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

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

data_new555
_database_code_depnum_ccdc_archive 'CCDC 1849340'
_audit_update_record             
;
2018-06-14 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 3-(tert-butyl)-2H-naphtho[1,8-bc]furan-2-one
;
_chemical_name_common            ?
_chemical_melting_point          379-382
_chemical_formula_moiety         'C15 H14 O2'
_chemical_formula_sum            'C15 H14 O2'
_chemical_formula_weight         226.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   14.0730(6)
_cell_length_b                   6.8273(4)
_cell_length_c                   12.0491(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1157.68(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1254
_cell_measurement_theta_min      3.6710
_cell_measurement_theta_max      28.5760


_exptl_crystal_description       Block
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.495
_exptl_crystal_size_min          0.137
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            4309
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.895
_diffrn_reflns_theta_max         29.090
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1484
_reflns_number_gt                1268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+0.3937P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1484
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
O2 O 0.04084(11) 0.7500 0.70880(13) 0.0323(4) Uani 1 2 d S T P . .
O5 O 0.19283(12) 0.7500 0.76373(14) 0.0452(5) Uani 1 2 d S T P . .
C1 C -0.00638(15) 0.7500 0.60765(18) 0.0248(5) Uani 1 2 d S T P . .
C2 C -0.10177(16) 0.7500 0.5882(2) 0.0311(5) Uani 1 2 d S T P . .
H2 H -0.1471 0.7500 0.6466 0.037 Uiso 1 2 calc R U P . .
C3 C -0.12877(15) 0.7500 0.4743(2) 0.0339(6) Uani 1 2 d S T P . .
H3 H -0.1947 0.7500 0.4572 0.041 Uiso 1 2 calc R U P . .
C4 C -0.06603(16) 0.7500 0.3886(2) 0.0318(6) Uani 1 2 d S T P . .
H4 H -0.0885 0.7500 0.3142 0.038 Uiso 1 2 calc R U P . .
C5 C 0.03354(15) 0.7500 0.41022(19) 0.0244(5) Uani 1 2 d S T P . .
C6 C 0.11204(17) 0.7500 0.33688(18) 0.0284(5) Uani 1 2 d S T P . .
H6 H 0.1014 0.7500 0.2590 0.034 Uiso 1 2 calc R U P . .
C7 C 0.20356(16) 0.7500 0.37679(18) 0.0273(5) Uani 1 2 d S T P . .
H7 H 0.2538 0.7500 0.3241 0.033 Uiso 1 2 calc R U P . .
C8 C 0.22871(14) 0.7500 0.49133(18) 0.0209(4) Uani 1 2 d S T P . .
C9 C 0.15194(14) 0.7500 0.56411(17) 0.0213(4) Uani 1 2 d S T P . .
C10 C 0.05919(13) 0.7500 0.52153(18) 0.0209(4) Uani 1 2 d S T P . .
C11 C 0.13877(15) 0.7500 0.68685(18) 0.0277(5) Uani 1 2 d S T P . .
C12 C 0.33347(14) 0.7500 0.52825(19) 0.0257(5) Uani 1 2 d S T P . .
C13 C 0.40240(17) 0.7500 0.4308(2) 0.0407(6) Uani 1 2 d S T P . .
H13A H 0.3920 0.8677 0.3856 0.061 Uiso 1 1 d . U . . .
H13B H 0.4677 0.7500 0.4584 0.061 Uiso 1 2 d S U P . .
C14 C 0.35274(11) 0.9345(2) 0.59757(16) 0.0349(4) Uani 1 1 d . . . . .
H14A H 0.4179 0.9305 0.6261 0.052 Uiso 1 1 calc R U . . .
H14B H 0.3080 0.9398 0.6598 0.052 Uiso 1 1 calc R U . . .
H14C H 0.3446 1.0510 0.5510 0.052 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
O2 C1 1.388(3) . ?
O2 C11 1.403(3) . ?
O5 C11 1.199(3) . ?
C1 C2 1.363(3) . ?
C1 C10 1.389(3) . ?
C2 C3 1.424(4) . ?
C3 C4 1.359(4) . ?
C4 C5 1.425(3) . ?
C5 C10 1.389(3) . ?
C5 C6 1.415(3) . ?
C6 C7 1.375(3) . ?
C7 C8 1.425(3) . ?
C8 C9 1.391(3) . ?
C8 C12 1.540(3) . ?
C9 C10 1.402(3) . ?
C9 C11 1.490(3) . ?
C12 C13 1.523(3) . ?
C12 C14 1.536(2) . ?
C12 C14 1.536(2) 8_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C11 107.74(16) . . ?
C2 C1 O2 128.5(2) . . ?
C2 C1 C10 121.8(2) . . ?
O2 C1 C10 109.75(18) . . ?
C1 C2 C3 115.4(2) . . ?
C4 C3 C2 124.0(2) . . ?
C3 C4 C5 120.0(2) . . ?
C10 C5 C6 113.59(19) . . ?
C10 C5 C4 115.6(2) . . ?
C6 C5 C4 130.8(2) . . ?
C7 C6 C5 120.9(2) . . ?
C6 C7 C8 124.9(2) . . ?
C9 C8 C7 114.68(18) . . ?
C9 C8 C12 124.14(19) . . ?
C7 C8 C12 121.18(18) . . ?
C8 C9 C10 119.48(19) . . ?
C8 C9 C11 136.21(19) . . ?
C10 C9 C11 104.31(17) . . ?
C1 C10 C5 123.28(19) . . ?
C1 C10 C9 110.19(19) . . ?
C5 C10 C9 126.5(2) . . ?
O5 C11 O2 118.5(2) . . ?
O5 C11 C9 133.5(2) . . ?
O2 C11 C9 108.01(17) . . ?
C13 C12 C14 107.86(12) . . ?
C13 C12 C14 107.86(12) . 8_575 ?
C14 C12 C14 110.2(2) . 8_575 ?
C13 C12 C8 112.78(19) . . ?
C14 C12 C8 109.04(11) . . ?
C14 C12 C8 109.04(11) 8_575 . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_JB025
_database_code_depnum_ccdc_archive 'CCDC 1849341'
_audit_update_record             
;
2018-06-14 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_vrf_PLAT027_JB025               
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......    20.00 Degree
RESPONSE: this was the only one crystal which we were able to grow of this
substance.  The NMR of the full amount of material is consistent with 
this lactol structure.
;
_vrf_PLAT230_JB025               
;
PROBLEM: Hirshfeld Test Diff for C11 --C12A
RESPONSE: There are two conformations of the t-butyl group in ratio
82:18.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        
;
 3-(tert-butyl)-2-methyl-2H-naphtho[1,8-bc]furan-2-ol
;
_chemical_name_common            ?
_chemical_melting_point          381-383
_chemical_formula_moiety         'C16 H18 O2'
_chemical_formula_sum            'C16 H18 O2'
_chemical_formula_weight         242.30

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4248(5)
_cell_length_b                   22.9673(7)
_cell_length_c                   9.8566(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.446(5)
_cell_angle_gamma                90
_cell_volume                     2599.63(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2904
_cell_measurement_theta_min      3.8280
_cell_measurement_theta_max      28.6540

