d . . . . .
H6 H 0.8590(14) 0.8965(13) 0.9650(6) 0.022(3) Uiso 1 1 d . . . . .
C7 C 0.81678(11) 1.08034(10) 0.97336(5) 0.02039(19) Uani 1 1 d . . . . .
H7 H 0.8146(14) 1.0885(12) 1.0178(6) 0.023(3) Uiso 1 1 d . . . . .
C8 C 0.79338(11) 1.18269(9) 0.94092(5) 0.01973(19) Uani 1 1 d . . . . .
H8 H 0.7755(15) 1.2622(13) 0.9631(6) 0.026(3) Uiso 1 1 d . . . . .
C9 C 0.79280(10) 1.17076(9) 0.87703(5) 0.01745(18) Uani 1 1 d . . . . .
H9 H 0.7731(14) 1.2400(12) 0.8530(6) 0.021(3) Uiso 1 1 d . . . . .
C10 C 0.88013(10) 0.91010(9) 0.68504(4) 0.01572(18) Uani 1 1 d . . . . .
C11 C 0.97411(11) 0.98573(10) 0.65677(5) 0.01950(19) Uani 1 1 d . . . . .
H11 H 1.0508(15) 1.0556(13) 0.6833(6) 0.025(3) Uiso 1 1 d . . . . .
C12 C 0.96347(11) 0.96154(10) 0.59211(5) 0.0220(2) Uani 1 1 d . . . . .
H12 H 1.0293(16) 1.0128(14) 0.5722(7) 0.032(4) Uiso 1 1 d . . . . .
C13 C 0.85874(11) 0.85877(10) 0.55463(5) 0.02016(19) Uani 1 1 d . . . . .
O13 O 0.85951(9) 0.84007(8) 0.49139(4) 0.03015(18) Uani 1 1 d . . . . .
C14 C 0.76301(11) 0.78291(10) 0.58168(5) 0.02032(19) Uani 1 1 d . . . . .
H14 H 0.6884(15) 0.7121(13) 0.5560(6) 0.028(3) Uiso 1 1 d . . . . .
C15 C 0.77370(11) 0.81013(9) 0.64673(5) 0.01849(19) Uani 1 1 d . . . . .
H15 H 0.7065(15) 0.7567(13) 0.6657(6) 0.027(3) Uiso 1 1 d . . . . .
C16 C 0.77865(14) 0.72102(12) 0.45435(5) 0.0314(3) Uani 1 1 d . . . . .
H16A H 0.8147(17) 0.6487(15) 0.4734(7) 0.037(4) Uiso 1 1 d . . . . .
H16B H 0.7986(18) 0.7222(15) 0.4116(8) 0.043(4) Uiso 1 1 d . . . . .
H16C H 0.6720(17) 0.7143(14) 0.4510(7) 0.037(4) Uiso 1 1 d . . . . .
C17 C 0.65736(10) 1.02994(9) 0.73575(4) 0.01552(18) Uani 1 1 d . . . . .
C18 C 0.62215(11) 1.11036(11) 0.69161(5) 0.0228(2) Uani 1 1 d . . . . .
H18 H 0.6978(16) 1.1777(14) 0.6870(7) 0.031(3) Uiso 1 1 d . . . . .
C19 C 0.47947(12) 1.09476(12) 0.65515(5) 0.0290(2) Uani 1 1 d . . . . .
H19 H 0.4570(17) 1.1540(15) 0.6250(7) 0.038(4) Uiso 1 1 d . . . . .
C20 C 0.37032(12) 0.99829(11) 0.66237(5) 0.0259(2) Uani 1 1 d . . . . .
H20 H 0.2696(16) 0.9876(13) 0.6367(7) 0.031(4) Uiso 1 1 d . . . . .
C21 C 0.40369(11) 0.91761(10) 0.70627(5) 0.0225(2) Uani 1 1 d . . . . .
H21 H 0.3274(16) 0.8498(14) 0.7116(7) 0.030(3) Uiso 1 1 d . . . . .
C22 C 0.54570(11) 0.93372(9) 0.74302(5) 0.01913(19) Uani 1 1 d . . . . .
H22 H 0.5673(15) 0.8773(13) 0.7751(6) 0.025(3) Uiso 1 1 d . . . . .
C23 C 0.81683(10) 0.71171(9) 0.86311(4) 0.01579(18) Uani 1 1 d . . . . .
C24 C 0.67310(11) 0.65022(10) 0.83410(5) 0.0215(2) Uani 1 1 d . . . . .
H24 H 0.6157(15) 0.6858(13) 0.8007(6) 0.028(3) Uiso 1 1 d . . . . .
C25 C 0.61092(12) 0.53811(10) 0.85285(5) 0.0246(2) Uani 1 1 d . . . . .
H25 H 0.5079(17) 0.4952(14) 0.8323(7) 0.036(4) Uiso 1 1 d . . . . .
C26 C 0.69091(12) 0.48630(10) 0.90086(5) 0.0218(2) Uani 1 1 d . . . . .
H26 H 0.6441(16) 0.4095(14) 0.9145(7) 0.031(3) Uiso 1 1 d . . . . .
C27 C 0.83452(12) 0.54602(10) 0.92942(5) 0.0233(2) Uani 1 1 d . . . . .
H27 H 0.8927(15) 0.5100(13) 0.9634(7) 0.031(4) Uiso 1 1 d . . . . .
C28 C 0.89792(11) 0.65777(9) 0.91033(5) 0.02001(19) Uani 1 1 d . . . . .
H28 H 1.0005(15) 0.6990(13) 0.9294(6) 0.028(3) Uiso 1 1 d . . . . .
C31 C 1.03115(10) 0.53256(9) 0.24186(5) 0.01681(18) Uani 1 1 d . . . . .
H31 H 1.0949(13) 0.5198(11) 0.2118(6) 0.016(3) Uiso 1 1 d . . . . .
O31 O 0.95089(7) 0.63035(6) 0.22422(3) 0.01804(14) Uani 1 1 d . . . . .
C32 C 0.92291(10) 0.40323(9) 0.23558(5) 0.01618(18) Uani 1 1 d . . . . .
H32 H 0.9830(14) 0.3349(12) 0.2382(6) 0.021(3) Uiso 1 1 d . . . . .
C33 C 0.81633(10) 0.37696(9) 0.17097(4) 0.01642(18) Uani 1 1 d . . . . .
C34 C 0.79771(10) 0.47457(9) 0.13434(4) 0.01639(18) Uani 1 1 d . . . . .
C35 C 0.88596(10) 0.61159(9) 0.15807(5) 0.01721(18) Uani 1 1 d . . . . .
H35 H 0.9660(14) 0.6261(12) 0.1346(6) 0.024(3) Uiso 1 1 d . . . . .
C36 C 0.69784(11) 0.44656(10) 0.07521(5) 0.02016(19) Uani 1 1 d . . . . .
H36 H 0.6857(15) 0.5152(13) 0.0497(6) 0.027(3) Uiso 1 1 d . . . . .
C37 C 0.61447(12) 0.32349(10) 0.05301(5) 0.0228(2) Uani 1 1 d . . . . .
H37 H 0.5442(16) 0.3059(14) 0.0119(7) 0.034(4) Uiso 1 1 d . . . . .
C38 C 0.63122(12) 0.22625(10) 0.08971(5) 0.0227(2) Uani 1 1 d . . . . .
H38 H 0.5712(15) 0.1398(14) 0.0744(6) 0.028(3) Uiso 1 1 d . . . . .
C39 C 0.73153(11) 0.25287(9) 0.14789(5) 0.01946(19) Uani 1 1 d . . . . .
H39 H 0.7426(14) 0.1856(13) 0.1740(6) 0.022(3) Uiso 1 1 d . . . . .
C40 C 1.12443(10) 0.58119(9) 0.30788(5) 0.01725(18) Uani 1 1 d . . . . .
C41 C 1.25232(11) 0.53477(10) 0.32886(5) 0.0211(2) Uani 1 1 d . . . . .
H41 H 1.2781(15) 0.4682(14) 0.3002(7) 0.029(3) Uiso 1 1 d . . . . .
C42 C 1.34108(11) 0.58101(10) 0.38886(5) 0.0230(2) Uani 1 1 d . . . . .
H42 H 1.4328(16) 0.5516(14) 0.4036(7) 0.034(4) Uiso 1 1 d . . . . .
C43 C 1.30518(11) 0.67725(10) 0.42860(5) 0.02018(19) Uani 1 1 d . . . . .
O43 O 1.40581(9) 0.72336(8) 0.48505(4) 0.02621(17) Uani 1 1 d . . . . .
C44 C 1.17555(11) 0.72133(10) 0.40934(5) 0.0208(2) Uani 1 1 d . . . . .
H44 H 1.1479(15) 0.7883(13) 0.4370(6) 0.026(3) Uiso 1 1 d . . . . .
C45 C 1.08602(11) 0.67224(10) 0.34933(5) 0.01959(19) Uani 1 1 d . . . . .
H45 H 0.9979(15) 0.7037(13) 0.3351(6) 0.027(3) Uiso 1 1 d . . . . .
C46 C 1.38984(14) 0.84047(11) 0.52014(6) 0.0293(2) Uani 1 1 d . . . . .
H46A H 1.3832(16) 0.9101(15) 0.4928(7) 0.037(4) Uiso 1 1 d . . . . .
H46B H 1.4763(17) 0.8632(14) 0.5553(7) 0.038(4) Uiso 1 1 d . . . . .
H46C H 1.2998(17) 0.8279(14) 0.5368(7) 0.034(4) Uiso 1 1 d . . . . .
C47 C 0.84429(10) 0.40088(9) 0.28944(4) 0.01624(18) Uani 1 1 d . . . . .
C48 C 0.90850(11) 0.36295(10) 0.34611(5) 0.02029(19) Uani 1 1 d . . . . .
H48 H 1.0010(16) 0.3364(13) 0.3506(6) 0.029(3) Uiso 1 1 d . . . . .
C49 C 0.83977(12) 0.36403(10) 0.39635(5) 0.0244(2) Uani 1 1 d . . . . .
H49 H 0.8873(16) 0.3359(14) 0.4355(7) 0.032(4) Uiso 1 1 d . . . . .
C50 C 0.70458(13) 0.40131(11) 0.39057(5) 0.0256(2) Uani 1 1 d . . . . .
H50 H 0.6552(16) 0.4006(14) 0.4254(7) 0.032(4) Uiso 1 1 d . . . . .
C51 C 0.63963(12) 0.43818(11) 0.33441(5) 0.0245(2) Uani 1 1 d . . . . .
H51 H 0.5438(17) 0.4637(14) 0.3288(7) 0.035(4) Uiso 1 1 d . . . . .
C52 C 0.70912(11) 0.43852(10) 0.28432(5) 0.01947(19) Uani 1 1 d . . . . .
H52 H 0.6616(14) 0.4645(12) 0.2445(6) 0.022(3) Uiso 1 1 d . . . . .
C53 C 0.79148(10) 0.71222(9) 0.14816(5) 0.01740(18) Uani 1 1 d . . . . .
C54 C 0.70406(11) 0.73761(9) 0.19039(5) 0.01967(19) Uani 1 1 d . . . . .
H54 H 0.7106(13) 0.6940(12) 0.2281(6) 0.019(3) Uiso 1 1 d . . . . .
C55 C 0.60938(12) 0.82349(10) 0.17991(5) 0.0232(2) Uani 1 1 d . . . . .
H55 H 0.5487(15) 0.8406(13) 0.2096(7) 0.029(3) Uiso 1 1 d . . . . .
C56 C 0.60159(12) 0.88551(10) 0.12719(6) 0.0253(2) Uani 1 1 d . . . . .
H56 H 0.5338(16) 0.9452(14) 0.1191(7) 0.031(4) Uiso 1 1 d . . . . .
C57 C 0.69014(12) 0.86261(10) 0.08559(5) 0.0260(2) Uani 1 1 d . . . . .
H57 H 0.6860(16) 0.9063(14) 0.0489(7) 0.032(4) Uiso 1 1 d . . . . .
C58 C 0.78568(12) 0.77666(10) 0.09616(5) 0.0225(2) Uani 1 1 d . . . . .
H58 H 0.8486(15) 0.7614(13) 0.0672(6) 0.027(3) Uiso 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
C1 O1 1.4353(11) . ?
C1 C10 1.5090(13) . ?
C1 C2 1.5447(12) . ?
C1 H1 1.002(12) . ?
O1 C5 1.4309(11) . ?
C2 C3 1.5187(13) . ?
C2 C17 1.5234(13) . ?
C2 H2 0.997(12) . ?
C3 C9 1.3996(13) . ?
C3 C4 1.4001(13) . ?
C4 C6 1.3999(13) . ?
C4 C5 1.5292(12) . ?
C5 C23 1.5135(13) . ?
C5 H5 0.998(12) . ?
C6 C7 1.3913(14) . ?
C6 H6 0.979(13) . ?
C7 C8 1.3937(14) . ?
C7 H7 0.970(13) . ?
C8 C9 1.3876(14) . ?
C8 H8 0.982(14) . ?
C9 H9 0.977(13) . ?
C10 C15 1.3914(14) . ?
C10 C11 1.3946(13) . ?
C11 C12 1.3868(14) . ?
C11 H11 0.982(14) . ?
C12 C13 1.3949(15) . ?
C12 H12 0.969(15) . ?
C13 O13 1.3760(12) . ?
C13 C14 1.3896(14) . ?
O13 C16 1.4237(14) . ?
C14 C15 1.3971(14) . ?
C14 H14 0.971(14) . ?
C15 H15 0.976(14) . ?
C16 H16A 0.995(16) . ?
C16 H16B 0.995(16) . ?
C16 H16C 0.991(16) . ?
C17 C18 1.3921(14) . ?
C17 C22 1.3981(13) . ?
C18 C19 1.3944(15) . ?
C18 H18 0.960(15) . ?
C19 C20 1.3837(17) . ?
C19 H19 0.983(15) . ?
C20 C21 1.3869(16) . ?
C20 H20 0.984(14) . ?
C21 C22 1.3909(14) . ?
C21 H21 0.971(15) . ?
C22 H22 0.990(13) . ?
C23 C24 1.3933(14) . ?
C23 C28 1.3956(13) . ?
C24 C25 1.3899(14) . ?
C24 H24 0.972(14) . ?
C25 C26 1.3894(15) . ?
C25 H25 0.995(16) . ?
C26 C27 1.3858(16) . ?
C26 H26 0.976(15) . ?
C27 C28 1.3944(15) . ?
C27 H27 0.987(14) . ?
C28 H28 0.981(14) . ?
C31 O31 1.4319(11) . ?
C31 C40 1.5085(13) . ?
C31 C32 1.5506(13) . ?
C31 H31 0.995(12) . ?
O31 C35 1.4260(12) . ?
C32 C33 1.5219(13) . ?
C32 C47 1.5226(13) . ?
C32 H32 0.996(13) . ?
C33 C34 1.3990(13) . ?
C33 C39 1.4037(13) . ?
C34 C36 1.4019(14) . ?
C34 C35 1.5283(13) . ?
C35 C53 1.5141(13) . ?
C35 H35 1.006(13) . ?
C36 C37 1.3879(14) . ?
C36 H36 0.979(14) . ?
C37 C38 1.3946(15) . ?
C37 H37 0.978(15) . ?
C38 C39 1.3884(15) . ?
C38 H38 0.979(14) . ?
C39 H39 0.975(13) . ?
C40 C45 1.3923(13) . ?
C40 C41 1.3968(14) . ?
C41 C42 1.3867(15) . ?
C41 H41 0.985(14) . ?
C42 C43 1.3954(14) . ?
C42 H42 0.979(15) . ?
C43 O43 1.3738(12) . ?
C43 C44 1.3914(14) . ?
O43 C46 1.4309(14) . ?
C44 C45 1.3941(14) . ?
C44 H44 0.984(14) . ?
C45 H45 0.959(14) . ?
C46 H46A 1.008(15) . ?
C46 H46B 0.976(16) . ?
C46 H46C 0.994(15) . ?
C47 C52 1.3939(13) . ?
C47 C48 1.3999(14) . ?
C48 C49 1.3914(15) . ?
C48 H48 0.956(14) . ?
C49 C50 1.3914(16) . ?
C49 H49 0.986(14) . ?
C50 C51 1.3876(16) . ?
C50 H50 0.975(15) . ?
C51 C52 1.3931(14) . ?
C51 H51 0.981(15) . ?
C52 H52 0.988(13) . ?
C53 C58 1.3946(14) . ?
C53 C54 1.3972(14) . ?
C54 C55 1.3904(14) . ?
C54 H54 0.990(12) . ?
C55 C56 1.3923(16) . ?
C55 H55 0.974(14) . ?
C56 C57 1.3894(16) . ?
C56 H56 0.982(14) . ?
C57 C58 1.3971(15) . ?
C57 H57 0.972(15) . ?
C58 H58 0.976(14) . ?