_exptl_crystal_description       Block
_exptl_crystal_colour            Pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.173
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            7739
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.854
_diffrn_reflns_theta_max         29.033
_diffrn_reflns_theta_full        20.000
_diffrn_measured_fraction_theta_max 0.769
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.769
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.769
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             5334
_reflns_number_gt                4107
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.9590P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5334
_refine_ls_number_parameters     372
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.052
_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
O1 O -0.02274(12) 0.43205(6) 0.63779(16) 0.0297(3) Uani 1 1 d . . . . .
O2 O -0.00160(13) 0.43010(7) 0.88237(16) 0.0292(4) Uani 1 1 d . . . . .
O3 O -0.33499(12) 0.51864(6) 0.95137(15) 0.0267(3) Uani 1 1 d . . . . .
O4 O -0.16724(12) 0.50657(6) 0.90686(16) 0.0254(3) Uani 1 1 d . . . . .
C1 C -0.12728(17) 0.42806(9) 0.5212(2) 0.0239(4) Uani 1 1 d . . . . .
C2 C -0.15962(19) 0.45436(9) 0.3872(2) 0.0299(5) Uani 1 1 d . . . . .
H2 H -0.107911 0.478929 0.363246 0.036 Uiso 1 1 calc R U . . .
C3 C -0.27387(19) 0.44314(9) 0.2859(2) 0.0307(5) Uani 1 1 d . . . . .
H3 H -0.297538 0.459538 0.190464 0.037 Uiso 1 1 calc R U . . .
C4 C -0.35222(18) 0.40984(9) 0.3185(2) 0.0279(5) Uani 1 1 d . . . . .
H4 H -0.428565 0.404146 0.247099 0.033 Uiso 1 1 calc R U . . .
C5 C -0.31899(17) 0.38377(8) 0.4595(2) 0.0225(4) Uani 1 1 d . . . . .
C6 C -0.38602(18) 0.35019(9) 0.5179(2) 0.0268(5) Uani 1 1 d . . . . .
H6 H -0.465333 0.342181 0.459624 0.032 Uiso 1 1 calc R U . . .
C7 C -0.33738(18) 0.32904(9) 0.6580(2) 0.0258(5) Uani 1 1 d . . . . .
H7 H -0.386240 0.307064 0.693067 0.031 Uiso 1 1 calc R U . . .
C8 C -0.21873(18) 0.33730(8) 0.7566(2) 0.0229(4) Uani 1 1 d . . . . .
C9 C -0.15162(16) 0.37042(8) 0.7002(2) 0.0201(4) Uani 1 1 d . . . . .
C10 C -0.20360(16) 0.39249(8) 0.5571(2) 0.0199(4) Uani 1 1 d . . . . .
C11 C -0.18166(14) 0.31125(6) 0.91215(17) 0.0298(5) Uani 1 1 d D . . . .
C12 C -0.2524(2) 0.25657(9) 0.9111(3) 0.0504(9) Uani 0.819 1 d D . P A 1
H12A H -0.245648 0.228745 0.839349 0.076 Uiso 0.819 1 calc R U P A 1
H12B H -0.334330 0.267142 0.884309 0.076 Uiso 0.819 1 calc R U P A 1
H12C H -0.222407 0.238814 1.008894 0.076 Uiso 0.819 1 calc R U P A 1
C12A C -0.2847(6) 0.2980(5) 0.9560(11) 0.074(5) Uani 0.181 1 d D . P A 2
H12D H -0.256249 0.279881 1.053382 0.111 Uiso 0.181 1 calc R U P A 2
H12E H -0.338421 0.271319 0.884226 0.111 Uiso 0.181 1 calc R U P A 2
H12F H -0.325443 0.334269 0.958421 0.111 Uiso 0.181 1 calc R U P A 2
C13 C -0.05229(15) 0.29557(11) 0.9810(3) 0.0386(7) Uani 0.819 1 d D . P A 1
H13A H -0.035977 0.275373 1.074308 0.058 Uiso 0.819 1 calc R U P A 1
H13B H -0.005531 0.331195 0.998494 0.058 Uiso 0.819 1 calc R U P A 1
H13C H -0.032514 0.270081 0.914132 0.058 Uiso 0.819 1 calc R U P A 1
H2A H -0.059(2) 0.4511(12) 0.872(3) 0.053(9) Uiso 1 1 d . . . . .
H4A H -0.121(3) 0.5298(13) 0.981(4) 0.069(9) Uiso 1 1 d . . . . .
C13A C -0.1247(8) 0.2535(2) 0.8996(11) 0.050(4) Uani 0.181 1 d D . P A 2
H13D H -0.060114 0.261011 0.868035 0.075 Uiso 0.181 1 calc R U P A 2
H13E H -0.182401 0.228520 0.827381 0.075 Uiso 0.181 1 calc R U P A 2
H13F H -0.095038 0.234020 0.995275 0.075 Uiso 0.181 1 calc R U P A 2
C14 C -0.2064(2) 0.35674(9) 1.0103(3) 0.0349(6) Uani 0.819 1 d D . P A 1
H14A H -0.187639 0.340408 1.108509 0.052 Uiso 0.819 1 calc R U P A 1
H14B H -0.288938 0.367544 0.967916 0.052 Uiso 0.819 1 calc R U P A 1
H14C H -0.158485 0.391348 1.017099 0.052 Uiso 0.819 1 calc R U P A 1
C14A C -0.0928(6) 0.3471(3) 1.0347(8) 0.044(4) Uani 0.181 1 d D . P A 2
H14D H -0.121887 0.386933 1.032048 0.067 Uiso 0.181 1 calc R U P A 2
H14E H -0.018799 0.348013 1.020738 0.067 Uiso 0.181 1 calc R U P A 2
H14F H -0.080607 0.329410 1.129904 0.067 Uiso 0.181 1 calc R U P A 2
C15 C -0.02547(17) 0.39469(8) 0.7588(2) 0.0226(4) Uani 1 1 d . . . . .
C16 C 0.07551(18) 0.35331(10) 0.7865(2) 0.0313(5) Uani 1 1 d . . . . .
H16A H 0.145144 0.375489 0.794810 0.047 Uiso 1 1 calc R U . . .
H16B H 0.056414 0.325762 0.704684 0.047 Uiso 1 1 calc R U . . .
H16C H 0.090370 0.331890 0.877847 0.047 Uiso 1 1 calc R U . . .
C17 C -0.37120(16) 0.57066(9) 0.9849(2) 0.0240(4) Uani 1 1 d . . . . .
C18 C -0.42863(18) 0.58056(10) 1.0763(2) 0.0310(5) Uani 1 1 d . . . . .
H18 H -0.446795 0.549862 1.128551 0.037 Uiso 1 1 calc R U . . .
C19 C -0.45967(19) 0.63900(11) 1.0890(2) 0.0364(6) Uani 1 1 d . . . . .
H19 H -0.498817 0.647265 1.152826 0.044 Uiso 1 1 calc R U . . .
C20 C -0.43622(19) 0.68425(10) 1.0140(3) 0.0352(5) Uani 1 1 d . . . . .
H20 H -0.460078 0.722617 1.025397 0.042 Uiso 1 1 calc R U . . .
C21 C -0.37646(18) 0.67385(9) 0.9195(2) 0.0282(5) Uani 1 1 d . . . . .
C22 C -0.34452(19) 0.71301(9) 0.8315(3) 0.0334(5) Uani 1 1 d . . . . .
H22 H -0.362824 0.753166 0.831657 0.040 Uiso 1 1 calc R U . . .
C23 C -0.28723(19) 0.69377(9) 0.7454(2) 0.0311(5) Uani 1 1 d . . . . .
H23 H -0.266190 0.722061 0.689630 0.037 Uiso 1 1 calc R U . . .
C24 C -0.25663(17) 0.63453(9) 0.7329(2) 0.0249(4) Uani 1 1 d . . . . .
C25 C -0.28786(16) 0.59520(8) 0.8193(2) 0.0210(4) Uani 1 1 d . . . . .
C26 C -0.34461(16) 0.61593(9) 0.9086(2) 0.0227(4) Uani 1 1 d . . . . .
C27 C -0.20163(19) 0.62072(10) 0.6206(2) 0.0310(5) Uani 1 1 d . . . . .
C28 C -0.1337(2) 0.67332(11) 0.5962(3) 0.0450(6) Uani 1 1 d . . . . .
H28A H -0.076881 0.686632 0.690957 0.067 Uiso 1 1 calc R U . . .
H28B H -0.188148 0.704978 0.549488 0.067 Uiso 1 1 calc R U . . .
H28C H -0.092968 0.661742 0.532727 0.067 Uiso 1 1 calc R U . . .
C29 C -0.3002(2) 0.60643(11) 0.4736(2) 0.0387(6) Uani 1 1 d . . . . .
H29A H -0.267230 0.597932 0.399962 0.058 Uiso 1 1 calc R U . . .
H29B H -0.353047 0.639813 0.441370 0.058 Uiso 1 1 calc R U . . .
H29C H -0.343389 0.572407 0.485580 0.058 Uiso 1 1 calc R U . . .
C30 C -0.1153(2) 0.57017(10) 0.6671(3) 0.0363(5) Uani 1 1 d . . . . .
H30A H -0.053616 0.578978 0.762413 0.054 Uiso 1 1 calc R U . . .
H30B H -0.080863 0.564534 0.593669 0.054 Uiso 1 1 calc R U . . .
H30C H -0.155957 0.534584 0.675156 0.054 Uiso 1 1 calc R U . . .
C31 C -0.28036(17) 0.52826(8) 0.8430(2) 0.0222(4) Uani 1 1 d . . . . .
C32 C -0.35015(18) 0.49162(9) 0.7121(2) 0.0277(5) Uani 1 1 d . . . . .
H32A H -0.315702 0.494146 0.637900 0.042 Uiso 1 1 calc R U . . .
H32B H -0.430539 0.505884 0.670454 0.042 Uiso 1 1 calc R U . . .
H32C H -0.349595 0.451006 0.742820 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 C1 1.370(2) . ?
O1 C15 1.480(2) . ?
O2 C15 1.399(2) . ?
O2 H2A 0.83(3) . ?
O3 C17 1.361(2) . ?
O3 C31 1.485(2) . ?
O4 C31 1.394(2) . ?
O4 H4A 0.91(3) . ?
C1 C2 1.366(3) . ?
C1 C10 1.396(3) . ?
C2 C3 1.413(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.422(3) . ?
C4 H4 0.9500 . ?
C5 C10 1.403(3) . ?
C5 C6 1.409(3) . ?
C6 C7 1.368(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.435(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C8 C11 1.544(2) . ?
C9 C10 1.403(3) . ?
C9 C15 1.552(3) . ?
C11 C14A 1.5296(10) . ?
C11 C12A 1.5300(10) . ?
C11 C13 1.5300(10) . ?
C11 C13A 1.5305(10) . ?
C11 C12 1.5303(10) . ?
C11 C14 1.5324(10) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C15 C16 1.513(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.365(3) . ?
C17 C26 1.395(3) . ?
C18 C19 1.415(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.369(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.415(3) . ?
C20 H20 0.9500 . ?
C21 C26 1.404(3) . ?
C21 C22 1.408(3) . ?
C22 C23 1.372(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.431(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.395(3) . ?
C24 C27 1.539(3) . ?
C25 C26 1.404(3) . ?
C25 C31 1.552(3) . ?
C27 C30 1.528(3) . ?
C27 C29 1.534(3) . ?
C27 C28 1.544(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.506(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
C1 O1 C15 109.33(14) . . ?
C15 O2 H2A 110(2) . . ?
C17 O3 C31 109.17(14) . . ?
C31 O4 H4A 111.7(19) . . ?
C2 C1 O1 128.04(18) . . ?
C2 C1 C10 121.76(19) . . ?
O1 C1 C10 110.18(17) . . ?
C1 C2 C3 116.59(19) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C4 C3 C2 123.3(2) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C3 C4 C5 119.82(19) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C10 C5 C6 114.02(18) . . ?
C10 C5 C4 116.69(17) . . ?
C6 C5 C4 129.28(19) . . ?
C7 C6 C5 120.30(19) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 125.44(18) . . ?
C6 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C9 C8 C7 114.81(18) . . ?
C9 C8 C11 127.70(17) . . ?
C7 C8 C11 117.43(16) . . ?
C8 C9 C10 118.88(17) . . ?
C8 C9 C15 136.20(18) . . ?
C10 C9 C15 104.83(16) . . ?
C1 C10 C9 111.71(17) . . ?
C1 C10 C5 121.69(18) . . ?
C9 C10 C5 126.54(18) . . ?
C14A C11 C12A 108.30(10) . . ?
C14A C11 C13A 108.29(10) . . ?
C12A C11 C13A 108.25(10) . . ?
C13 C11 C12 108.24(9) . . ?
C13 C11 C14 108.11(9) . . ?
C12 C11 C14 108.11(9) . . ?
C14A C11 C8 115.3(4) . . ?
C12A C11 C8 113.2(4) . . ?
C13 C11 C8 113.33(15) . . ?
C13A C11 C8 103.1(4) . . ?
C12 C11 C8 111.01(16) . . ?
C14 C11 C8 107.89(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12A H12D 109.5 . . ?
C11 C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C11 C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C13A H13D 109.5 . . ?
C11 C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
C11 C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C14A H14D 109.5 . . ?
C11 C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
C11 C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
O2 C15 O1 107.57(15) . . ?
O2 C15 C16 108.81(17) . . ?
O1 C15 C16 103.71(15) . . ?
O2 C15 C9 112.38(15) . . ?
O1 C15 C9 103.84(15) . . ?
C16 C15 C9 119.44(16) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C18 127.66(19) . . ?
O3 C17 C26 110.79(16) . . ?
C18 C17 C26 121.5(2) . . ?
C17 C18 C19 116.4(2) . . ?
C17 C18 H18 121.8 . . ?
C19 C18 H18 121.8 . . ?
C20 C19 C18 123.4(2) . . ?
C20 C19 H19 118.3 . . ?
C18 C19 H19 118.3 . . ?
C19 C20 C21 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C26 C21 C22 113.82(19) . . ?
C26 C21 C20 116.4(2) . . ?
C22 C21 C20 129.8(2) . . ?
C23 C22 C21 120.68(19) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 125.3(2) . . ?
C22 C23 H23 117.4 . . ?
C24 C23 H23 117.4 . . ?
C25 C24 C23 114.71(18) . . ?
C25 C24 C27 127.54(18) . . ?
C23 C24 C27 117.62(18) . . ?
C24 C25 C26 119.13(18) . . ?
C24 C25 C31 135.91(17) . . ?
C26 C25 C31 104.92(16) . . ?
C17 C26 C21 122.21(19) . . ?
C17 C26 C25 111.36(17) . . ?
C21 C26 C25 126.39(19) . . ?
C30 C27 C29 109.69(19) . . ?
C30 C27 C24 113.24(17) . . ?
C29 C27 C24 108.03(17) . . ?
C30 C27 C28 106.16(18) . . ?
C29 C27 C28 107.89(18) . . ?
C24 C27 C28 111.70(18) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O4 C31 O3 106.29(15) . . ?
O4 C31 C32 109.79(16) . . ?
O3 C31 C32 105.14(15) . . ?
O4 C31 C25 114.45(16) . . ?
O3 C31 C25 103.74(15) . . ?
C32 C31 C25 116.29(16) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 O1 C1 C2 -178.2(2) . . . . ?
C15 O1 C1 C10 2.8(2) . . . . ?
O1 C1 C2 C3 -179.59(19) . . . . ?
C10 C1 C2 C3 -0.7(3) . . . . ?
C1 C2 C3 C4 2.6(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C10 -2.2(3) . . . . ?
C3 C4 C5 C6 177.2(2) . . . . ?
C10 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C7 -179.7(2) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C11 178.35(18) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C11 C8 C9 C10 -176.99(16) . . . . ?
C7 C8 C9 C15 176.17(19) . . . . ?
C11 C8 C9 C15 -1.1(3) . . . . ?
C2 C1 C10 C9 -179.88(19) . . . . ?
O1 C1 C10 C9 -0.9(2) . . . . ?
C2 C1 C10 C5 -2.6(3) . . . . ?
O1 C1 C10 C5 176.40(16) . . . . ?
C8 C9 C10 C1 175.68(17) . . . . ?
C15 C9 C10 C1 -1.4(2) . . . . ?
C8 C9 C10 C5 -1.4(3) . . . . ?
C15 C9 C10 C5 -178.46(18) . . . . ?
C6 C5 C10 C1 -175.47(18) . . . . ?
C4 C5 C10 C1 4.1(3) . . . . ?
C6 C5 C10 C9 1.4(3) . . . . ?
C4 C5 C10 C9 -179.13(18) . . . . ?
C9 C8 C11 C14A 32.6(4) . . . . ?
C7 C8 C11 C14A -144.6(4) . . . . ?
C9 C8 C11 C12A 158.0(5) . . . . ?
C7 C8 C11 C12A -19.2(5) . . . . ?
C9 C8 C11 C13 -30.7(2) . . . . ?
C7 C8 C11 C13 152.12(16) . . . . ?
C9 C8 C11 C13A -85.2(4) . . . . ?
C7 C8 C11 C13A 97.5(4) . . . . ?
C9 C8 C11 C12 -152.73(19) . . . . ?
C7 C8 C11 C12 30.1(2) . . . . ?
C9 C8 C11 C14 89.0(2) . . . . ?
C7 C8 C11 C14 -88.22(18) . . . . ?
C1 O1 C15 O2 -122.79(17) . . . . ?
C1 O1 C15 C16 122.03(17) . . . . ?
C1 O1 C15 C9 -3.50(19) . . . . ?
C8 C9 C15 O2 -57.4(3) . . . . ?
C10 C9 C15 O2 118.84(17) . . . . ?
C8 C9 C15 O1 -173.4(2) . . . . ?
C10 C9 C15 O1 2.88(18) . . . . ?
C8 C9 C15 C16 71.8(3) . . . . ?
C10 C9 C15 C16 -111.91(19) . . . . ?
C31 O3 C17 C18 177.8(2) . . . . ?
C31 O3 C17 C26 -0.6(2) . . . . ?
O3 C17 C18 C19 -178.15(19) . . . . ?
C26 C17 C18 C19 0.1(3) . . . . ?
C17 C18 C19 C20 0.8(3) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C20 C21 C26 0.2(3) . . . . ?
C19 C20 C21 C22 179.2(2) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
C20 C21 C22 C23 -179.3(2) . . . . ?
C21 C22 C23 C24 1.3(3) . . . . ?
C22 C23 C24 C25 -1.1(3) . . . . ?
C22 C23 C24 C27 174.9(2) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C27 C24 C25 C26 -175.65(19) . . . . ?
C23 C24 C25 C31 177.2(2) . . . . ?
C27 C24 C25 C31 1.6(4) . . . . ?
O3 C17 C26 C21 177.65(18) . . . . ?
C18 C17 C26 C21 -0.9(3) . . . . ?
O3 C17 C26 C25 -0.2(2) . . . . ?
C18 C17 C26 C25 -178.71(19) . . . . ?
C22 C21 C26 C17 -178.48(19) . . . . ?
C20 C21 C26 C17 0.7(3) . . . . ?
C22 C21 C26 C25 -1.0(3) . . . . ?
C20 C21 C26 C25 178.21(19) . . . . ?
C24 C25 C26 C17 178.85(17) . . . . ?
C31 C25 C26 C17 0.8(2) . . . . ?
C24 C25 C26 C21 1.1(3) . . . . ?
C31 C25 C26 C21 -176.90(19) . . . . ?
C25 C24 C27 C30 -36.1(3) . . . . ?
C23 C24 C27 C30 148.4(2) . . . . ?
C25 C24 C27 C29 85.6(3) . . . . ?
C23 C24 C27 C29 -89.9(2) . . . . ?
C25 C24 C27 C28 -155.9(2) . . . . ?
C23 C24 C27 C28 28.6(3) . . . . ?
C17 O3 C31 O4 122.07(16) . . . . ?
C17 O3 C31 C32 -121.54(17) . . . . ?
C17 O3 C31 C25 1.04(19) . . . . ?
C24 C25 C31 O4 66.0(3) . . . . ?
C26 C25 C31 O4 -116.48(18) . . . . ?
C24 C25 C31 O3 -178.6(2) . . . . ?
C26 C25 C31 O3 -1.11(19) . . . . ?
C24 C25 C31 C32 -63.7(3) . . . . ?
C26 C25 C31 C32 113.77(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O4 0.84(3) 1.97(3) 2.785(2) 164(3) .
O4 H4A O2 0.90(3) 1.86(3) 2.740(2) 165(3) 3_567
O2 H2A O4 0.84(3) 1.97(3) 2.785(2) 164(3) .
O4 H4A O2 0.90(3) 1.86(3) 2.740(2) 165(3) 3_567