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 C10 108.54(7) . . ?
O1 C1 C2 109.94(7) . . ?
C10 C1 C2 113.46(7) . . ?
O1 C1 H1 108.5(7) . . ?
C10 C1 H1 109.0(7) . . ?
C2 C1 H1 107.3(7) . . ?
C5 O1 C1 111.57(7) . . ?
C3 C2 C17 111.05(7) . . ?
C3 C2 C1 109.03(7) . . ?
C17 C2 C1 113.56(8) . . ?
C3 C2 H2 108.8(7) . . ?
C17 C2 H2 107.3(7) . . ?
C1 C2 H2 106.8(7) . . ?
C9 C3 C4 119.36(9) . . ?
C9 C3 C2 119.20(8) . . ?
C4 C3 C2 121.42(8) . . ?
C6 C4 C3 119.49(9) . . ?
C6 C4 C5 120.28(8) . . ?
C3 C4 C5 120.12(8) . . ?
O1 C5 C23 107.55(7) . . ?
O1 C5 C4 111.53(7) . . ?
C23 C5 C4 113.59(8) . . ?
O1 C5 H5 108.3(7) . . ?
C23 C5 H5 108.8(7) . . ?
C4 C5 H5 106.9(7) . . ?
C7 C6 C4 120.60(9) . . ?
C7 C6 H6 119.4(8) . . ?
C4 C6 H6 120.0(8) . . ?
C6 C7 C8 119.90(9) . . ?
C6 C7 H7 120.8(8) . . ?
C8 C7 H7 119.3(8) . . ?
C9 C8 C7 119.74(9) . . ?
C9 C8 H8 120.2(8) . . ?
C7 C8 H8 120.0(8) . . ?
C8 C9 C3 120.88(9) . . ?
C8 C9 H9 121.1(7) . . ?
C3 C9 H9 118.0(7) . . ?
C15 C10 C11 118.46(9) . . ?
C15 C10 C1 122.13(8) . . ?
C11 C10 C1 119.40(8) . . ?
C12 C11 C10 121.10(9) . . ?
C12 C11 H11 119.6(8) . . ?
C10 C11 H11 119.3(8) . . ?
C11 C12 C13 119.71(9) . . ?
C11 C12 H12 121.6(9) . . ?
C13 C12 H12 118.7(9) . . ?
O13 C13 C14 124.36(9) . . ?
O13 C13 C12 115.47(9) . . ?
C14 C13 C12 120.17(9) . . ?
C13 O13 C16 117.11(8) . . ?
C13 C14 C15 119.29(9) . . ?
C13 C14 H14 120.9(8) . . ?
C15 C14 H14 119.8(8) . . ?
C10 C15 C14 121.23(9) . . ?
C10 C15 H15 119.5(8) . . ?
C14 C15 H15 119.2(8) . . ?
O13 C16 H16A 109.1(9) . . ?
O13 C16 H16B 105.5(9) . . ?
H16A C16 H16B 110.7(13) . . ?
O13 C16 H16C 111.1(9) . . ?
H16A C16 H16C 111.2(13) . . ?
H16B C16 H16C 109.1(12) . . ?
C18 C17 C22 118.31(9) . . ?
C18 C17 C2 120.00(8) . . ?
C22 C17 C2 121.70(8) . . ?
C17 C18 C19 120.91(10) . . ?
C17 C18 H18 118.7(9) . . ?
C19 C18 H18 120.3(8) . . ?
C20 C19 C18 120.18(10) . . ?
C20 C19 H19 120.5(9) . . ?
C18 C19 H19 119.3(9) . . ?
C19 C20 C21 119.56(10) . . ?
C19 C20 H20 120.1(8) . . ?
C21 C20 H20 120.4(8) . . ?
C20 C21 C22 120.32(10) . . ?
C20 C21 H21 119.9(8) . . ?
C22 C21 H21 119.8(8) . . ?
C21 C22 C17 120.71(9) . . ?
C21 C22 H22 119.5(8) . . ?
C17 C22 H22 119.8(8) . . ?
C24 C23 C28 119.02(9) . . ?
C24 C23 C5 120.83(8) . . ?
C28 C23 C5 120.15(9) . . ?
C25 C24 C23 120.31(9) . . ?
C25 C24 H24 119.6(8) . . ?
C23 C24 H24 120.0(8) . . ?
C26 C25 C24 120.50(10) . . ?
C26 C25 H25 119.6(9) . . ?
C24 C25 H25 119.9(9) . . ?
C27 C26 C25 119.54(10) . . ?
C27 C26 H26 121.1(8) . . ?
C25 C26 H26 119.3(8) . . ?
C26 C27 C28 120.18(9) . . ?
C26 C27 H27 120.4(8) . . ?
C28 C27 H27 119.5(8) . . ?
C27 C28 C23 120.43(9) . . ?
C27 C28 H28 120.6(8) . . ?
C23 C28 H28 118.9(8) . . ?
O31 C31 C40 107.15(7) . . ?
O31 C31 C32 109.62(7) . . ?
C40 C31 C32 113.98(8) . . ?
O31 C31 H31 108.4(7) . . ?
C40 C31 H31 109.9(7) . . ?
C32 C31 H31 107.6(7) . . ?
C35 O31 C31 112.89(7) . . ?
C33 C32 C47 112.25(8) . . ?
C33 C32 C31 109.10(8) . . ?
C47 C32 C31 112.31(8) . . ?
C33 C32 H32 108.9(7) . . ?
C47 C32 H32 107.5(7) . . ?
C31 C32 H32 106.6(7) . . ?
C34 C33 C39 118.79(9) . . ?
C34 C33 C32 121.58(8) . . ?
C39 C33 C32 119.61(9) . . ?
C33 C34 C36 119.83(9) . . ?
C33 C34 C35 120.58(8) . . ?
C36 C34 C35 119.60(8) . . ?
O31 C35 C53 106.56(7) . . ?
O31 C35 C34 111.45(8) . . ?
C53 C35 C34 112.15(8) . . ?
O31 C35 H35 108.9(7) . . ?
C53 C35 H35 109.5(7) . . ?
C34 C35 H35 108.3(7) . . ?
C37 C36 C34 120.78(9) . . ?
C37 C36 H36 119.8(8) . . ?
C34 C36 H36 119.4(8) . . ?
C36 C37 C38 119.61(10) . . ?
C36 C37 H37 119.7(9) . . ?
C38 C37 H37 120.7(9) . . ?
C39 C38 C37 119.90(9) . . ?
C39 C38 H38 120.5(8) . . ?
C37 C38 H38 119.6(8) . . ?
C38 C39 C33 121.08(9) . . ?
C38 C39 H39 120.2(8) . . ?
C33 C39 H39 118.7(8) . . ?
C45 C40 C41 118.39(9) . . ?
C45 C40 C31 121.45(9) . . ?
C41 C40 C31 120.16(9) . . ?
C42 C41 C40 120.78(9) . . ?
C42 C41 H41 120.6(8) . . ?
C40 C41 H41 118.6(8) . . ?
C41 C42 C43 120.12(9) . . ?
C41 C42 H42 121.7(9) . . ?
C43 C42 H42 118.1(9) . . ?
O43 C43 C44 124.60(9) . . ?
O43 C43 C42 115.60(9) . . ?
C44 C43 C42 119.80(9) . . ?
C43 O43 C46 116.81(9) . . ?
C43 C44 C45 119.36(9) . . ?
C43 C44 H44 120.8(8) . . ?
C45 C44 H44 119.8(8) . . ?
C40 C45 C44 121.41(9) . . ?
C40 C45 H45 118.4(8) . . ?
C44 C45 H45 120.1(8) . . ?
O43 C46 H46A 111.1(9) . . ?
O43 C46 H46B 105.0(9) . . ?
H46A C46 H46B 112.0(12) . . ?
O43 C46 H46C 111.5(9) . . ?
H46A C46 H46C 107.7(12) . . ?
H46B C46 H46C 109.6(12) . . ?
C52 C47 C48 118.40(9) . . ?
C52 C47 C32 121.32(9) . . ?
C48 C47 C32 120.27(9) . . ?
C49 C48 C47 120.81(10) . . ?
C49 C48 H48 119.4(8) . . ?
C47 C48 H48 119.8(8) . . ?
C50 C49 C48 120.24(10) . . ?
C50 C49 H49 120.9(8) . . ?
C48 C49 H49 118.9(8) . . ?
C51 C50 C49 119.34(10) . . ?
C51 C50 H50 120.2(8) . . ?
C49 C50 H50 120.5(8) . . ?
C50 C51 C52 120.47(10) . . ?
C50 C51 H51 121.1(9) . . ?
C52 C51 H51 118.4(9) . . ?
C51 C52 C47 120.74(9) . . ?
C51 C52 H52 119.7(7) . . ?
C47 C52 H52 119.5(7) . . ?
C58 C53 C54 119.23(9) . . ?
C58 C53 C35 121.14(9) . . ?
C54 C53 C35 119.59(9) . . ?
C55 C54 C53 120.52(9) . . ?
C55 C54 H54 120.3(7) . . ?
C53 C54 H54 119.2(7) . . ?
C54 C55 C56 120.05(10) . . ?
C54 C55 H55 120.0(8) . . ?
C56 C55 H55 120.0(8) . . ?
C57 C56 C55 119.78(10) . . ?
C57 C56 H56 119.7(8) . . ?
C55 C56 H56 120.5(8) . . ?
C56 C57 C58 120.24(10) . . ?
C56 C57 H57 120.2(9) . . ?
C58 C57 H57 119.6(9) . . ?
C53 C58 C57 120.15(10) . . ?
C53 C58 H58 119.7(8) . . ?
C57 C58 H58 120.1(8) . . ?