_refine_diff_density_max         0.267
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.044

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_JB014P
_database_code_depnum_ccdc_archive 'CCDC 1849343'
_audit_update_record             
;
2018-06-14 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_vrf_PLAT077_JB014P              
;
PROBLEM: Unitcell contains non-integer number of atoms ..     Please Check
RESPONSE: The final model contains 10% of a water molecule.
;

_vrf_PLAT309_JB014P              
;
PROBLEM: Single Bonded Oxygen (C-O > 1.3 Ang) ...........      O3 Check  
RESPONSE: This is the anionic oxygen of a naphthoate salt.
There are two independent such anions, with C-O bond lengths of
1.299(2) and 1.306(2) Ang.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
Tetramethylguanidinium 8-benzoylnaphth-1-oate 
;
_chemical_name_common            ?
_chemical_melting_point          373-376
_chemical_formula_moiety         'C22 H25.10 N3 O2.05'
_chemical_formula_sum            'C22 H25.10 N3 O2.05'
_chemical_formula_weight         364.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.2578(4)
_cell_length_b                   10.5748(5)
_cell_length_c                   23.1819(12)
_cell_angle_alpha                99.596(4)
_cell_angle_beta                 91.720(4)
_cell_angle_gamma                104.122(4)
_cell_volume                     1930.40(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4770
_cell_measurement_theta_min      3.4260
_cell_measurement_theta_max      29.4100

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             778
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.092
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            20316
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.825
_diffrn_reflns_theta_max         29.496
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_measurement_method       'ω scans'
_reflns_number_total             9106
_reflns_number_gt                6926
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
With the cation and anion modelled, there was still one peak in the
difference fourier to account for. This has been modelled as a 10% 
occupancy by water. There is indeed space for it, and it is involved 
in one hydrogen bond. It thus seems a plausible explanation.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+0.5982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9106
_refine_ls_number_parameters     515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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
O1 O 0.98121(15) 0.38244(11) 0.06724(5) 0.0201(3) Uani 1 1 d . . . . .
O2 O 0.59365(16) 0.32186(12) 0.04373(6) 0.0267(3) Uani 1 1 d . . . . .
O3 O 0.45301(16) 0.83449(12) 0.42969(5) 0.0227(3) Uani 1 1 d . . . . .
O4 O 0.09167(17) 0.88662(13) 0.41126(7) 0.0339(3) Uani 1 1 d . . . . .
N1 N 1.1317(2) 0.64274(16) 0.04801(7) 0.0208(3) Uani 1 1 d . . . . .
N2 N 1.27300(19) 0.86540(14) 0.06951(7) 0.0225(3) Uani 1 1 d . . . . .
N3 N 1.3139(2) 0.72137(14) 0.13054(7) 0.0246(4) Uani 1 1 d . . . . .
N4 N 0.4342(2) 0.09310(16) 0.45195(7) 0.0234(4) Uani 1 1 d . . . . .
N5 N 0.3594(2) 0.11329(16) 0.35718(7) 0.0268(4) Uani 1 1 d . . . . .
N6 N 0.3266(2) 0.26745(15) 0.43693(7) 0.0290(4) Uani 1 1 d . . . . .
H1A H 1.104(3) 0.646(2) 0.0102(11) 0.037(6) Uiso 1 1 d . . . . .
H1B H 1.095(2) 0.570(2) 0.0596(9) 0.027(6) Uiso 1 1 d . . . . .
H4A H 0.439(3) 0.003(2) 0.4393(10) 0.040(6) Uiso 1 1 d . . . . .
H4B H 0.467(3) 0.135(2) 0.4915(11) 0.045(7) Uiso 1 1 d . . . . .
C1 C 0.9928(2) 0.30352(16) 0.10368(8) 0.0186(4) Uani 1 1 d . . . . .
C2 C 1.1288(2) 0.24827(17) 0.10932(9) 0.0243(4) Uani 1 1 d . . . . .
H2 H 1.2188 0.2672 0.0849 0.029 Uiso 1 1 calc R U . . .
C3 C 1.1349(2) 0.16562(18) 0.15025(9) 0.0276(5) Uani 1 1 d . . . . .
H3 H 1.2288 0.1292 0.1526 0.033 Uiso 1 1 calc R U . . .
C4 C 1.0106(2) 0.13566(17) 0.18689(9) 0.0269(4) Uani 1 1 d . . . . .
H4 H 1.0190 0.0798 0.2144 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8695(2) 0.18787(17) 0.18390(8) 0.0226(4) Uani 1 1 d . . . . .
C6 C 0.7376(3) 0.16272(18) 0.22132(9) 0.0285(5) Uani 1 1 d . . . . .
H6 H 0.7434 0.1085 0.2498 0.034 Uiso 1 1 calc R U . . .
C7 C 0.6029(3) 0.21418(19) 0.21757(9) 0.0310(5) Uani 1 1 d . . . . .
H7 H 0.5185 0.1993 0.2444 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5885(2) 0.28939(18) 0.17397(9) 0.0270(4) Uani 1 1 d . . . . .
H8 H 0.4921 0.3222 0.1705 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7125(2) 0.31572(16) 0.13646(8) 0.0203(4) Uani 1 1 d . . . . .
C10 C 0.8587(2) 0.26937(16) 0.14136(8) 0.0191(4) Uani 1 1 d . . . . .
C11 C 0.6794(2) 0.38617(17) 0.08768(8) 0.0213(4) Uani 1 1 d . . . . .
C12 C 0.7317(2) 0.53372(17) 0.09777(8) 0.0211(4) Uani 1 1 d . . . . .
C13 C 0.6941(2) 0.59817(18) 0.05338(9) 0.0241(4) Uani 1 1 d . . . . .
H13 H 0.6410 0.5479 0.0169 0.029 Uiso 1 1 calc R U . . .
C14 C 0.7335(3) 0.73435(19) 0.06207(9) 0.0299(5) Uani 1 1 d . . . . .
H14 H 0.7064 0.7779 0.0318 0.036 Uiso 1 1 calc R U . . .
C15 C 0.8123(3) 0.80799(19) 0.11475(10) 0.0346(5) Uani 1 1 d . . . . .
H15 H 0.8390 0.9021 0.1207 0.041 Uiso 1 1 calc R U . . .
C16 C 0.8524(3) 0.74513(19) 0.15882(10) 0.0342(5) Uani 1 1 d . . . . .
H16 H 0.9074 0.7961 0.1949 0.041 Uiso 1 1 calc R U . . .
C17 C 0.8126(2) 0.60773(18) 0.15063(9) 0.0259(4) Uani 1 1 d . . . . .
H17 H 0.8403 0.5645 0.1809 0.031 Uiso 1 1 calc R U . . .
C18 C 1.2377(2) 0.74114(17) 0.08188(8) 0.0203(4) Uani 1 1 d . . . . .
C19 C 1.1720(3) 0.89592(18) 0.02352(9) 0.0277(4) Uani 1 1 d . . . . .
H19A H 1.2167 0.8739 -0.0145 0.042 Uiso 1 1 calc R U . . .
H19B H 1.1756 0.9906 0.0315 0.042 Uiso 1 1 calc R U . . .
H19C H 1.0560 0.8438 0.0227 0.042 Uiso 1 1 calc R U . . .
C20 C 1.4453(2) 0.94693(18) 0.07672(9) 0.0299(5) Uani 1 1 d . . . . .
H20A H 1.5087 0.9196 0.1067 0.045 Uiso 1 1 calc R U . . .
H20B H 1.4455 1.0403 0.0889 0.045 Uiso 1 1 calc R U . . .
H20C H 1.4974 0.9356 0.0394 0.045 Uiso 1 1 calc R U . . .
C21 C 1.3183(3) 0.58832(18) 0.13780(9) 0.0294(5) Uani 1 1 d . . . . .
H21A H 1.2179 0.5481 0.1562 0.044 Uiso 1 1 calc R U . . .
H21B H 1.4182 0.5927 0.1628 0.044 Uiso 1 1 calc R U . . .
H21C H 1.3220 0.5345 0.0993 0.044 Uiso 1 1 calc R U . . .
C22 C 1.3522(3) 0.8202(2) 0.18434(9) 0.0382(5) Uani 1 1 d . . . . .
H22A H 1.3132 0.8980 0.1786 0.057 Uiso 1 1 calc R U . . .
H22B H 1.4735 0.8467 0.1941 0.057 Uiso 1 1 calc R U . . .
H22C H 1.2958 0.7824 0.2165 0.057 Uiso 1 1 calc R U . . .
C23 C 0.4553(2) 0.74662(17) 0.38308(8) 0.0228(4) Uani 1 1 d . . . . .
C24 C 0.5998(3) 0.7303(2) 0.35742(9) 0.0355(5) Uani 1 1 d . . . . .
H24 H 0.7050 0.7860 0.3738 0.043 Uiso 1 1 calc R U . . .
C25 C 0.5940(3) 0.6326(2) 0.30739(10) 0.0436(6) Uani 1 1 d . . . . .
H25 H 0.6956 0.6248 0.2907 0.052 Uiso 1 1 calc R U . . .
C26 C 0.4470(3) 0.5491(2) 0.28237(9) 0.0390(6) Uani 1 1 d . . . . .
H26 H 0.4472 0.4819 0.2496 0.047 Uiso 1 1 calc R U . . .
C27 C 0.2955(3) 0.56248(18) 0.30503(8) 0.0292(5) Uani 1 1 d . . . . .
C28 C 0.1382(3) 0.48127(19) 0.27959(9) 0.0356(5) Uani 1 1 d . . . . .
H28 H 0.1347 0.4130 0.2469 0.043 Uiso 1 1 calc R U . . .
C29 C -0.0070(3) 0.4989(2) 0.30092(10) 0.0378(5) Uani 1 1 d . . . . .
H29 H -0.1108 0.4432 0.2832 0.045 Uiso 1 1 calc R U . . .
C30 C -0.0050(3) 0.5994(2) 0.34924(9) 0.0328(5) Uani 1 1 d . . . . .
H30 H -0.1075 0.6120 0.3636 0.039 Uiso 1 1 calc R U . . .
C31 C 0.1444(2) 0.67957(17) 0.37585(8) 0.0237(4) Uani 1 1 d . . . . .
C32 C 0.2974(2) 0.66208(17) 0.35518(8) 0.0218(4) Uani 1 1 d . . . . .
C33 C 0.1325(2) 0.79074(18) 0.42439(9) 0.0235(4) Uani 1 1 d . . . . .
C34 C 0.1473(2) 0.77489(17) 0.48679(9) 0.0235(4) Uani 1 1 d . . . . .
C35 C 0.1323(2) 0.87760(19) 0.53093(9) 0.0289(5) Uani 1 1 d . . . . .
H35 H 0.1160 0.9574 0.5210 0.035 Uiso 1 1 calc R U . . .
C36 C 0.1409(3) 0.8638(2) 0.58896(10) 0.0372(5) Uani 1 1 d . . . . .
H36 H 0.1304 0.9341 0.6189 0.045 Uiso 1 1 calc R U . . .
C37 C 0.1647(3) 0.7485(2) 0.60365(10) 0.0427(6) Uani 1 1 d . . . . .
H37 H 0.1705 0.7391 0.6437 0.051 Uiso 1 1 calc R U . . .
C38 C 0.1803(3) 0.6456(2) 0.56005(10) 0.0390(5) Uani 1 1 d . . . . .
H38 H 0.1965 0.5660 0.5702 0.047 Uiso 1 1 calc R U . . .
C39 C 0.1721(3) 0.65952(18) 0.50192(9) 0.0280(4) Uani 1 1 d . . . . .
H39 H 0.1835 0.5894 0.4721 0.034 Uiso 1 1 calc R U . . .
C40 C 0.3738(2) 0.15656(18) 0.41617(8) 0.0236(4) Uani 1 1 d . . . . .
C41 C 0.3429(3) 0.3760(2) 0.40429(11) 0.0417(6) Uani 1 1 d . . . . .
H41A H 0.3965 0.3554 0.3680 0.063 Uiso 1 1 calc R U . . .
H41B H 0.4116 0.4579 0.4282 0.063 Uiso 1 1 calc R U . . .
H41C H 0.2317 0.3877 0.3947 0.063 Uiso 1 1 calc R U . . .
C42 C 0.2974(3) 0.2987(2) 0.49863(9) 0.0335(5) Uani 1 1 d . . . . .
H42A H 0.2535 0.2163 0.5134 0.050 Uiso 1 1 calc R U . . .
H42B H 0.2161 0.3527 0.5031 0.050 Uiso 1 1 calc R U . . .
H42C H 0.4030 0.3480 0.5209 0.050 Uiso 1 1 calc R U . . .
C43 C 0.2132(3) 0.1189(2) 0.32170(10) 0.0406(6) Uani 1 1 d . . . . .
H43A H 0.1410 0.0292 0.3093 0.061 Uiso 1 1 calc R U . . .
H43B H 0.2496 0.1567 0.2870 0.061 Uiso 1 1 calc R U . . .
H43C H 0.1508 0.1745 0.3449 0.061 Uiso 1 1 calc R U . . .
C44 C 0.4352(3) 0.00830(19) 0.33214(9) 0.0314(5) Uani 1 1 d . . . . .
H44A H 0.5380 0.0143 0.3558 0.047 Uiso 1 1 calc R U . . .
H44B H 0.4621 0.0176 0.2919 0.047 Uiso 1 1 calc R U . . .
H44C H 0.3567 -0.0779 0.3318 0.047 Uiso 1 1 calc R U . . .
O5 O -0.069(2) -0.1140(16) 0.2989(7) 0.048(4) Uiso 0.1 1 d . . P . .
H5A H -0.0702 -0.1114 0.3359 0.060 Uiso 0.1 1 d . U P . .
H5B H -0.0239 -0.1812 0.2874 0.060 Uiso 0.1 1 d . U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.299(2) . ?
O2 C11 1.222(2) . ?
O3 C23 1.306(2) . ?
O4 C33 1.224(2) . ?
N1 C18 1.307(2) . ?
N1 H1A 0.91(2) . ?
N1 H1B 0.85(2) . ?
N2 C18 1.356(2) . ?
N2 C19 1.459(2) . ?
N2 C20 1.461(2) . ?
N3 C18 1.346(2) . ?
N3 C21 1.454(2) . ?
N3 C22 1.459(2) . ?
N4 C40 1.309(2) . ?
N4 H4A 0.96(2) . ?
N4 H4B 0.95(2) . ?
N5 C40 1.360(2) . ?
N5 C44 1.452(2) . ?
N5 C43 1.459(3) . ?
N6 C40 1.343(2) . ?
N6 C42 1.454(3) . ?
N6 C41 1.459(3) . ?
C1 C2 1.399(3) . ?
C1 C10 1.445(3) . ?
C2 C3 1.401(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.363(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.415(3) . ?
C5 C10 1.428(3) . ?
C6 C7 1.359(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.370(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.417(3) . ?
C9 C11 1.507(3) . ?
C11 C12 1.490(2) . ?
C12 C17 1.391(3) . ?
C12 C13 1.392(3) . ?
C13 C14 1.375(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.385(3) . ?
C23 C32 1.451(3) . ?
C24 C25 1.410(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.362(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.401(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.419(3) . ?
C27 C32 1.430(3) . ?
C28 C29 1.353(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.406(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.375(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.407(3) . ?
C31 C33 1.510(3) . ?
C33 C34 1.489(3) . ?
C34 C39 1.383(3) . ?
C34 C35 1.395(3) . ?
C35 C36 1.379(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.377(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.389(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.381(3) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
O5 H5A 0.853(17) . ?
O5 H5B 0.890(16) . ?

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
C18 N1 H1A 121.6(13) . . ?
C18 N1 H1B 120.5(14) . . ?
H1A N1 H1B 117.6(19) . . ?
C18 N2 C19 119.77(15) . . ?
C18 N2 C20 120.26(16) . . ?
C19 N2 C20 112.89(15) . . ?
C18 N3 C21 120.43(15) . . ?
C18 N3 C22 122.53(16) . . ?
C21 N3 C22 114.80(16) . . ?
C40 N4 H4A 120.6(13) . . ?
C40 N4 H4B 119.3(13) . . ?
H4A N4 H4B 120.0(19) . . ?
C40 N5 C44 120.16(16) . . ?
C40 N5 C43 120.46(17) . . ?
C44 N5 C43 113.13(17) . . ?
C40 N6 C42 120.24(16) . . ?
C40 N6 C41 122.21(18) . . ?
C42 N6 C41 115.78(17) . . ?
O1 C1 C2 124.14(17) . . ?
O1 C1 C10 119.11(16) . . ?
C2 C1 C10 116.75(17) . . ?
C1 C2 C3 121.28(18) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 122.22(18) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 119.82(18) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 122.70(18) . . ?
C4 C5 C10 118.82(17) . . ?
C6 C5 C10 118.48(17) . . ?
C7 C6 C5 121.59(19) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 119.94(19) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.55(19) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.75(18) . . ?
C8 C9 C11 116.80(17) . . ?
C10 C9 C11 122.28(16) . . ?
C9 C10 C5 118.54(17) . . ?
C9 C10 C1 120.41(16) . . ?
C5 C10 C1 121.05(16) . . ?
O2 C11 C12 121.64(17) . . ?
O2 C11 C9 118.86(16) . . ?
C12 C11 C9 118.95(15) . . ?
C17 C12 C13 119.69(17) . . ?
C17 C12 C11 121.73(17) . . ?
C13 C12 C11 118.55(16) . . ?
C14 C13 C12 120.24(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.12(19) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.14(18) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.22(19) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 119.56(19) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
N1 C18 N3 120.43(17) . . ?
N1 C18 N2 121.34(17) . . ?
N3 C18 N2 118.22(16) . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 C24 124.08(18) . . ?
O3 C23 C32 118.69(17) . . ?
C24 C23 C32 117.22(17) . . ?
C23 C24 C25 121.3(2) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 121.9(2) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 119.87(19) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 122.37(19) . . ?
C26 C27 C32 119.43(19) . . ?
C28 C27 C32 118.20(19) . . ?
C29 C28 C27 121.41(19) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 120.3(2) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 120.5(2) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 120.49(18) . . ?
C30 C31 C33 116.17(18) . . ?
C32 C31 C33 123.20(16) . . ?
C31 C32 C27 119.12(18) . . ?
C31 C32 C23 120.65(16) . . ?
C27 C32 C23 120.20(18) . . ?
O4 C33 C34 120.81(17) . . ?
O4 C33 C31 118.57(18) . . ?
C34 C33 C31 120.10(16) . . ?
C39 C34 C35 119.27(19) . . ?
C39 C34 C33 121.49(17) . . ?
C35 C34 C33 119.22(17) . . ?
C36 C35 C34 120.3(2) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C37 C36 C35 120.08(19) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 120.1(2) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C39 C38 C37 119.8(2) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 C34 120.40(19) . . ?
C38 C39 H39 119.8 . . ?
C34 C39 H39 119.8 . . ?
N4 C40 N6 120.59(18) . . ?
N4 C40 N5 121.00(18) . . ?
N6 C40 N5 118.40(17) . . ?
N6 C41 H41A 109.5 . . ?
N6 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N6 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N6 C42 H42A 109.5 . . ?
N6 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
N6 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N5 C43 H43A 109.5 . . ?
N5 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
N5 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N5 C44 H44A 109.5 . . ?
N5 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
N5 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
H5A O5 H5B 102.3(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.87(16) . . . . ?
C10 C1 C2 C3 -1.0(2) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -178.81(17) . . . . ?
C3 C4 C5 C10 1.3(3) . . . . ?
C4 C5 C6 C7 -179.99(17) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 3.0(3) . . . . ?
C6 C7 C8 C9 -2.5(3) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C7 C8 C9 C11 174.53(16) . . . . ?
C8 C9 C10 C5 3.7(2) . . . . ?
C11 C9 C10 C5 -171.44(15) . . . . ?
C8 C9 C10 C1 -176.69(16) . . . . ?
C11 C9 C10 C1 8.1(2) . . . . ?
C4 C5 C10 C9 176.69(15) . . . . ?
C6 C5 C10 C9 -3.2(2) . . . . ?
C4 C5 C10 C1 -2.9(2) . . . . ?
C6 C5 C10 C1 177.19(16) . . . . ?
O1 C1 C10 C9 3.3(2) . . . . ?
C2 C1 C10 C9 -176.86(15) . . . . ?
O1 C1 C10 C5 -177.15(15) . . . . ?
C2 C1 C10 C5 2.7(2) . . . . ?
C8 C9 C11 O2 -80.6(2) . . . . ?
C10 C9 C11 O2 94.7(2) . . . . ?
C8 C9 C11 C12 91.0(2) . . . . ?
C10 C9 C11 C12 -93.6(2) . . . . ?
O2 C11 C12 C17 172.43(18) . . . . ?
C9 C11 C12 C17 1.0(3) . . . . ?
O2 C11 C12 C13 -5.8(3) . . . . ?
C9 C11 C12 C13 -177.25(16) . . . . ?
C17 C12 C13 C14 -1.3(3) . . . . ?
C11 C12 C13 C14 176.99(17) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C13 C12 C17 C16 1.0(3) . . . . ?
C11 C12 C17 C16 -177.23(18) . . . . ?
C21 N3 C18 N1 17.6(3) . . . . ?
C22 N3 C18 N1 -144.48(19) . . . . ?
C21 N3 C18 N2 -162.92(16) . . . . ?
C22 N3 C18 N2 35.0(3) . . . . ?
C19 N2 C18 N1 10.4(3) . . . . ?
C20 N2 C18 N1 -138.09(18) . . . . ?
C19 N2 C18 N3 -169.10(16) . . . . ?
C20 N2 C18 N3 42.4(2) . . . . ?
O3 C23 C24 C25 179.38(19) . . . . ?
C32 C23 C24 C25 -2.0(3) . . . . ?
C23 C24 C25 C26 -0.7(4) . . . . ?
C24 C25 C26 C27 2.5(3) . . . . ?
C25 C26 C27 C28 177.8(2) . . . . ?
C25 C26 C27 C32 -1.5(3) . . . . ?
C26 C27 C28 C29 -177.7(2) . . . . ?
C32 C27 C28 C29 1.7(3) . . . . ?
C27 C28 C29 C30 0.1(3) . . . . ?
C28 C29 C30 C31 -0.9(3) . . . . ?
C29 C30 C31 C32 -0.1(3) . . . . ?
C29 C30 C31 C33 175.58(18) . . . . ?
C30 C31 C32 C27 1.9(3) . . . . ?
C33 C31 C32 C27 -173.50(17) . . . . ?
C30 C31 C32 C23 179.89(18) . . . . ?
C33 C31 C32 C23 4.5(3) . . . . ?
C26 C27 C32 C31 176.72(17) . . . . ?
C28 C27 C32 C31 -2.6(3) . . . . ?
C26 C27 C32 C23 -1.3(3) . . . . ?
C28 C27 C32 C23 179.37(17) . . . . ?
O3 C23 C32 C31 3.7(3) . . . . ?
C24 C23 C32 C31 -175.00(18) . . . . ?
O3 C23 C32 C27 -178.34(16) . . . . ?
C24 C23 C32 C27 3.0(3) . . . . ?
C30 C31 C33 O4 -73.4(2) . . . . ?
C32 C31 C33 O4 102.1(2) . . . . ?
C30 C31 C33 C34 98.4(2) . . . . ?
C32 C31 C33 C34 -86.1(2) . . . . ?
O4 C33 C34 C39 171.58(18) . . . . ?
C31 C33 C34 C39 0.0(3) . . . . ?
O4 C33 C34 C35 -7.0(3) . . . . ?
C31 C33 C34 C35 -178.62(17) . . . . ?
C39 C34 C35 C36 -0.4(3) . . . . ?
C33 C34 C35 C36 178.19(18) . . . . ?
C34 C35 C36 C37 0.1(3) . . . . ?
C35 C36 C37 C38 0.1(3) . . . . ?
C36 C37 C38 C39 0.1(3) . . . . ?
C37 C38 C39 C34 -0.4(3) . . . . ?
C35 C34 C39 C38 0.6(3) . . . . ?
C33 C34 C39 C38 -177.99(19) . . . . ?
C42 N6 C40 N4 -17.2(3) . . . . ?
C41 N6 C40 N4 147.00(19) . . . . ?
C42 N6 C40 N5 163.74(17) . . . . ?
C41 N6 C40 N5 -32.0(3) . . . . ?
C44 N5 C40 N4 -9.8(3) . . . . ?
C43 N5 C40 N4 140.52(19) . . . . ?
C44 N5 C40 N6 169.21(17) . . . . ?
C43 N5 C40 N6 -40.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O1 0.85(2) 2.02(2) 2.845(2) 166(2) .
N1 H1A O1 0.91(2) 1.86(2) 2.752(2) 167.6(19) 2_765
N4 H4A O3 0.96(2) 1.79(2) 2.741(2) 169(2) 1_545
N4 H4B O3 0.95(2) 1.87(2) 2.789(2) 161.5(19) 2_666
O5 H5A O4 0.853(17) 2.1732(14) 2.887(17) 141.0(11) 1_545