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
C10 C1 O1 C5 164.91(7) . . . . ?
C2 C1 O1 C5 -70.46(9) . . . . ?
O1 C1 C2 C3 50.72(10) . . . . ?
C10 C1 C2 C3 172.47(7) . . . . ?
O1 C1 C2 C17 -73.67(10) . . . . ?
C10 C1 C2 C17 48.08(10) . . . . ?
C17 C2 C3 C9 -72.94(10) . . . . ?
C1 C2 C3 C9 161.19(8) . . . . ?
C17 C2 C3 C4 105.38(10) . . . . ?
C1 C2 C3 C4 -20.48(11) . . . . ?
C9 C3 C4 C6 0.82(14) . . . . ?
C2 C3 C4 C6 -177.51(8) . . . . ?
C9 C3 C4 C5 -175.38(8) . . . . ?
C2 C3 C4 C5 6.30(13) . . . . ?
C1 O1 C5 C23 178.09(7) . . . . ?
C1 O1 C5 C4 52.93(10) . . . . ?
C6 C4 C5 O1 162.95(8) . . . . ?
C3 C4 C5 O1 -20.88(12) . . . . ?
C6 C4 C5 C23 41.22(12) . . . . ?
C3 C4 C5 C23 -142.61(9) . . . . ?
C3 C4 C6 C7 -1.27(14) . . . . ?
C5 C4 C6 C7 174.93(9) . . . . ?
C4 C6 C7 C8 0.37(15) . . . . ?
C6 C7 C8 C9 0.97(15) . . . . ?
C7 C8 C9 C3 -1.42(15) . . . . ?
C4 C3 C9 C8 0.52(14) . . . . ?
C2 C3 C9 C8 178.88(9) . . . . ?
O1 C1 C10 C15 26.90(12) . . . . ?
C2 C1 C10 C15 -95.62(11) . . . . ?
O1 C1 C10 C11 -154.26(8) . . . . ?
C2 C1 C10 C11 83.22(11) . . . . ?
C15 C10 C11 C12 -0.71(15) . . . . ?
C1 C10 C11 C12 -179.59(9) . . . . ?
C10 C11 C12 C13 -1.00(16) . . . . ?
C11 C12 C13 O13 -178.11(9) . . . . ?
C11 C12 C13 C14 1.61(16) . . . . ?
C14 C13 O13 C16 -13.47(16) . . . . ?
C12 C13 O13 C16 166.24(10) . . . . ?
O13 C13 C14 C15 179.20(10) . . . . ?
C12 C13 C14 C15 -0.50(15) . . . . ?
C11 C10 C15 C14 1.85(14) . . . . ?
C1 C10 C15 C14 -179.30(9) . . . . ?
C13 C14 C15 C10 -1.25(15) . . . . ?
C3 C2 C17 C18 128.24(9) . . . . ?
C1 C2 C17 C18 -108.46(10) . . . . ?
C3 C2 C17 C22 -51.71(11) . . . . ?
C1 C2 C17 C22 71.59(11) . . . . ?
C22 C17 C18 C19 -0.54(15) . . . . ?
C2 C17 C18 C19 179.50(10) . . . . ?
C17 C18 C19 C20 -0.11(18) . . . . ?
C18 C19 C20 C21 0.25(17) . . . . ?
C19 C20 C21 C22 0.26(16) . . . . ?
C20 C21 C22 C17 -0.93(15) . . . . ?
C18 C17 C22 C21 1.05(14) . . . . ?
C2 C17 C22 C21 -178.99(9) . . . . ?
O1 C5 C23 C24 -41.37(11) . . . . ?
C4 C5 C23 C24 82.55(11) . . . . ?
O1 C5 C23 C28 139.62(9) . . . . ?
C4 C5 C23 C28 -96.45(10) . . . . ?
C28 C23 C24 C25 1.16(15) . . . . ?
C5 C23 C24 C25 -177.86(9) . . . . ?
C23 C24 C25 C26 0.28(17) . . . . ?
C24 C25 C26 C27 -1.05(17) . . . . ?
C25 C26 C27 C28 0.38(16) . . . . ?
C26 C27 C28 C23 1.08(16) . . . . ?
C24 C23 C28 C27 -1.84(15) . . . . ?
C5 C23 C28 C27 177.19(9) . . . . ?
C40 C31 O31 C35 165.67(7) . . . . ?
C32 C31 O31 C35 -70.17(9) . . . . ?
O31 C31 C32 C33 49.41(10) . . . . ?
C40 C31 C32 C33 169.48(8) . . . . ?
O31 C31 C32 C47 -75.70(10) . . . . ?
C40 C31 C32 C47 44.37(11) . . . . ?
C47 C32 C33 C34 108.11(10) . . . . ?
C31 C32 C33 C34 -17.03(12) . . . . ?
C47 C32 C33 C39 -70.26(11) . . . . ?
C31 C32 C33 C39 164.60(8) . . . . ?
C39 C33 C34 C36 -1.28(13) . . . . ?
C32 C33 C34 C36 -179.66(8) . . . . ?
C39 C33 C34 C35 179.04(8) . . . . ?
C32 C33 C34 C35 0.66(13) . . . . ?
C31 O31 C35 C53 173.54(7) . . . . ?
C31 O31 C35 C34 50.90(10) . . . . ?
C33 C34 C35 O31 -15.77(12) . . . . ?
C36 C34 C35 O31 164.55(8) . . . . ?
C33 C34 C35 C53 -135.15(9) . . . . ?
C36 C34 C35 C53 45.17(12) . . . . ?
C33 C34 C36 C37 1.43(14) . . . . ?
C35 C34 C36 C37 -178.89(9) . . . . ?
C34 C36 C37 C38 -0.58(15) . . . . ?
C36 C37 C38 C39 -0.39(16) . . . . ?
C37 C38 C39 C33 0.52(15) . . . . ?
C34 C33 C39 C38 0.32(14) . . . . ?
C32 C33 C39 C38 178.73(9) . . . . ?
O31 C31 C40 C45 24.83(12) . . . . ?
C32 C31 C40 C45 -96.62(11) . . . . ?
O31 C31 C40 C41 -155.36(9) . . . . ?
C32 C31 C40 C41 83.19(11) . . . . ?
C45 C40 C41 C42 -1.84(15) . . . . ?
C31 C40 C41 C42 178.35(9) . . . . ?
C40 C41 C42 C43 -1.54(16) . . . . ?
C41 C42 C43 O43 -175.21(9) . . . . ?
C41 C42 C43 C44 3.79(16) . . . . ?
C44 C43 O43 C46 -12.78(15) . . . . ?
C42 C43 O43 C46 166.16(10) . . . . ?
O43 C43 C44 C45 176.30(9) . . . . ?
C42 C43 C44 C45 -2.60(15) . . . . ?
C41 C40 C45 C44 3.05(15) . . . . ?
C31 C40 C45 C44 -177.15(9) . . . . ?
C43 C44 C45 C40 -0.84(15) . . . . ?
C33 C32 C47 C52 -31.26(12) . . . . ?
C31 C32 C47 C52 92.10(11) . . . . ?
C33 C32 C47 C48 150.04(9) . . . . ?
C31 C32 C47 C48 -86.59(11) . . . . ?
C52 C47 C48 C49 -0.64(14) . . . . ?
C32 C47 C48 C49 178.09(9) . . . . ?
C47 C48 C49 C50 0.91(16) . . . . ?
C48 C49 C50 C51 -0.43(16) . . . . ?
C49 C50 C51 C52 -0.29(17) . . . . ?
C50 C51 C52 C47 0.56(16) . . . . ?
C48 C47 C52 C51 -0.09(15) . . . . ?
C32 C47 C52 C51 -178.81(9) . . . . ?
O31 C35 C53 C58 139.94(9) . . . . ?
C34 C35 C53 C58 -97.85(11) . . . . ?
O31 C35 C53 C54 -42.58(11) . . . . ?
C34 C35 C53 C54 79.62(11) . . . . ?
C58 C53 C54 C55 1.71(15) . . . . ?
C35 C53 C54 C55 -175.81(9) . . . . ?
C53 C54 C55 C56 -0.32(15) . . . . ?
C54 C55 C56 C57 -0.87(16) . . . . ?
C55 C56 C57 C58 0.67(17) . . . . ?
C54 C53 C58 C57 -1.91(15) . . . . ?
C35 C53 C58 C57 175.58(9) . . . . ?
C56 C57 C58 C53 0.73(16) . . . . ?