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Evaporation of DCM solution under nitrogen'
_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_JB012
_database_code_depnum_ccdc_archive 'CCDC 1849342'
_audit_update_record             
;
2018-06-14 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        
;
8-Benzoyl-naphth-1-ol
;
_chemical_name_common            ?
_chemical_melting_point          448
_chemical_formula_moiety         'C17 H12 O2'
_chemical_formula_sum            'C17 H12 O2'
_chemical_formula_weight         248.27

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      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

_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, y, z+1/2'
'x, -y, z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'

_cell_length_a                   17.3065(5)
_cell_length_b                   17.6303(4)
_cell_length_c                   8.0817(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2465.88(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    6914
_cell_measurement_theta_min      3.6130
_cell_measurement_theta_max      29.2050

_exptl_crystal_description       Block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.136
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            13194
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.299
_diffrn_reflns_theta_max         29.276
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3039
_reflns_number_gt                2920
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_max     0.870
_reflns_Friedel_fraction_full    0.990

_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+1.0323P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1234 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3039
_refine_ls_number_parameters     176
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
O1 O 0.18246(8) 0.27918(7) 0.20593(17) 0.0233(3) Uani 1 1 d . . . . .
O2 O 0.26317(7) 0.14599(8) 0.44339(16) 0.0229(3) Uani 1 1 d . . . . .
C1 C 0.14659(10) 0.32425(10) 0.3163(2) 0.0185(4) Uani 1 1 d . . . . .
C2 C 0.12967(11) 0.39954(11) 0.2876(2) 0.0230(4) Uani 1 1 d . . . . .
H2 H 0.144114 0.422483 0.185793 0.028 Uiso 1 1 calc R U . . .
C3 C 0.09109(11) 0.44234(11) 0.4087(3) 0.0265(4) Uani 1 1 d . . . . .
H3 H 0.079888 0.494226 0.388013 0.032 Uiso 1 1 calc R U . . .
C4 C 0.06945(12) 0.41073(11) 0.5555(2) 0.0247(4) Uani 1 1 d . . . . .
H4 H 0.041636 0.440133 0.633951 0.030 Uiso 1 1 calc R U . . .
C5 C 0.08824(10) 0.33413(10) 0.5918(2) 0.0198(4) Uani 1 1 d . . . . .
C6 C 0.07228(11) 0.30218(11) 0.7491(2) 0.0232(4) Uani 1 1 d . . . . .
H6 H 0.044497 0.330970 0.828657 0.028 Uiso 1 1 calc R U . . .
C7 C 0.09624(12) 0.23077(11) 0.7876(2) 0.0240(4) Uani 1 1 d . . . . .
H7 H 0.086175 0.210576 0.894401 0.029 Uiso 1 1 calc R U . . .
C8 C 0.13588(11) 0.18676(10) 0.6696(2) 0.0213(4) Uani 1 1 d . . . . .
H8 H 0.152761 0.137207 0.698294 0.026 Uiso 1 1 calc R U . . .
C9 C 0.15062(10) 0.21432(10) 0.5132(2) 0.0171(3) Uani 1 1 d . . . . .
C10 C 0.12749(10) 0.28967(10) 0.4712(2) 0.0169(3) Uani 1 1 d . . . . .
C11 C 0.19695(10) 0.16257(10) 0.4025(2) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.16127(10) 0.12417(9) 0.2580(2) 0.0171(3) Uani 1 1 d . . . . .
C13 C 0.20857(11) 0.08238(10) 0.1516(2) 0.0213(4) Uani 1 1 d . . . . .
H13 H 0.262754 0.080580 0.169969 0.026 Uiso 1 1 calc R U . . .
C14 C 0.17650(12) 0.04352(10) 0.0191(2) 0.0241(4) Uani 1 1 d . . . . .
H14 H 0.208665 0.015147 -0.053259 0.029 Uiso 1 1 calc R U . . .
C15 C 0.09730(11) 0.04617(10) -0.0074(2) 0.0242(4) Uani 1 1 d . . . . .
H15 H 0.075328 0.019441 -0.097964 0.029 Uiso 1 1 calc R U . . .
C16 C 0.05009(11) 0.08768(10) 0.0978(2) 0.0227(4) Uani 1 1 d . . . . .
H16 H -0.004118 0.089032 0.079452 0.027 Uiso 1 1 calc R U . . .
C17 C 0.08192(10) 0.12718(10) 0.2295(2) 0.0197(4) Uani 1 1 d . . . . .
H17 H 0.049655 0.156275 0.300346 0.024 Uiso 1 1 calc R U . . .
H1 H 0.1986(17) 0.3055(15) 0.123(4) 0.042(8) 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
O1 C1 1.346(2) . ?
O1 H1 0.86(3) . ?
O2 C11 1.228(2) . ?
C1 C2 1.379(2) . ?
C1 C10 1.432(2) . ?
C2 C3 1.405(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.363(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.417(3) . ?
C5 C10 1.423(2) . ?
C6 C7 1.362(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.408(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.428(2) . ?
C9 C11 1.509(2) . ?
C11 C12 1.484(2) . ?
C12 C17 1.393(2) . ?
C12 C13 1.397(2) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 110.3(18) . . ?
O1 C1 C2 123.69(17) . . ?
O1 C1 C10 115.76(15) . . ?
C2 C1 C10 120.54(17) . . ?
C1 C2 C3 120.04(17) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 121.17(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.39(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 121.25(18) . . ?
C6 C5 C10 119.22(17) . . ?
C4 C5 C10 119.45(18) . . ?
C7 C6 C5 120.87(17) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.21(17) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 121.15(17) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.59(16) . . ?
C8 C9 C11 115.42(16) . . ?
C10 C9 C11 124.80(15) . . ?
C5 C10 C9 118.92(16) . . ?
C5 C10 C1 118.34(16) . . ?
C9 C10 C1 122.62(15) . . ?
O2 C11 C12 119.44(16) . . ?
O2 C11 C9 118.70(16) . . ?
C12 C11 C9 121.42(15) . . ?
C17 C12 C13 119.72(17) . . ?
C17 C12 C11 121.50(16) . . ?
C13 C12 C11 118.75(16) . . ?
C14 C13 C12 120.07(17) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.86(17) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.30(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.08(17) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 119.95(17) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.13(17) . . . . ?
C10 C1 C2 C3 -2.1(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 2.5(3) . . . . ?
C3 C4 C5 C6 174.42(18) . . . . ?
C3 C4 C5 C10 -2.2(3) . . . . ?
C4 C5 C6 C7 -174.46(18) . . . . ?
C10 C5 C6 C7 2.2(3) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 2.0(3) . . . . ?
C7 C8 C9 C11 177.13(17) . . . . ?
C6 C5 C10 C9 -0.8(2) . . . . ?
C4 C5 C10 C9 175.88(17) . . . . ?
C6 C5 C10 C1 -176.83(16) . . . . ?
C4 C5 C10 C1 -0.1(2) . . . . ?
C8 C9 C10 C5 -1.2(2) . . . . ?
C11 C9 C10 C5 -175.88(17) . . . . ?
C8 C9 C10 C1 174.61(17) . . . . ?
C11 C9 C10 C1 -0.1(3) . . . . ?
O1 C1 C10 C5 -178.90(15) . . . . ?
C2 C1 C10 C5 2.3(2) . . . . ?
O1 C1 C10 C9 5.3(2) . . . . ?
C2 C1 C10 C9 -173.56(17) . . . . ?
C8 C9 C11 O2 -62.6(2) . . . . ?
C10 C9 C11 O2 112.3(2) . . . . ?
C8 C9 C11 C12 109.72(18) . . . . ?
C10 C9 C11 C12 -75.4(2) . . . . ?
O2 C11 C12 C17 164.75(17) . . . . ?
C9 C11 C12 C17 -7.5(2) . . . . ?
O2 C11 C12 C13 -13.4(2) . . . . ?
C9 C11 C12 C13 174.35(16) . . . . ?
C17 C12 C13 C14 -0.6(3) . . . . ?
C11 C12 C13 C14 177.56(16) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C12 -1.1(3) . . . . ?
C13 C12 C17 C16 1.1(3) . . . . ?
C11 C12 C17 C16 -176.95(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.86(3) 1.81(3) 2.6697(19) 175(3) 6_554

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.035

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_JB200
_database_code_depnum_ccdc_archive 'CCDC 1849344'
_audit_update_record             
;
2018-06-14 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        
;
8-Acetylnaphth-1-ol 
;
_chemical_name_common            ?
_chemical_melting_point          355-357
_chemical_formula_moiety         'C12 H10 O2'
_chemical_formula_sum            'C12 H10 O2'
_chemical_formula_weight         186.20

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

_cell_length_a                   9.9122(2)
_cell_length_b                   13.8433(3)
_cell_length_c                   13.9018(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1907.57(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    6878
_cell_measurement_theta_min      3.8620
_cell_measurement_theta_max      28.9910

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.132
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            17220
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.280
_diffrn_reflns_theta_max         29.330
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4651
_reflns_number_gt                4090
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_max     0.842
_reflns_Friedel_fraction_full    0.992

_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.2272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4651
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
O1 O 0.52401(16) 0.88217(11) -0.12121(12) 0.0322(4) Uani 1 1 d . . . . .
O2 O 0.32653(15) 0.87473(10) -0.30477(11) 0.0281(3) Uani 1 1 d . . . . .
O3 O 0.31147(16) 0.95737(11) 0.19833(11) 0.0269(3) Uani 1 1 d . . . . .
O4 O 0.50533(16) 0.81951(12) 0.06528(11) 0.0360(4) Uani 1 1 d . . . . .
C1 C 0.6145(2) 0.95559(15) -0.13403(15) 0.0272(5) Uani 1 1 d . . . . .
C2 C 0.7004(3) 0.98619(17) -0.06345(17) 0.0352(5) Uani 1 1 d . . . . .
H2 H 0.701042 0.954765 -0.002698 0.042 Uiso 1 1 calc R U . . .
C3 C 0.7881(3) 1.06439(18) -0.08086(19) 0.0405(6) Uani 1 1 d . . . . .
H3 H 0.850265 1.083388 -0.032378 0.049 Uiso 1 1 calc R U . . .
C4 C 0.7855(2) 1.11305(18) -0.16557(18) 0.0366(5) Uani 1 1 d . . . . .
H4 H 0.844301 1.166312 -0.175562 0.044 Uiso 1 1 calc R U . . .
C5 C 0.6951(2) 1.08436(15) -0.23904(16) 0.0280(5) Uani 1 1 d . . . . .
C6 C 0.6818(2) 1.13843(16) -0.32530(17) 0.0315(5) Uani 1 1 d . . . . .
H6 H 0.738249 1.192856 -0.335836 0.038 Uiso 1 1 calc R U . . .
C7 C 0.5890(2) 1.11328(17) -0.39321(16) 0.0321(5) Uani 1 1 d . . . . .
H7 H 0.577165 1.152610 -0.448571 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5108(2) 1.02962(16) -0.38171(16) 0.0279(5) Uani 1 1 d . . . . .
H8 H 0.448719 1.011595 -0.430567 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5229(2) 0.97334(14) -0.30067(15) 0.0235(4) Uani 1 1 d . . . . .
C10 C 0.6117(2) 1.00199(15) -0.22530(15) 0.0245(4) Uani 1 1 d . . . . .
C11 C 0.4493(2) 0.87842(15) -0.30199(15) 0.0244(4) Uani 1 1 d . . . . .
C12 C 0.5349(2) 0.79032(16) -0.31331(18) 0.0343(5) Uani 1 1 d . . . . .
H12A H 0.483508 0.733259 -0.293325 0.051 Uiso 1 1 calc R U . . .
H12B H 0.615715 0.796456 -0.273185 0.051 Uiso 1 1 calc R U . . .
H12C H 0.561531 0.783439 -0.380848 0.051 Uiso 1 1 calc R U . . .
C13 C 0.3037(2) 0.91388(14) 0.28619(14) 0.0231(4) Uani 1 1 d . . . . .
C14 C 0.2492(2) 0.95837(16) 0.36493(16) 0.0304(5) Uani 1 1 d . . . . .
H14 H 0.212994 1.021678 0.359353 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2465(3) 0.91059(18) 0.45404(16) 0.0352(5) Uani 1 1 d . . . . .
H15 H 0.205950 0.941231 0.507916 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3011(3) 0.82123(17) 0.46428(16) 0.0343(5) Uani 1 1 d . . . . .
H16 H 0.301258 0.790895 0.525572 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3580(2) 0.77299(16) 0.38407(16) 0.0280(5) Uani 1 1 d . . . . .
C18 C 0.4116(2) 0.67878(17) 0.39176(18) 0.0366(6) Uani 1 1 d . . . . .
H18 H 0.413802 0.648105 0.452873 0.044 Uiso 1 1 calc R U . . .
C19 C 0.4598(3) 0.63132(18) 0.3141(2) 0.0436(6) Uani 1 1 d . . . . .
H19 H 0.494767 0.567806 0.321177 0.052 Uiso 1 1 calc R U . . .
C20 C 0.4587(3) 0.67537(17) 0.22274(18) 0.0377(6) Uani 1 1 d . . . . .
H20 H 0.493482 0.641450 0.168749 0.045 Uiso 1 1 calc R U . . .
C21 C 0.4079(2) 0.76694(15) 0.21103(15) 0.0254(4) Uani 1 1 d . . . . .
C22 C 0.35632(19) 0.81844(14) 0.29183(14) 0.0222(4) Uani 1 1 d . . . . .
C23 C 0.4014(2) 0.80320(14) 0.10926(15) 0.0247(4) Uani 1 1 d . . . . .
C24 C 0.2666(2) 0.80398(17) 0.06123(16) 0.0312(5) Uani 1 1 d . . . . .
H24A H 0.269159 0.847529 0.005684 0.047 Uiso 1 1 calc R U . . .
H24B H 0.198011 0.826379 0.106851 0.047 Uiso 1 1 calc R U . . .
H24C H 0.244137 0.738531 0.039636 0.047 Uiso 1 1 calc R U . . .
H1A H 0.521(3) 0.863(2) -0.062(2) 0.053(9) Uiso 1 1 d . . . . .
H3A H 0.262(3) 1.013(3) 0.201(2) 0.070(10) 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
O1 C1 1.367(3) . ?
O1 H1A 0.86(3) . ?
O2 C11 1.219(3) . ?
O3 C13 1.364(2) . ?
O3 H3A 0.92(4) . ?
O4 C23 1.219(3) . ?
C1 C2 1.367(3) . ?
C1 C10 1.422(3) . ?
C2 C3 1.409(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.357(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.420(3) . ?
C5 C10 1.421(3) . ?
C6 C7 1.363(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.425(3) . ?
C9 C11 1.503(3) . ?
C11 C12 1.494(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.367(3) . ?
C13 C22 1.423(3) . ?
C14 C15 1.405(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.358(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.417(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.412(3) . ?
C17 C22 1.428(3) . ?
C18 C19 1.351(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.409(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.425(3) . ?
C21 C23 1.503(3) . ?
C23 C24 1.494(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C1 O1 H1A 112(2) . . ?
C13 O3 H3A 108(2) . . ?
O1 C1 C2 123.1(2) . . ?
O1 C1 C10 116.07(19) . . ?
C2 C1 C10 120.8(2) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 C10 119.7(2) . . ?
C6 C5 C10 118.8(2) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.91(19) . . ?
C8 C9 C11 116.30(19) . . ?
C10 C9 C11 123.52(18) . . ?
C1 C10 C9 122.83(19) . . ?
C1 C10 C5 118.11(19) . . ?
C9 C10 C5 118.93(19) . . ?
O2 C11 C12 122.0(2) . . ?
O2 C11 C9 121.44(19) . . ?
C12 C11 C9 116.09(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 122.70(19) . . ?
O3 C13 C22 116.02(18) . . ?
C14 C13 C22 121.28(19) . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 121.7(2) . . ?
C18 C17 C22 118.6(2) . . ?
C16 C17 C22 119.6(2) . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 120.5(2) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 C23 115.8(2) . . ?
C22 C21 C23 124.04(18) . . ?
C21 C22 C13 123.54(18) . . ?
C21 C22 C17 118.89(18) . . ?
C13 C22 C17 117.56(18) . . ?
O4 C23 C24 122.04(19) . . ?
O4 C23 C21 119.9(2) . . ?
C24 C23 C21 117.49(19) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.0(2) . . . . ?
C10 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 2.7(4) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 174.7(2) . . . . ?
C3 C4 C5 C10 -2.8(3) . . . . ?
C4 C5 C6 C7 -176.3(2) . . . . ?
C10 C5 C6 C7 1.3(3) . . . . ?
C5 C6 C7 C8 -4.1(3) . . . . ?
C6 C7 C8 C9 2.2(3) . . . . ?
C7 C8 C9 C10 2.6(3) . . . . ?
C7 C8 C9 C11 -171.63(19) . . . . ?
O1 C1 C10 C9 -1.4(3) . . . . ?
C2 C1 C10 C9 -179.3(2) . . . . ?
O1 C1 C10 C5 174.32(18) . . . . ?
C2 C1 C10 C5 -3.6(3) . . . . ?
C8 C9 C10 C1 170.36(19) . . . . ?
C11 C9 C10 C1 -15.9(3) . . . . ?
C8 C9 C10 C5 -5.3(3) . . . . ?
C11 C9 C10 C5 168.45(19) . . . . ?
C4 C5 C10 C1 5.1(3) . . . . ?
C6 C5 C10 C1 -172.5(2) . . . . ?
C4 C5 C10 C9 -179.0(2) . . . . ?
C6 C5 C10 C9 3.4(3) . . . . ?
C8 C9 C11 O2 -65.2(3) . . . . ?
C10 C9 C11 O2 120.8(2) . . . . ?
C8 C9 C11 C12 106.7(2) . . . . ?
C10 C9 C11 C12 -67.3(3) . . . . ?
O3 C13 C14 C15 -178.7(2) . . . . ?
C22 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C16 1.9(4) . . . . ?
C14 C15 C16 C17 -2.2(4) . . . . ?
C15 C16 C17 C18 -177.9(2) . . . . ?
C15 C16 C17 C22 -0.7(3) . . . . ?
C16 C17 C18 C19 176.8(2) . . . . ?
C22 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
C19 C20 C21 C23 -175.1(2) . . . . ?
C20 C21 C22 C13 179.1(2) . . . . ?
C23 C21 C22 C13 -5.8(3) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
C23 C21 C22 C17 174.7(2) . . . . ?
O3 C13 C22 C21 -3.5(3) . . . . ?
C14 C13 C22 C21 176.6(2) . . . . ?
O3 C13 C22 C17 176.00(17) . . . . ?
C14 C13 C22 C17 -3.9(3) . . . . ?
C18 C17 C22 C21 0.4(3) . . . . ?
C16 C17 C22 C21 -176.9(2) . . . . ?
C18 C17 C22 C13 -179.06(19) . . . . ?
C16 C17 C22 C13 3.6(3) . . . . ?
C20 C21 C23 O4 -67.7(3) . . . . ?
C22 C21 C23 O4 117.1(2) . . . . ?
C20 C21 C23 C24 103.5(2) . . . . ?
C22 C21 C23 C24 -71.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O4 0.86(3) 1.88(3) 2.740(2) 177(3) .
O3 H3A O2 0.92(4) 1.79(4) 2.697(2) 174(3) 2_575

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.037


#==END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
####################################################################### 
# 
# 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_JB232
_database_code_depnum_ccdc_archive 'CCDC 1849345'
_audit_update_record             
;
2018-06-14 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 bis(dimethylamino)methaniminium 8-acetylnaphthalen-1-olate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H23 N3 O2'
_chemical_formula_sum            'C17 H23 N3 O2'
_chemical_formula_weight         301.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   15.1117(6)
_cell_length_b                   15.6707(7)
_cell_length_c                   16.4672(7)
_cell_angle_alpha                80.552(4)
_cell_angle_beta                 69.591(4)
_cell_angle_gamma                61.179(4)
_cell_volume                     3202.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    4795
_cell_measurement_theta_min      3.9820
_cell_measurement_theta_max      29.2150