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
_geom_hbond_publ_flag
C12 H12 O13 0.969(15) 2.472(15) 3.4189(13) 165.6(12) 2_776 yes

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_JF2822FMI
_database_code_depnum_ccdc_archive 'CCDC 1921673'
loop_
_audit_author_name
_audit_author_address
'James Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 O'
_chemical_formula_sum            'C23 H20 O'
_chemical_formula_weight         312.39

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 2'
_space_group_name_Hall           'I 2y'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   17.3724(8)
_cell_length_b                   5.5677(3)
_cell_length_c                   18.8919(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.6606(19)
_cell_angle_gamma                90
_cell_volume                     1698.27(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    6581
_cell_measurement_theta_min      4.35
_cell_measurement_theta_max      69.29

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.562
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8379
_exptl_absorpt_correction_T_max  0.9369
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4368
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.956
_diffrn_reflns_theta_max         69.279
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             2996
_reflns_number_gt                2931
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.902
_reflns_Friedel_fraction_full    0.924

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

_computing_data_collection       'Apex2 (2014.9-1) (Bruker, 2014)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.4204P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1233 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2996
_refine_ls_number_parameters     297
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.88223(11) 0.5106(3) 0.54787(10) 0.0255(4) Uani 1 1 d . . . . .
H1 H 0.9380(13) 0.437(4) 0.5713(11) 0.021(5) Uiso 1 1 d . . . . .
O1 O 0.88625(7) 0.7507(3) 0.57540(7) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.92784(11) 0.7543(4) 0.65604(10) 0.0261(4) Uani 1 1 d . . . . .
H2A H 0.9866(14) 0.712(4) 0.6680(11) 0.024(5) Uiso 1 1 d . . . . .
H2B H 0.9244(13) 0.926(5) 0.6719(12) 0.025(5) Uiso 1 1 d . . . . .
C3 C 0.89045(10) 0.5850(3) 0.69635(10) 0.0234(4) Uani 1 1 d . . . . .
C4 C 0.90622(11) 0.6145(4) 0.77376(11) 0.0276(4) Uani 1 1 d . . . . .
H4 H 0.9379(15) 0.757(5) 0.7984(13) 0.036(6) Uiso 1 1 d . . . . .
C5 C 0.87671(12) 0.4529(4) 0.81303(10) 0.0304(4) Uani 1 1 d . . . . .
H5 H 0.8886(13) 0.471(4) 0.8681(12) 0.027(5) Uiso 1 1 d . . . . .
C6 C 0.82925(12) 0.2573(4) 0.77471(10) 0.0291(4) Uani 1 1 d . . . . .
H6 H 0.8071(13) 0.147(4) 0.8011(12) 0.022(5) Uiso 1 1 d . . . . .
C7 C 0.81161(11) 0.2306(4) 0.69734(10) 0.0259(4) Uani 1 1 d . . . . .
H7 H 0.7764(14) 0.089(4) 0.6699(12) 0.028(5) Uiso 1 1 d . . . . .
C8 C 0.84211(10) 0.3916(3) 0.65750(10) 0.0228(4) Uani 1 1 d . . . . .
C9 C 0.82173(11) 0.3586(3) 0.57255(10) 0.0234(4) Uani 1 1 d . . . . .
H9 H 0.8334(12) 0.188(4) 0.5630(11) 0.016(5) Uiso 1 1 d . . . . .
C10 C 0.86022(11) 0.5221(4) 0.46330(10) 0.0275(4) Uani 1 1 d . . . . .
H10 H 0.8238(15) 0.651(5) 0.4373(14) 0.039(6) Uiso 1 1 d . . . . .
C11 C 0.88890(11) 0.3643(4) 0.42653(10) 0.0267(4) Uani 1 1 d . . . . .
H11 H 0.9263(15) 0.233(5) 0.4574(13) 0.037(6) Uiso 1 1 d . . . . .
C12 C 0.87463(10) 0.3555(3) 0.34463(10) 0.0250(4) Uani 1 1 d . . . . .
C13 C 0.90741(12) 0.1629(4) 0.31792(11) 0.0292(4) Uani 1 1 d . . . . .
H13 H 0.9385(14) 0.037(5) 0.3536(13) 0.029(6) Uiso 1 1 d . . . . .
C14 C 0.89810(12) 0.1463(4) 0.24194(10) 0.0293(4) Uani 1 1 d . . . . .
H14 H 0.9216(15) 0.007(5) 0.2249(13) 0.035(6) Uiso 1 1 d . . . . .
C15 C 0.85606(11) 0.3248(4) 0.19110(10) 0.0283(4) Uani 1 1 d . . . . .
H15 H 0.8507(13) 0.312(4) 0.1394(13) 0.028(6) Uiso 1 1 d . . . . .
C16 C 0.82332(11) 0.5179(4) 0.21700(11) 0.0286(4) Uani 1 1 d . . . . .
H16 H 0.7918(14) 0.646(5) 0.1808(13) 0.031(6) Uiso 1 1 d . . . . .
C17 C 0.83217(11) 0.5329(4) 0.29272(11) 0.0272(4) Uani 1 1 d . . . . .
H17 H 0.8113(14) 0.658(5) 0.3089(13) 0.029(6) Uiso 1 1 d . . . . .
C18 C 0.73120(11) 0.4108(3) 0.52672(9) 0.0227(4) Uani 1 1 d . . . . .
C19 C 0.68483(11) 0.2462(4) 0.47256(10) 0.0275(4) Uani 1 1 d . . . . .
H19 H 0.7108(13) 0.098(4) 0.4659(12) 0.026(5) Uiso 1 1 d . . . . .
C20 C 0.60115(12) 0.2858(4) 0.43019(11) 0.0302(4) Uani 1 1 d . . . . .
H20 H 0.5703(15) 0.167(5) 0.3949(14) 0.038(6) Uiso 1 1 d . . . . .
C21 C 0.56319(11) 0.4930(4) 0.44119(10) 0.0282(4) Uani 1 1 d . . . . .
H21 H 0.5025(15) 0.524(4) 0.4107(13) 0.032(6) Uiso 1 1 d . . . . .
C22 C 0.60912(11) 0.6609(4) 0.49455(10) 0.0270(4) Uani 1 1 d . . . . .
H22 H 0.5856(13) 0.803(4) 0.5035(12) 0.024(5) Uiso 1 1 d . . . . .
C23 C 0.69226(11) 0.6195(4) 0.53706(10) 0.0249(4) Uani 1 1 d . . . . .
H23 H 0.7245(14) 0.737(5) 0.5746(13) 0.035(6) Uiso 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
C1 O1 1.427(2) . ?
C1 C10 1.501(2) . ?
C1 C9 1.549(2) . ?
C1 H1 0.99(2) . ?
O1 C2 1.425(2) . ?
C2 C3 1.502(3) . ?
C2 H2A 0.99(2) . ?
C2 H2B 1.01(3) . ?
C3 C4 1.395(3) . ?
C3 C8 1.396(2) . ?
C4 C5 1.380(3) . ?
C4 H4 0.98(3) . ?
C5 C6 1.396(3) . ?
C5 H5 0.99(2) . ?
C6 C7 1.386(2) . ?
C6 H6 0.96(2) . ?
C7 C8 1.395(3) . ?
C7 H7 1.01(2) . ?
C8 C9 1.522(2) . ?
C9 C18 1.517(2) . ?
C9 H9 1.00(2) . ?
C10 C11 1.326(3) . ?
C10 H10 0.96(3) . ?
C11 C12 1.475(2) . ?
C11 H11 1.01(3) . ?
C12 C13 1.393(3) . ?
C12 C17 1.395(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.99(2) . ?
C14 C15 1.388(3) . ?
C14 H14 0.98(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.95(2) . ?
C16 C17 1.384(3) . ?
C16 H16 1.00(2) . ?
C17 H17 0.89(3) . ?
C18 C19 1.388(3) . ?
C18 C23 1.394(3) . ?
C19 C20 1.394(3) . ?
C19 H19 0.97(2) . ?
C20 C21 1.382(3) . ?
C20 H20 0.95(3) . ?
C21 C22 1.390(3) . ?
C21 H21 1.01(2) . ?
C22 C23 1.389(3) . ?
C22 H22 0.93(2) . ?
C23 H23 0.98(3) . ?

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 C10 107.87(15) . . ?
O1 C1 C9 110.45(14) . . ?
C10 C1 C9 114.17(15) . . ?
O1 C1 H1 108.4(13) . . ?
C10 C1 H1 108.4(12) . . ?
C9 C1 H1 107.4(12) . . ?
C2 O1 C1 109.87(14) . . ?
O1 C2 C3 112.95(15) . . ?
O1 C2 H2A 108.3(12) . . ?
C3 C2 H2A 109.8(13) . . ?
O1 C2 H2B 105.6(12) . . ?
C3 C2 H2B 111.1(13) . . ?
H2A C2 H2B 109.1(18) . . ?
C4 C3 C8 119.32(17) . . ?
C4 C3 C2 120.22(16) . . ?
C8 C3 C2 120.42(16) . . ?
C5 C4 C3 121.24(18) . . ?
C5 C4 H4 121.9(14) . . ?
C3 C4 H4 116.9(15) . . ?
C4 C5 C6 119.69(17) . . ?
C4 C5 H5 121.6(14) . . ?
C6 C5 H5 118.7(14) . . ?
C7 C6 C5 119.28(18) . . ?
C7 C6 H6 120.4(13) . . ?
C5 C6 H6 120.2(13) . . ?
C6 C7 C8 121.32(18) . . ?
C6 C7 H7 118.6(13) . . ?
C8 C7 H7 120.1(13) . . ?
C7 C8 C3 119.13(16) . . ?
C7 C8 C9 120.33(16) . . ?
C3 C8 C9 120.54(16) . . ?
C18 C9 C8 111.56(14) . . ?
C18 C9 C1 113.53(15) . . ?
C8 C9 C1 109.40(14) . . ?
C18 C9 H9 108.4(11) . . ?
C8 C9 H9 108.7(11) . . ?
C1 C9 H9 104.9(11) . . ?
C11 C10 C1 122.15(17) . . ?
C11 C10 H10 122.0(15) . . ?
C1 C10 H10 115.8(15) . . ?
C10 C11 C12 128.43(17) . . ?
C10 C11 H11 117.7(14) . . ?
C12 C11 H11 113.9(14) . . ?
C13 C12 C17 118.09(16) . . ?
C13 C12 C11 118.21(17) . . ?
C17 C12 C11 123.67(17) . . ?
C14 C13 C12 121.26(18) . . ?
C14 C13 H13 119.0(14) . . ?
C12 C13 H13 119.7(14) . . ?
C13 C14 C15 119.95(18) . . ?
C13 C14 H14 119.1(13) . . ?
C15 C14 H14 120.9(13) . . ?
C16 C15 C14 119.37(17) . . ?
C16 C15 H15 121.5(14) . . ?
C14 C15 H15 119.1(14) . . ?
C17 C16 C15 120.51(18) . . ?
C17 C16 H16 119.2(14) . . ?
C15 C16 H16 120.2(14) . . ?
C16 C17 C12 120.81(18) . . ?
C16 C17 H17 119.9(15) . . ?
C12 C17 H17 119.3(15) . . ?
C19 C18 C23 118.28(16) . . ?
C19 C18 C9 119.44(17) . . ?
C23 C18 C9 122.27(16) . . ?
C18 C19 C20 121.14(19) . . ?
C18 C19 H19 119.1(12) . . ?
C20 C19 H19 119.7(12) . . ?
C21 C20 C19 120.00(18) . . ?
C21 C20 H20 120.5(15) . . ?
C19 C20 H20 119.5(15) . . ?
C20 C21 C22 119.49(17) . . ?
C20 C21 H21 120.6(14) . . ?
C22 C21 H21 119.9(14) . . ?
C23 C22 C21 120.25(18) . . ?
C23 C22 H22 117.9(13) . . ?
C21 C22 H22 121.9(13) . . ?
C22 C23 C18 120.82(17) . . ?
C22 C23 H23 120.3(14) . . ?
C18 C23 H23 118.9(14) . . ?

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
C10 C1 O1 C2 -164.53(13) . . . . ?
C9 C1 O1 C2 70.07(18) . . . . ?
C1 O1 C2 C3 -54.09(19) . . . . ?
O1 C2 C3 C4 -160.97(16) . . . . ?
O1 C2 C3 C8 21.4(2) . . . . ?
C8 C3 C4 C5 1.7(3) . . . . ?
C2 C3 C4 C5 -176.03(17) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C5 C6 C7 C8 1.7(3) . . . . ?
C6 C7 C8 C3 -0.8(3) . . . . ?
C6 C7 C8 C9 -179.87(16) . . . . ?
C4 C3 C8 C7 -0.8(2) . . . . ?
C2 C3 C8 C7 176.85(16) . . . . ?
C4 C3 C8 C9 178.21(16) . . . . ?
C2 C3 C8 C9 -4.1(2) . . . . ?
C7 C8 C9 C18 70.0(2) . . . . ?
C3 C8 C9 C18 -109.04(18) . . . . ?
C7 C8 C9 C1 -163.56(16) . . . . ?
C3 C8 C9 C1 17.4(2) . . . . ?
O1 C1 C9 C18 75.86(19) . . . . ?
C10 C1 C9 C18 -45.9(2) . . . . ?
O1 C1 C9 C8 -49.47(18) . . . . ?
C10 C1 C9 C8 -171.22(15) . . . . ?
O1 C1 C10 C11 146.39(18) . . . . ?
C9 C1 C10 C11 -90.4(2) . . . . ?
C1 C10 C11 C12 -178.39(17) . . . . ?
C10 C11 C12 C13 -176.18(19) . . . . ?
C10 C11 C12 C17 5.7(3) . . . . ?
C17 C12 C13 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 -178.39(17) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C12 0.5(3) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C11 C12 C17 C16 177.78(17) . . . . ?
C8 C9 C18 C19 -130.14(17) . . . . ?
C1 C9 C18 C19 105.7(2) . . . . ?
C8 C9 C18 C23 49.7(2) . . . . ?
C1 C9 C18 C23 -74.5(2) . . . . ?
C23 C18 C19 C20 -0.9(3) . . . . ?
C9 C18 C19 C20 178.94(17) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
C20 C21 C22 C23 -0.7(3) . . . . ?
C21 C22 C23 C18 0.5(3) . . . . ?
C19 C18 C23 C22 0.3(3) . . . . ?
C9 C18 C23 C22 -179.52(17) . . . . ?

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
_geom_hbond_publ_flag
C9 H9 O1 1.00(2) 2.58(2) 3.560(2) 165.3(15) 1_545 yes

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_JF2851CuFMI
_database_code_depnum_ccdc_archive 'CCDC 1920825'
loop_
_audit_author_name
_audit_author_address
'James Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.0262(4)
_cell_length_b                   10.7097(4)
_cell_length_c                   14.6781(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1418.90(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      5.11
_cell_measurement_theta_max      72.15

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.764
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.115
_exptl_absorpt_coefficient_mu    0.679
_shelx_estimated_absorpt_T_min   0.625
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7268
_exptl_absorpt_correction_T_max  0.8416
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7991
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.112
_diffrn_reflns_theta_max         72.141
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2743
_reflns_number_gt                2718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Apex2 (2014.9-1) (Bruker, 2014)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;

JF2851 Duo Cu

A colorless rod with approximate orthogonal dimensions 0.764 x 0.170 x
0.115mm3 was placed and optically centered on the Bruker Duo(1) APEXII CCD
system at --183°C(90K).  Indexing of the unit cell used a random set of
reflections collected from three series of 0.5° wide omega-scans, 10 seconds
per frame, and 30 frames per series that were well distributed in reciprocal
space. Data were collected [CuKa] with 0.5° wide scans, variable time per
frame dependent upon detector 2theta angle and varying phi and omega angles
such that nearly all unique reflections were collected at least once.  The
crystal to detector distance was 5.15cm, thus providing a complete sphere of
data to 2thetamax=144.23°.