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.158
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            16533
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.239
_diffrn_reflns_theta_max         29.251
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.672
_diffrn_measured_fraction_theta_full 0.829
_diffrn_reflns_Laue_measured_fraction_max 0.672
_diffrn_reflns_Laue_measured_fraction_full 0.829
_diffrn_reflns_point_group_measured_fraction_max 0.672
_diffrn_reflns_point_group_measured_fraction_full 0.829
_reflns_number_total             11729
_reflns_number_gt                8260
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11729
_refine_ls_number_parameters     845
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
O1A O 0.34690(11) 0.00425(10) 0.34402(10) 0.0256(4) Uani 1 1 d . . . . .
O1B O 0.43795(10) 0.52836(10) 0.13235(9) 0.0173(3) Uani 1 1 d . . . . .
O1C O 0.78071(10) 0.06119(10) 0.37637(10) 0.0212(3) Uani 1 1 d . . . . .
O1D O 0.93114(10) 0.53732(10) 0.12839(9) 0.0181(3) Uani 1 1 d . . . . .
O2A O 0.53993(11) -0.01206(11) 0.17627(11) 0.0292(4) Uani 1 1 d . . . . .
O2B O 0.47829(11) 0.71324(11) 0.10334(10) 0.0261(4) Uani 1 1 d . . . . .
O2C O 1.02309(11) -0.05594(11) 0.24373(11) 0.0331(4) Uani 1 1 d . . . . .
O2D O 0.98345(11) 0.71153(11) 0.10581(10) 0.0251(4) Uani 1 1 d . . . . .
N1A N 0.59075(12) -0.16529(13) 0.41943(11) 0.0210(4) Uani 1 1 d . . . . .
N1B N 0.28366(12) 0.78235(12) 0.04616(11) 0.0166(4) Uani 1 1 d . . . . .
N1C N 0.90159(12) 0.16735(13) 0.45596(12) 0.0210(4) Uani 1 1 d . . . . .
N1D N 0.07934(12) 0.23753(12) 0.11285(11) 0.0170(4) Uani 1 1 d . . . . .
N2A N 0.41182(13) -0.06702(14) 0.48773(13) 0.0192(4) Uani 1 1 d . . . . .
N2B N 0.40520(14) 0.63069(13) -0.01538(13) 0.0176(4) Uani 1 1 d . . . . .
N2C N 0.82267(17) 0.06803(15) 0.52043(15) 0.0286(5) Uani 1 1 d . . . . .
N2D N 0.08174(14) 0.36845(13) 0.02509(14) 0.0187(4) Uani 1 1 d . . . . .
N3A N 0.52780(12) -0.14645(12) 0.56820(12) 0.0194(4) Uani 1 1 d . . . . .
N3B N 0.39951(12) 0.76964(12) -0.09311(11) 0.0153(4) Uani 1 1 d . . . . .
N3C N 0.81341(13) 0.17967(13) 0.60323(12) 0.0214(4) Uani 1 1 d . . . . .
N3D N 0.19872(12) 0.21173(12) -0.02632(11) 0.0196(4) Uani 1 1 d . . . . .
C1A C 0.28139(15) 0.09734(16) 0.35033(15) 0.0208(5) Uani 1 1 d . . . . .
C1B C 0.39994(14) 0.52980(14) 0.21665(13) 0.0163(5) Uani 1 1 d . . . . .
C1C C 0.74861(15) 0.14637(16) 0.34112(14) 0.0197(5) Uani 1 1 d . . . . .
C1D C 0.89069(14) 0.54135(14) 0.21281(13) 0.0166(5) Uani 1 1 d . . . . .
C2A C 0.20363(16) 0.14276(16) 0.42711(15) 0.0255(5) Uani 1 1 d . . . . .
H2A H 0.1979 0.1050 0.4783 0.031 Uiso 1 1 calc R U . . .
C2B C 0.32793(14) 0.49408(15) 0.26269(14) 0.0192(5) Uani 1 1 d . . . . .
H2B H 0.2982 0.4743 0.2318 0.023 Uiso 1 1 calc R U . . .
C2C C 0.66609(15) 0.23183(16) 0.38624(16) 0.0249(5) Uani 1 1 d . . . . .
H2C H 0.6334 0.2278 0.4466 0.030 Uiso 1 1 calc R U . . .
C2D C 0.80798(14) 0.51858(15) 0.25789(14) 0.0197(5) Uani 1 1 d . . . . .
H2D H 0.7716 0.5082 0.2267 0.024 Uiso 1 1 calc R U . . .
C3A C 0.13391(17) 0.24229(18) 0.43086(17) 0.0311(6) Uani 1 1 d . . . . .
H3A H 0.0822 0.2705 0.4846 0.037 Uiso 1 1 calc R U . . .
C3B C 0.29831(15) 0.48663(15) 0.35306(14) 0.0203(5) Uani 1 1 d . . . . .
H3B H 0.2512 0.4596 0.3820 0.024 Uiso 1 1 calc R U . . .
C3C C 0.63065(17) 0.32106(17) 0.34658(17) 0.0292(6) Uani 1 1 d . . . . .
H3C H 0.5739 0.3764 0.3801 0.035 Uiso 1 1 calc R U . . .
C3D C 0.77728(15) 0.51073(16) 0.34859(15) 0.0227(5) Uani 1 1 d . . . . .
H3D H 0.7219 0.4932 0.3773 0.027 Uiso 1 1 calc R U . . .
C4A C 0.13776(16) 0.30000(17) 0.35995(18) 0.0307(6) Uani 1 1 d . . . . .
H4A H 0.0889 0.3674 0.3642 0.037 Uiso 1 1 calc R U . . .
C4B C 0.33599(15) 0.51762(15) 0.40066(14) 0.0215(5) Uani 1 1 d . . . . .
H4B H 0.3166 0.5101 0.4618 0.026 Uiso 1 1 calc R U . . .
C4C C 0.67515(17) 0.33223(17) 0.25985(17) 0.0302(6) Uani 1 1 d . . . . .
H4C H 0.6487 0.3944 0.2335 0.036 Uiso 1 1 calc R U . . .
C4D C 0.82492(15) 0.52760(15) 0.39635(14) 0.0222(5) Uani 1 1 d . . . . .
H4D H 0.8044 0.5196 0.4574 0.027 Uiso 1 1 calc R U . . .
C5A C 0.21465(16) 0.25934(16) 0.27989(16) 0.0250(5) Uani 1 1 d . . . . .
C5B C 0.40351(14) 0.56060(15) 0.35907(14) 0.0180(5) Uani 1 1 d . . . . .
C5C C 0.76105(16) 0.25008(17) 0.20997(16) 0.0241(5) Uani 1 1 d . . . . .
C5D C 0.90457(14) 0.55698(15) 0.35517(14) 0.0177(5) Uani 1 1 d . . . . .
C6A C 0.22071(18) 0.31583(17) 0.20377(17) 0.0306(6) Uani 1 1 d . . . . .
H6A H 0.1715 0.3831 0.2062 0.037 Uiso 1 1 calc R U . . .
C6B C 0.44158(15) 0.59634(16) 0.40623(15) 0.0232(5) Uani 1 1 d . . . . .
H6B H 0.4213 0.5914 0.4676 0.028 Uiso 1 1 calc R U . . .
C6C C 0.81089(17) 0.25815(18) 0.12070(16) 0.0290(6) Uani 1 1 d . . . . .
H6C H 0.7846 0.3195 0.0931 0.035 Uiso 1 1 calc R U . . .
C6D C 0.95455(15) 0.57715(15) 0.40258(14) 0.0209(5) Uani 1 1 d . . . . .
H6D H 0.9355 0.5694 0.4637 0.025 Uiso 1 1 calc R U . . .
C7A C 0.29570(18) 0.27575(17) 0.12715(17) 0.0296(6) Uani 1 1 d . . . . .
H7A H 0.2975 0.3148 0.0766 0.035 Uiso 1 1 calc R U . . .
C7B C 0.50665(16) 0.63765(17) 0.36487(15) 0.0263(6) Uani 1 1 d . . . . .
H7B H 0.5329 0.6598 0.3973 0.032 Uiso 1 1 calc R U . . .
C7C C 0.89537(17) 0.18013(19) 0.07368(15) 0.0312(6) Uani 1 1 d . . . . .
H7C H 0.9283 0.1874 0.0140 0.037 Uiso 1 1 calc R U . . .
C7D C 1.02961(16) 0.60758(16) 0.36153(15) 0.0248(5) Uani 1 1 d . . . . .
H7D H 1.0643 0.6186 0.3939 0.030 Uiso 1 1 calc R U . . .
C8A C 0.37067(17) 0.17676(17) 0.12222(15) 0.0266(5) Uani 1 1 d . . . . .
H8A H 0.4241 0.1499 0.0688 0.032 Uiso 1 1 calc R U . . .
C8B C 0.53513(15) 0.64764(16) 0.27408(15) 0.0231(5) Uani 1 1 d . . . . .
H8B H 0.5793 0.6779 0.2457 0.028 Uiso 1 1 calc R U . . .
C8C C 0.93393(16) 0.08930(18) 0.11278(15) 0.0283(6) Uani 1 1 d . . . . .
H8C H 0.9933 0.0351 0.0794 0.034 Uiso 1 1 calc R U . . .
C8D C 1.05615(15) 0.62277(16) 0.27158(15) 0.0235(5) Uani 1 1 d . . . . .
H8D H 1.1069 0.6461 0.2439 0.028 Uiso 1 1 calc R U . . .
C9A C 0.36701(15) 0.11879(16) 0.19419(15) 0.0217(5) Uani 1 1 d . . . . .
C9B C 0.49995(14) 0.61427(15) 0.22621(14) 0.0171(5) Uani 1 1 d . . . . .
C9C C 0.88720(15) 0.07686(16) 0.19912(15) 0.0212(5) Uani 1 1 d . . . . .
C9D C 1.00967(14) 0.60422(14) 0.22380(14) 0.0174(5) Uani 1 1 d . . . . .
C10A C 0.28787(15) 0.15802(15) 0.27416(14) 0.0180(5) Uani 1 1 d . . . . .
C10B C 0.43431(14) 0.56851(14) 0.26676(14) 0.0156(5) Uani 1 1 d . . . . .
C10C C 0.79792(14) 0.15795(16) 0.24964(14) 0.0184(5) Uani 1 1 d . . . . .
H1 H 0.4531(16) 0.5930(16) -0.0611(16) 0.028(6) Uiso 1 1 d . . . . .
H2 H 0.0367(17) 0.4105(17) 0.0674(17) 0.037(7) Uiso 1 1 d . . . . .
H3 H 0.4058(18) 0.6041(18) 0.0347(18) 0.033(7) Uiso 1 1 d . . . . .
H4 H 0.8162(18) 0.0607(18) 0.4684(18) 0.044(8) Uiso 1 1 d . . . . .
H5 H 0.3559(17) -0.0600(16) 0.5372(16) 0.035(7) Uiso 1 1 d . . . . .
H6 H 0.3973(17) -0.0437(17) 0.4358(17) 0.034(7) Uiso 1 1 d . . . . .
H7 H 0.0860(18) 0.3929(19) -0.0278(18) 0.039(8) Uiso 1 1 d . . . . .
H8 H 0.798(2) 0.038(2) 0.568(2) 0.059(9) Uiso 1 1 d . . . . .
C10D C 0.93470(14) 0.56809(14) 0.26333(13) 0.0147(5) Uani 1 1 d . . . . .
C11A C 0.44755(16) 0.01316(16) 0.18312(14) 0.0215(5) Uani 1 1 d . . . . .
C11B C 0.52863(15) 0.63336(16) 0.13061(14) 0.0176(5) Uani 1 1 d . . . . .
C11C C 0.93505(16) -0.02370(16) 0.23528(14) 0.0238(5) Uani 1 1 d . . . . .