Structural determination and Refinement:
 All crystallographic calculations were performed on an Intel Xeon E5-1620v2
 at 3.70GHz an eight core processor and 16GB of extended memory. Data
 collected were corrected for Lorentz and polarization effects with Saint(1)
 and absorption using Blessing?s method and merged as incorporated with the
 program Sadabs(2,3). The SHELXTL(4) program package was implemented to
 determine the probable space group and set up the initial files. System
 symmetry, systematic absences and intensity statistics indicated the non-
 centrosymmetric orthorhombic space group P212121 (no. 19). The structure was
 determined by direct methods with the non-hydrogen atoms being located
 directly for the molecule using the program XT(5).  The structure was refined
 with XL(6). The data collected were merged for least squares refinement to
 2743 unique data [R(int)=0.0192]. All non-hydrogen atoms were refined
 anisotropically. Hydrogen atoms were idealized initially and then allowed to
 refine freely throughout the final refinement stages. The final structure was
 refined to convergence with R(F)=2.63%, wR(F2)=6.97%, GOF=1.065 for all 2743
 unique reflections [R(F)=2.62, wR(F2)=6.96% for those 2718 data with Fo >
 4sigma(Fo)]. The final difference- Fourier map was featureless indicating
 that the structure is both correct and complete. An empirical correction for
 extinction was also attempted and found to be 0.0028(5).  The absolute
 structure parameters were determined to be: Flack(x)(7), 0.03(5);
 Hooft(y)(8), 0.01(4) and Parsons(z)(6), 0.02(5) indicating that the
 structure?s absolute configuration has been determined reliably.


References:

1.	Bruker (2013) APEXII (Version 2014.9-1) and (2016) SAINT (Version 8.37a).
Bruker AXS Inc., Madison, Wisconsin, USA.

2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995).
Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, ?Siemens Area Detector
Absorption Correction? Universität Göttingen: Göttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison,
Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, Universität Göttingen: Göttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2018). SHELXL2018/3. Universität Göttingen: Göttingen,
Germany.

7.	On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta Cryst., A39,
876-881.

8.	Hooft, R.W.W, Straver, L.H. & Spek, A.L. (2008). J. Appl, Cryst. 41, 96-
103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron


Acknowledgment:  We thank the National Science Foundation (Grant CHE-0840444)
for the Dual Source X-ray diffractometer.

J.C. Fettinger
;



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.2099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1128 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2743
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.43521(17) 0.47948(15) 0.25612(11) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.49138(14) 0.54330(11) 0.32789(9) 0.0178(3) Uani 1 1 d . . . . .
O1 O 0.33442(13) 0.40449(11) 0.26328(8) 0.0274(3) Uani 1 1 d . . . . .
C2 C 0.59063(18) 0.60580(15) 0.16047(11) 0.0232(3) Uani 1 1 d . . . . .
H2A H 0.531(2) 0.6821(18) 0.1619(13) 0.023(5) Uiso 1 1 d . . . . .
H2B H 0.638(2) 0.5951(19) 0.1011(14) 0.026(5) Uiso 1 1 d . . . . .
O2 O 0.49352(13) 0.49906(10) 0.17238(8) 0.0249(3) Uani 1 1 d . . . . .
C3 C 0.70347(18) 0.60774(14) 0.23592(10) 0.0198(3) Uani 1 1 d . . . . .
H3A H 0.774(2) 0.6792(19) 0.2276(13) 0.021(5) Uiso 1 1 d . . . . .
H3B H 0.761(2) 0.532(2) 0.2342(14) 0.025(5) Uiso 1 1 d . . . . .
C4 C 0.62387(16) 0.62327(12) 0.32605(10) 0.0166(3) Uani 1 1 d . . . . .
H4 H 0.592(2) 0.7100(18) 0.3317(12) 0.019(4) Uiso 1 1 d . . . . .
C5 C 0.72345(16) 0.59466(14) 0.40901(10) 0.0165(3) Uani 1 1 d . . . . .
H5 H 0.799(2) 0.6552(17) 0.4078(13) 0.017(4) Uiso 1 1 d . . . . .
C6 C 0.63385(17) 0.61228(13) 0.49519(10) 0.0179(3) Uani 1 1 d . . . . .
C7 C 0.70081(18) 0.65653(14) 0.57464(11) 0.0214(3) Uani 1 1 d . . . . .
H7 H 0.806(2) 0.676(2) 0.5735(14) 0.027(5) Uiso 1 1 d . . . . .
C8 C 0.6194(2) 0.67167(14) 0.65389(11) 0.0239(3) Uani 1 1 d . . . . .
H8 H 0.670(2) 0.703(2) 0.7090(15) 0.033(5) Uiso 1 1 d . . . . .
C9 C 0.46901(19) 0.64136(14) 0.65447(10) 0.0241(3) Uani 1 1 d . . . . .
H9 H 0.408(2) 0.6480(18) 0.7108(14) 0.021(4) Uiso 1 1 d . . . . .
C10 C 0.40155(17) 0.59961(14) 0.57546(11) 0.0215(3) Uani 1 1 d . . . . .
H10 H 0.299(2) 0.5790(18) 0.5772(13) 0.022(5) Uiso 1 1 d . . . . .
C11 C 0.48299(18) 0.58474(13) 0.49524(10) 0.0184(3) Uani 1 1 d . . . . .
C12 C 0.40480(16) 0.53424(14) 0.41243(11) 0.0201(3) Uani 1 1 d . . . . .
H12A H 0.382(2) 0.4474(18) 0.4216(12) 0.017(4) Uiso 1 1 d . . . . .
H12B H 0.311(2) 0.5766(18) 0.4046(13) 0.020(4) Uiso 1 1 d . . . . .
C13 C 0.79980(16) 0.46817(14) 0.40673(10) 0.0170(3) Uani 1 1 d . . . . .
C14 C 0.72271(17) 0.35605(14) 0.41644(10) 0.0185(3) Uani 1 1 d . . . . .
H14 H 0.622(2) 0.3563(17) 0.4279(13) 0.024(5) Uiso 1 1 d . . . . .
C15 C 0.79609(17) 0.24184(14) 0.41446(11) 0.0204(3) Uani 1 1 d . . . . .
H15 H 0.738(2) 0.163(2) 0.4191(14) 0.028(5) Uiso 1 1 d . . . . .
C16 C 0.94914(17) 0.23786(15) 0.40385(10) 0.0212(3) Uani 1 1 d . . . . .
H16 H 1.001(2) 0.1571(18) 0.4033(13) 0.024(5) Uiso 1 1 d . . . . .
C17 C 1.02786(17) 0.34852(16) 0.39551(10) 0.0215(3) Uani 1 1 d . . . . .
H17 H 1.134(2) 0.3471(18) 0.3906(13) 0.024(5) Uiso 1 1 d . . . . .
C18 C 0.95361(16) 0.46256(15) 0.39653(10) 0.0193(3) Uani 1 1 d . . . . .
H18 H 1.007(2) 0.5390(19) 0.3916(12) 0.024(5) Uiso 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
C1 O1 1.2180(19) . ?
C1 O2 1.3534(19) . ?
C1 N1 1.354(2) . ?
N1 C12 1.4697(19) . ?
N1 C4 1.4712(18) . ?
C2 O2 1.4511(19) . ?
C2 C3 1.505(2) . ?
C2 H2A 0.98(2) . ?
C2 H2B 0.98(2) . ?
C3 C4 1.515(2) . ?
C3 H3A 1.01(2) . ?
C3 H3B 0.97(2) . ?
C4 C5 1.544(2) . ?
C4 H4 0.976(19) . ?
C5 C6 1.513(2) . ?
C5 C13 1.520(2) . ?
C5 H5 0.939(19) . ?
C6 C11 1.393(2) . ?
C6 C7 1.396(2) . ?
C7 C8 1.385(2) . ?
C7 H7 0.97(2) . ?
C8 C9 1.396(3) . ?
C8 H8 0.99(2) . ?
C9 C10 1.384(2) . ?
C9 H9 1.00(2) . ?
C10 C11 1.397(2) . ?
C10 H10 0.96(2) . ?
C11 C12 1.506(2) . ?
C12 H12A 0.962(19) . ?
C12 H12B 0.97(2) . ?
C13 C14 1.395(2) . ?
C13 C18 1.398(2) . ?
C14 C15 1.391(2) . ?
C14 H14 0.93(2) . ?
C15 C16 1.391(2) . ?
C15 H15 1.00(2) . ?
C16 C17 1.387(2) . ?
C16 H16 0.98(2) . ?
C17 C18 1.393(2) . ?
C17 H17 0.96(2) . ?
C18 H18 0.95(2) . ?

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 O2 118.09(14) . . ?
O1 C1 N1 123.04(14) . . ?
O2 C1 N1 118.86(13) . . ?
C1 N1 C12 115.12(12) . . ?
C1 N1 C4 125.73(13) . . ?
C12 N1 C4 119.08(12) . . ?
O2 C2 C3 109.33(12) . . ?
O2 C2 H2A 108.9(11) . . ?
C3 C2 H2A 110.2(11) . . ?
O2 C2 H2B 106.3(12) . . ?
C3 C2 H2B 111.1(12) . . ?
H2A C2 H2B 111.0(16) . . ?
C1 O2 C2 117.80(12) . . ?
C2 C3 C4 108.86(13) . . ?
C2 C3 H3A 110.7(11) . . ?
C4 C3 H3A 108.9(11) . . ?
C2 C3 H3B 109.5(12) . . ?
C4 C3 H3B 111.7(12) . . ?
H3A C3 H3B 107.1(15) . . ?
N1 C4 C3 109.73(12) . . ?
N1 C4 C5 110.07(11) . . ?
C3 C4 C5 113.01(12) . . ?
N1 C4 H4 108.4(11) . . ?
C3 C4 H4 108.5(11) . . ?
C5 C4 H4 107.0(11) . . ?
C6 C5 C13 111.83(12) . . ?
C6 C5 C4 108.86(12) . . ?
C13 C5 C4 115.04(12) . . ?
C6 C5 H5 108.4(11) . . ?
C13 C5 H5 106.7(11) . . ?
C4 C5 H5 105.6(11) . . ?
C11 C6 C7 119.64(14) . . ?
C11 C6 C5 119.76(13) . . ?
C7 C6 C5 120.60(14) . . ?
C8 C7 C6 120.76(15) . . ?
C8 C7 H7 120.6(12) . . ?
C6 C7 H7 118.7(12) . . ?
C7 C8 C9 119.58(15) . . ?
C7 C8 H8 118.7(13) . . ?
C9 C8 H8 121.7(13) . . ?
C10 C9 C8 119.86(14) . . ?
C10 C9 H9 118.2(11) . . ?
C8 C9 H9 121.9(11) . . ?
C9 C10 C11 120.77(15) . . ?
C9 C10 H10 118.7(12) . . ?
C11 C10 H10 120.5(12) . . ?
C6 C11 C10 119.37(14) . . ?
C6 C11 C12 122.25(13) . . ?
C10 C11 C12 118.33(14) . . ?
N1 C12 C11 114.12(12) . . ?
N1 C12 H12A 107.1(11) . . ?
C11 C12 H12A 109.5(11) . . ?
N1 C12 H12B 109.5(11) . . ?
C11 C12 H12B 109.8(11) . . ?
H12A C12 H12B 106.6(16) . . ?
C14 C13 C18 118.00(14) . . ?
C14 C13 C5 122.59(12) . . ?
C18 C13 C5 119.40(14) . . ?
C15 C14 C13 121.14(13) . . ?
C15 C14 H14 118.3(12) . . ?
C13 C14 H14 120.4(12) . . ?
C16 C15 C14 120.14(14) . . ?
C16 C15 H15 120.3(12) . . ?
C14 C15 H15 119.5(12) . . ?
C17 C16 C15 119.51(15) . . ?
C17 C16 H16 120.3(12) . . ?
C15 C16 H16 120.2(12) . . ?
C16 C17 C18 120.10(13) . . ?
C16 C17 H17 120.3(12) . . ?
C18 C17 H17 119.6(12) . . ?
C17 C18 C13 121.11(14) . . ?
C17 C18 H18 120.6(12) . . ?
C13 C18 H18 118.3(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C12 -11.1(2) . . . . ?
O2 C1 N1 C12 169.20(12) . . . . ?
O1 C1 N1 C4 172.15(14) . . . . ?
O2 C1 N1 C4 -7.6(2) . . . . ?
O1 C1 O2 C2 167.33(14) . . . . ?
N1 C1 O2 C2 -12.9(2) . . . . ?
C3 C2 O2 C1 48.10(18) . . . . ?
O2 C2 C3 C4 -62.50(15) . . . . ?
C1 N1 C4 C3 -9.14(19) . . . . ?
C12 N1 C4 C3 174.18(12) . . . . ?
C1 N1 C4 C5 -134.12(14) . . . . ?
C12 N1 C4 C5 49.21(16) . . . . ?
C2 C3 C4 N1 42.77(15) . . . . ?
C2 C3 C4 C5 166.03(12) . . . . ?
N1 C4 C5 C6 -56.69(14) . . . . ?
C3 C4 C5 C6 -179.76(12) . . . . ?
N1 C4 C5 C13 69.70(15) . . . . ?
C3 C4 C5 C13 -53.37(16) . . . . ?
C13 C5 C6 C11 -94.97(15) . . . . ?
C4 C5 C6 C11 33.25(17) . . . . ?
C13 C5 C6 C7 85.36(16) . . . . ?
C4 C5 C6 C7 -146.42(13) . . . . ?
C11 C6 C7 C8 0.9(2) . . . . ?
C5 C6 C7 C8 -179.40(13) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C10 -1.7(2) . . . . ?
C8 C9 C10 C11 1.4(2) . . . . ?
C7 C6 C11 C10 -1.2(2) . . . . ?
C5 C6 C11 C10 179.10(13) . . . . ?
C7 C6 C11 C12 -178.71(14) . . . . ?
C5 C6 C11 C12 1.6(2) . . . . ?
C9 C10 C11 C6 0.1(2) . . . . ?
C9 C10 C11 C12 177.65(13) . . . . ?
C1 N1 C12 C11 168.95(12) . . . . ?
C4 N1 C12 C11 -14.03(18) . . . . ?
C6 C11 C12 N1 -13.0(2) . . . . ?
C10 C11 C12 N1 169.48(12) . . . . ?
C6 C5 C13 C14 55.33(18) . . . . ?
C4 C5 C13 C14 -69.53(18) . . . . ?
C6 C5 C13 C18 -123.24(15) . . . . ?
C4 C5 C13 C18 111.90(15) . . . . ?
C18 C13 C14 C15 -1.1(2) . . . . ?
C5 C13 C14 C15 -179.69(14) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C16 C17 C18 C13 0.6(2) . . . . ?
C14 C13 C18 C17 0.4(2) . . . . ?
C5 C13 C18 C17 179.02(13) . . . . ?

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
_geom_hbond_publ_flag
C3 H3A O1 1.01(2) 2.61(2) 3.1964(19) 117.2(13) 3_655 yes
C4 H4 O1 0.976(19) 2.592(19) 3.3063(18) 130.2(14) 3_655 yes

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_JF2831FMI
_database_code_depnum_ccdc_archive 'CCDC 1921674'
loop_
_audit_author_name
_audit_author_address
'James Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.5431(2)
_cell_length_b                   17.2727(6)
_cell_length_c                   17.7127(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1695.89(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9462
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      72.09

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    0.675
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8744
_exptl_absorpt_correction_T_max  0.9370
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10237
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.574
_diffrn_reflns_theta_max         72.081
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3335
_reflns_number_gt                3267
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Apex3 (2017.3) (Bruker, 2017)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.3293P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0042(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1342 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.08(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3335
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7252(3) 0.44513(9) 0.12222(8) 0.0143(3) Uani 1 1 d . . . . .
H1 H 0.804(3) 0.4697(10) 0.0760(10) 0.008(4) Uiso 1 1 d . . . . .
O1 O 0.4745(2) 0.46443(6) 0.12087(6) 0.0154(2) Uani 1 1 d . . . . .
C2 C 0.8445(3) 0.48384(9) 0.19197(9) 0.0136(3) Uani 1 1 d . . . . .
H2 H 1.009(4) 0.4745(11) 0.1857(11) 0.012(4) Uiso 1 1 d . . . . .
C3 C 0.7938(3) 0.57032(8) 0.18826(8) 0.0139(3) Uani 1 1 d . . . . .
C4 C 0.5973(3) 0.59820(9) 0.14748(8) 0.0142(3) Uani 1 1 d . . . . .
C5 C 0.4419(3) 0.54412(9) 0.10133(9) 0.0160(3) Uani 1 1 d . . . . .
H5A H 0.269(4) 0.5576(11) 0.1094(11) 0.019(5) Uiso 1 1 d . . . . .
H5B H 0.481(4) 0.5509(10) 0.0470(10) 0.010(4) Uiso 1 1 d . . . . .
C6 C 0.5462(3) 0.67739(9) 0.14714(9) 0.0159(3) Uani 1 1 d . . . . .
H6 H 0.414(4) 0.6963(11) 0.1190(11) 0.018(5) Uiso 1 1 d . . . . .
C7 C 0.6926(3) 0.72839(9) 0.18625(9) 0.0161(3) Uani 1 1 d . . . . .
H7 H 0.657(4) 0.7828(12) 0.1860(11) 0.016(5) Uiso 1 1 d . . . . .
C8 C 0.8923(3) 0.70120(9) 0.22602(9) 0.0164(3) Uani 1 1 d . . . . .
H8 H 0.993(4) 0.7368(11) 0.2522(11) 0.019(5) Uiso 1 1 d . . . . .
C9 C 0.9410(3) 0.62245(9) 0.22708(8) 0.0154(3) Uani 1 1 d . . . . .
H9 H 1.074(4) 0.6042(11) 0.2544(12) 0.019(5) Uiso 1 1 d . . . . .
C10 C 0.7526(3) 0.35823(8) 0.11718(8) 0.0144(3) Uani 1 1 d . . . . .
C11 C 0.5795(3) 0.30786(9) 0.14698(9) 0.0161(3) Uani 1 1 d . . . . .
H11 H 0.439(4) 0.3285(11) 0.1728(11) 0.017(5) Uiso 1 1 d . . . . .
C12 C 0.6061(3) 0.22835(9) 0.14017(9) 0.0166(3) Uani 1 1 d . . . . .
H12 H 0.488(4) 0.1936(12) 0.1625(12) 0.019(5) Uiso 1 1 d . . . . .
C13 C 0.8056(3) 0.19753(9) 0.10330(8) 0.0142(3) Uani 1 1 d . . . . .
O13 O 0.8166(2) 0.11828(6) 0.10054(6) 0.0173(2) Uani 1 1 d . . . . .
C14 C 0.9804(3) 0.24677(9) 0.07291(8) 0.0160(3) Uani 1 1 d . . . . .
H14 H 1.118(4) 0.2268(12) 0.0466(11) 0.020(5) Uiso 1 1 d . . . . .
C15 C 0.9510(3) 0.32671(9) 0.08031(9) 0.0161(3) Uani 1 1 d . . . . .
H15 H 1.069(5) 0.3604(13) 0.0592(12) 0.029(6) Uiso 1 1 d . . . . .
C16 C 1.0348(3) 0.08528(9) 0.07188(10) 0.0201(3) Uani 1 1 d . . . . .
H16A H 1.177(4) 0.1047(13) 0.0984(13) 0.027(6) Uiso 1 1 d . . . . .
H16B H 1.048(4) 0.0975(12) 0.0182(12) 0.025(5) Uiso 1 1 d . . . . .
H16C H 1.024(4) 0.0290(13) 0.0825(12) 0.026(5) Uiso 1 1 d . . . . .
C17 C 0.7634(3) 0.44941(8) 0.26673(8) 0.0137(3) Uani 1 1 d . . . . .
C18 C 0.5549(3) 0.47496(9) 0.30336(9) 0.0170(3) Uani 1 1 d . . . . .
H18 H 0.455(4) 0.5171(12) 0.2822(12) 0.021(5) Uiso 1 1 d . . . . .
C19 C 0.4844(3) 0.44277(9) 0.37167(9) 0.0173(3) Uani 1 1 d . . . . .
H19 H 0.340(4) 0.4604(12) 0.3959(12) 0.025(5) Uiso 1 1 d . . . . .
C20 C 0.6217(3) 0.38377(9) 0.40418(9) 0.0155(3) Uani 1 1 d . . . . .
C21 C 0.8327(3) 0.35795(9) 0.36914(9) 0.0161(3) Uani 1 1 d . . . . .
H21 H 0.930(4) 0.3162(12) 0.3922(12) 0.021(5) Uiso 1 1 d . . . . .
C22 C 0.9006(3) 0.39135(9) 0.30085(9) 0.0148(3) Uani 1 1 d . . . . .
H22 H 1.047(4) 0.3748(11) 0.2763(11) 0.018(5) Uiso 1 1 d . . . . .
C23 C 0.5379(3) 0.34795(9) 0.47341(9) 0.0182(3) Uani 1 1 d . . . . .
N23 N 0.4648(3) 0.31932(9) 0.52717(8) 0.0250(3) 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
C1 O1 1.4294(18) . ?
C1 C10 1.5113(19) . ?
C1 C2 1.553(2) . ?
C1 H1 1.021(19) . ?
O1 C5 1.4307(17) . ?
C2 C17 1.520(2) . ?
C2 C3 1.521(2) . ?
C2 H2 0.93(2) . ?
C3 C4 1.393(2) . ?
C3 C9 1.396(2) . ?
C4 C6 1.397(2) . ?
C4 C5 1.511(2) . ?
C5 H5A 1.00(2) . ?
C5 H5B 0.992(19) . ?
C6 C7 1.384(2) . ?
C6 H6 0.95(2) . ?
C7 C8 1.393(2) . ?
C7 H7 0.96(2) . ?
C8 C9 1.387(2) . ?
C8 H8 0.95(2) . ?
C9 H9 0.94(2) . ?
C10 C15 1.390(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.387(2) . ?
C11 H11 0.97(2) . ?
C12 C13 1.391(2) . ?
C12 H12 0.97(2) . ?
C13 O13 1.3711(18) . ?
C13 C14 1.397(2) . ?
O13 C16 1.430(2) . ?
C14 C15 1.396(2) . ?
C14 H14 0.96(2) . ?
C15 H15 0.95(2) . ?
C16 H16A 0.98(2) . ?
C16 H16B 0.98(2) . ?
C16 H16C 0.99(2) . ?
C17 C22 1.396(2) . ?
C17 C18 1.397(2) . ?
C18 C19 1.388(2) . ?
C18 H18 0.99(2) . ?
C19 C20 1.396(2) . ?
C19 H19 0.96(2) . ?
C20 C21 1.397(2) . ?
C20 C23 1.450(2) . ?
C21 C22 1.392(2) . ?
C21 H21 0.99(2) . ?
C22 H22 0.96(2) . ?
C23 N23 1.147(2) . ?

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 C10 109.16(12) . . ?
O1 C1 C2 109.10(12) . . ?
C10 C1 C2 115.59(12) . . ?
O1 C1 H1 107.9(10) . . ?
C10 C1 H1 108.8(10) . . ?
C2 C1 H1 106.0(10) . . ?
C1 O1 C5 110.55(11) . . ?
C17 C2 C3 111.54(12) . . ?
C17 C2 C1 113.49(12) . . ?
C3 C2 C1 108.04(12) . . ?
C17 C2 H2 108.9(12) . . ?
C3 C2 H2 110.2(12) . . ?
C1 C2 H2 104.3(12) . . ?
C4 C3 C9 119.30(14) . . ?
C4 C3 C2 120.42(14) . . ?
C9 C3 C2 120.27(14) . . ?
C3 C4 C6 119.96(14) . . ?
C3 C4 C5 120.84(13) . . ?
C6 C4 C5 119.17(14) . . ?
O1 C5 C4 113.08(12) . . ?
O1 C5 H5A 108.1(11) . . ?
C4 C5 H5A 109.1(12) . . ?
O1 C5 H5B 108.7(10) . . ?
C4 C5 H5B 109.2(11) . . ?
H5A C5 H5B 108.6(16) . . ?
C7 C6 C4 120.15(15) . . ?
C7 C6 H6 119.9(12) . . ?
C4 C6 H6 119.9(12) . . ?
C6 C7 C8 120.29(14) . . ?
C6 C7 H7 120.0(12) . . ?
C8 C7 H7 119.7(12) . . ?
C9 C8 C7 119.48(15) . . ?
C9 C8 H8 120.8(12) . . ?
C7 C8 H8 119.7(12) . . ?
C8 C9 C3 120.80(15) . . ?
C8 C9 H9 119.4(12) . . ?
C3 C9 H9 119.8(12) . . ?
C15 C10 C11 118.45(14) . . ?
C15 C10 C1 119.74(14) . . ?
C11 C10 C1 121.78(14) . . ?
C12 C11 C10 120.69(15) . . ?
C12 C11 H11 119.3(11) . . ?
C10 C11 H11 120.0(11) . . ?
C11 C12 C13 120.30(15) . . ?
C11 C12 H12 120.4(12) . . ?
C13 C12 H12 119.3(12) . . ?
O13 C13 C12 115.73(14) . . ?
O13 C13 C14 124.30(14) . . ?
C12 C13 C14 119.97(14) . . ?
C13 O13 C16 116.61(12) . . ?
C15 C14 C13 119.02(14) . . ?
C15 C14 H14 119.7(12) . . ?
C13 C14 H14 121.3(12) . . ?
C10 C15 C14 121.56(14) . . ?
C10 C15 H15 119.2(14) . . ?
C14 C15 H15 119.2(14) . . ?
O13 C16 H16A 112.0(13) . . ?
O13 C16 H16B 108.8(13) . . ?
H16A C16 H16B 109.5(19) . . ?
O13 C16 H16C 105.8(14) . . ?
H16A C16 H16C 107.2(19) . . ?
H16B C16 H16C 113.6(17) . . ?
C22 C17 C18 118.45(14) . . ?
C22 C17 C2 119.80(14) . . ?
C18 C17 C2 121.74(13) . . ?
C19 C18 C17 120.76(14) . . ?
C19 C18 H18 118.0(13) . . ?
C17 C18 H18 121.2(13) . . ?
C18 C19 C20 119.92(15) . . ?
C18 C19 H19 119.9(13) . . ?
C20 C19 H19 120.2(13) . . ?
C19 C20 C21 120.39(14) . . ?
C19 C20 C23 119.08(15) . . ?
C21 C20 C23 120.50(14) . . ?
C22 C21 C20 118.69(14) . . ?
C22 C21 H21 120.9(13) . . ?
C20 C21 H21 120.4(12) . . ?
C21 C22 C17 121.78(15) . . ?
C21 C22 H22 119.8(12) . . ?
C17 C22 H22 118.4(12) . . ?
N23 C23 C20 177.88(19) . . ?

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
C10 C1 O1 C5 -161.47(11) . . . . ?
C2 C1 O1 C5 71.35(14) . . . . ?
O1 C1 C2 C17 68.87(15) . . . . ?
C10 C1 C2 C17 -54.56(18) . . . . ?
O1 C1 C2 C3 -55.36(15) . . . . ?
C10 C1 C2 C3 -178.80(13) . . . . ?
C17 C2 C3 C4 -102.21(16) . . . . ?
C1 C2 C3 C4 23.18(19) . . . . ?
C17 C2 C3 C9 76.41(18) . . . . ?
C1 C2 C3 C9 -158.19(13) . . . . ?
C9 C3 C4 C6 -1.4(2) . . . . ?
C2 C3 C4 C6 177.20(14) . . . . ?
C9 C3 C4 C5 176.65(13) . . . . ?
C2 C3 C4 C5 -4.7(2) . . . . ?
C1 O1 C5 C4 -49.74(16) . . . . ?
C3 C4 C5 O1 16.4(2) . . . . ?
C6 C4 C5 O1 -165.47(13) . . . . ?
C3 C4 C6 C7 1.0(2) . . . . ?
C5 C4 C6 C7 -177.09(14) . . . . ?
C4 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C9 -1.0(2) . . . . ?
C7 C8 C9 C3 0.6(2) . . . . ?
C4 C3 C9 C8 0.6(2) . . . . ?
C2 C3 C9 C8 -178.01(14) . . . . ?
O1 C1 C10 C15 147.26(14) . . . . ?
C2 C1 C10 C15 -89.34(17) . . . . ?
O1 C1 C10 C11 -30.97(19) . . . . ?
C2 C1 C10 C11 92.43(18) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
C1 C10 C11 C12 178.57(14) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 O13 179.14(14) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C13 O13 C16 -171.99(13) . . . . ?
C14 C13 O13 C16 7.1(2) . . . . ?
O13 C13 C14 C15 -179.00(14) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C1 C10 C15 C14 -178.54(14) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?
C3 C2 C17 C22 -142.70(14) . . . . ?
C1 C2 C17 C22 94.98(16) . . . . ?
C3 C2 C17 C18 36.5(2) . . . . ?
C1 C2 C17 C18 -85.85(17) . . . . ?
C22 C17 C18 C19 -0.7(2) . . . . ?
C2 C17 C18 C19 -179.89(14) . . . . ?
C17 C18 C19 C20 -0.5(2) . . . . ?
C18 C19 C20 C21 1.4(2) . . . . ?
C18 C19 C20 C23 -176.62(15) . . . . ?
C19 C20 C21 C22 -1.0(2) . . . . ?
C23 C20 C21 C22 176.93(15) . . . . ?
C20 C21 C22 C17 -0.2(2) . . . . ?
C18 C17 C22 C21 1.1(2) . . . . ?
C2 C17 C22 C21 -179.75(14) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031