C11D C 1.03441(15) 0.63000(16) 0.12886(14) 0.0192(5) Uani 1 1 d . . . . .
C12A C 0.41465(17) -0.05576(16) 0.16527(16) 0.0281(6) Uani 1 1 d . . . . .
H12A H 0.4217 -0.0535 0.1036 0.042 Uiso 1 1 calc R U . . .
H12B H 0.3405 -0.0371 0.2000 0.042 Uiso 1 1 calc R U . . .
H12C H 0.4602 -0.1220 0.1805 0.042 Uiso 1 1 calc R U . . .
C12B C 0.62978(15) 0.55806(16) 0.07309(14) 0.0249(5) Uani 1 1 d . . . . .
H12D H 0.6289 0.5692 0.0130 0.037 Uiso 1 1 calc R U . . .
H12E H 0.6362 0.4931 0.0912 0.037 Uiso 1 1 calc R U . . .
H12F H 0.6904 0.5627 0.0774 0.037 Uiso 1 1 calc R U . . .
C12C C 0.88392(18) -0.08716(17) 0.24523(17) 0.0326(6) Uani 1 1 d . . . . .
H12G H 0.9142 -0.1251 0.1920 0.049 Uiso 1 1 calc R U . . .
H12H H 0.8073 -0.0467 0.2562 0.049 Uiso 1 1 calc R U . . .
H12I H 0.8966 -0.1315 0.2940 0.049 Uiso 1 1 calc R U . . .
C12D C 1.13388(15) 0.55624(16) 0.06772(15) 0.0267(6) Uani 1 1 d . . . . .
H12J H 1.1351 0.5758 0.0078 0.040 Uiso 1 1 calc R U . . .
H12K H 1.1351 0.4923 0.0783 0.040 Uiso 1 1 calc R U . . .
H12L H 1.1962 0.5525 0.0772 0.040 Uiso 1 1 calc R U . . .
C13A C 0.57538(17) -0.17001(17) 0.33827(15) 0.0275(6) Uani 1 1 d . . . . .
H13A H 0.5065 -0.1687 0.3502 0.041 Uiso 1 1 calc R U . . .
H13B H 0.6323 -0.2304 0.3076 0.041 Uiso 1 1 calc R U . . .
H13C H 0.5769 -0.1140 0.3023 0.041 Uiso 1 1 calc R U . . .
C13B C 0.22704(15) 0.73946(15) 0.11537(14) 0.0230(5) Uani 1 1 d . . . . .
H13D H 0.2190 0.6916 0.0909 0.035 Uiso 1 1 calc R U . . .
H13E H 0.1567 0.7907 0.1455 0.035 Uiso 1 1 calc R U . . .
H13F H 0.2672 0.7071 0.1565 0.035 Uiso 1 1 calc R U . . .
C13C C 0.86989(17) 0.27021(16) 0.43705(15) 0.0279(6) Uani 1 1 d . . . . .
H13G H 0.8419 0.2886 0.3879 0.042 Uiso 1 1 calc R U . . .
H13H H 0.9316 0.2821 0.4225 0.042 Uiso 1 1 calc R U . . .
H13I H 0.8147 0.3092 0.4880 0.042 Uiso 1 1 calc R U . . .
C13D C 0.14279(15) 0.14409(15) 0.14679(15) 0.0229(5) Uani 1 1 d . . . . .
H13J H 0.2156 0.1152 0.1069 0.034 Uiso 1 1 calc R U . . .
H13K H 0.1116 0.1003 0.1526 0.034 Uiso 1 1 calc R U . . .
H13L H 0.1438 0.1540 0.2036 0.034 Uiso 1 1 calc R U . . .
C14A C 0.69935(15) -0.18850(16) 0.41191(16) 0.0265(5) Uani 1 1 d . . . . .
H14A H 0.6992 -0.1646 0.4634 0.040 Uiso 1 1 calc R U . . .
H14B H 0.7277 -0.1572 0.3602 0.040 Uiso 1 1 calc R U . . .
H14C H 0.7440 -0.2592 0.4071 0.040 Uiso 1 1 calc R U . . .
C14B C 0.27630(16) 0.87137(15) 0.07057(15) 0.0235(5) Uani 1 1 d . . . . .
H14D H 0.3344 0.8831 0.0297 0.035 Uiso 1 1 calc R U . . .
H14E H 0.2815 0.8645 0.1292 0.035 Uiso 1 1 calc R U . . .
H14F H 0.2080 0.9264 0.0692 0.035 Uiso 1 1 calc R U . . .
C14C C 0.97352(16) 0.10316(17) 0.38160(15) 0.0284(6) Uani 1 1 d . . . . .
H14G H 0.9902 0.0356 0.3992 0.043 Uiso 1 1 calc R U . . .
H14H H 1.0392 0.1096 0.3593 0.043 Uiso 1 1 calc R U . . .
H14I H 0.9396 0.1210 0.3362 0.043 Uiso 1 1 calc R U . . .
C14D C -0.01716(15) 0.30135(16) 0.17766(14) 0.0225(5) Uani 1 1 d . . . . .
H14J H 0.0012 0.3300 0.2139 0.034 Uiso 1 1 calc R U . . .
H14K H -0.0526 0.2636 0.2140 0.034 Uiso 1 1 calc R U . . .
H14L H -0.0650 0.3534 0.1486 0.034 Uiso 1 1 calc R U . . .
C15A C 0.50899(15) -0.12621(15) 0.49174(14) 0.0174(5) Uani 1 1 d . . . . .
C15B C 0.36467(14) 0.72631(14) -0.02099(13) 0.0141(4) Uani 1 1 d . . . . .
C15C C 0.84471(15) 0.13835(15) 0.52708(15) 0.0205(5) Uani 1 1 d . . . . .
C15D C 0.11818(14) 0.27396(15) 0.03742(14) 0.0169(5) Uani 1 1 d . . . . .
C16A C 0.45438(16) -0.08337(16) 0.64288(14) 0.0227(5) Uani 1 1 d . . . . .
H16A H 0.4185 -0.0164 0.6233 0.034 Uiso 1 1 calc R U . . .
H16B H 0.4937 -0.0854 0.6801 0.034 Uiso 1 1 calc R U . . .
H16C H 0.4014 -0.1057 0.6756 0.034 Uiso 1 1 calc R U . . .
C16B C 0.49626(15) 0.71145(15) -0.16137(14) 0.0215(5) Uani 1 1 d . . . . .
H16D H 0.5481 0.6602 -0.1351 0.032 Uiso 1 1 calc R U . . .
H16E H 0.5264 0.7534 -0.1970 0.032 Uiso 1 1 calc R U . . .
H16F H 0.4791 0.6817 -0.1978 0.032 Uiso 1 1 calc R U . . .
C16C C 0.86948(17) 0.22453(17) 0.62260(16) 0.0269(5) Uani 1 1 d . . . . .
H16G H 0.9323 0.2160 0.5729 0.040 Uiso 1 1 calc R U . . .
H16H H 0.8916 0.1933 0.6736 0.040 Uiso 1 1 calc R U . . .
H16I H 0.8220 0.2942 0.6342 0.040 Uiso 1 1 calc R U . . .
C16D C 0.25956(16) 0.24749(16) -0.09952(15) 0.0277(6) Uani 1 1 d . . . . .
H16J H 0.2204 0.2778 -0.1415 0.042 Uiso 1 1 calc R U . . .
H16K H 0.3285 0.1930 -0.1272 0.042 Uiso 1 1 calc R U . . .
H16L H 0.2708 0.2958 -0.0792 0.042 Uiso 1 1 calc R U . . .
C17A C 0.60094(17) -0.24456(16) 0.58807(15) 0.0267(5) Uani 1 1 d . . . . .
H17A H 0.6348 -0.2863 0.5368 0.040 Uiso 1 1 calc R U . . .
H17B H 0.5614 -0.2715 0.6359 0.040 Uiso 1 1 calc R U . . .
H17C H 0.6556 -0.2416 0.6048 0.040 Uiso 1 1 calc R U . . .
C17B C 0.33221(15) 0.86525(15) -0.12139(14) 0.0207(5) Uani 1 1 d . . . . .
H17D H 0.2606 0.8912 -0.0794 0.031 Uiso 1 1 calc R U . . .
H17E H 0.3285 0.8593 -0.1783 0.031 Uiso 1 1 calc R U . . .
H17F H 0.3623 0.9095 -0.1254 0.031 Uiso 1 1 calc R U . . .
C17C C 0.73863(16) 0.16181(17) 0.67917(15) 0.0275(6) Uani 1 1 d . . . . .
H17G H 0.6878 0.1537 0.6612 0.041 Uiso 1 1 calc R U . . .
H17H H 0.7004 0.2172 0.7192 0.041 Uiso 1 1 calc R U . . .
H17I H 0.7775 0.1025 0.7082 0.041 Uiso 1 1 calc R U . . .
C17D C 0.20088(16) 0.12235(15) -0.04400(15) 0.0250(5) Uani 1 1 d . . . . .
H17J H 0.1401 0.1158 -0.0018 0.038 Uiso 1 1 calc R U . . .
H17K H 0.2670 0.0663 -0.0395 0.038 Uiso 1 1 calc R U . . .
H17L H 0.1970 0.1250 -0.1026 0.038 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
O1A C1A 1.306(2) . ?
O1A C11A 2.574(3) . ?
O1B C1B 1.304(2) . ?
O1B C11B 2.592(2) . ?
O1C C1C 1.293(3) . ?
O1C C11C 2.618(2) . ?
O1D C1D 1.307(2) . ?
O1D C11D 2.597(2) . ?
O2A C11A 1.221(2) . ?
O2B C11B 1.218(3) . ?
O2C C11C 1.226(2) . ?
O2D C11D 1.211(3) . ?
N1A C15A 1.343(2) . ?
N1A C13A 1.453(3) . ?
N1A C14A 1.462(2) . ?
N1B C15B 1.353(2) . ?
N1B C13B 1.451(2) . ?
N1B C14B 1.457(2) . ?
N1C C15C 1.348(3) . ?
N1C C14C 1.454(3) . ?
N1C C13C 1.456(3) . ?
N1D C15D 1.340(3) . ?
N1D C14D 1.458(2) . ?
N1D C13D 1.458(3) . ?
N2A C15A 1.325(3) . ?
N2A H5 0.92(2) . ?
N2A H6 0.93(3) . ?
N2B C15B 1.318(3) . ?
N2B H1 0.89(2) . ?
N2B H3 0.86(3) . ?
N2C C15C 1.325(3) . ?
N2C H4 0.93(3) . ?
N2C H8 0.91(3) . ?
N2D C15D 1.315(3) . ?
N2D H2 0.88(2) . ?
N2D H7 0.89(3) . ?
N3A C15A 1.341(3) . ?
N3A C16A 1.453(2) . ?
N3A C17A 1.463(3) . ?
N3B C15B 1.339(3) . ?
N3B C17B 1.459(3) . ?
N3B C16B 1.462(2) . ?
N3C C15C 1.332(3) . ?
N3C C17C 1.457(3) . ?
N3C C16C 1.466(3) . ?
N3D C15D 1.355(2) . ?
N3D C16D 1.454(3) . ?
N3D C17D 1.460(2) . ?
C1A C2A 1.392(3) . ?
C1A C10A 1.449(3) . ?
C1B C2B 1.395(3) . ?
C1B C10B 1.444(3) . ?
C1C C2C 1.404(3) . ?
C1C C10C 1.454(3) . ?
C1D C2D 1.392(3) . ?
C1D C10D 1.442(3) . ?
C2A C3A 1.396(3) . ?
C2A H2A 0.9500 . ?
C2B C3B 1.399(3) . ?
C2B H2B 0.9500 . ?
C2C C3C 1.375(3) . ?
C2C H2C 0.9500 . ?
C2D C3D 1.404(3) . ?
C2D H2D 0.9500 . ?
C3A C4A 1.357(4) . ?
C3A H3A 0.9500 . ?
C3B C4B 1.370(3) . ?
C3B H3B 0.9500 . ?
C3C C4C 1.373(4) . ?
C3C H3C 0.9500 . ?
C3D C4D 1.362(3) . ?
C3D H3D 0.9500 . ?
C4A C5A 1.410(3) . ?
C4A H4A 0.9500 . ?
C4B C5B 1.410(3) . ?
C4B H4B 0.9500 . ?
C4C C5C 1.417(3) . ?
C4C H4C 0.9500 . ?
C4D C5D 1.408(3) . ?
C4D H4D 0.9500 . ?
C5A C6A 1.413(3) . ?
C5A C10A 1.427(3) . ?
C5B C6B 1.419(3) . ?
C5B C10B 1.429(3) . ?
C5C C10C 1.411(3) . ?
C5C C6C 1.415(3) . ?
C5D C6D 1.415(3) . ?
C5D C10D 1.426(3) . ?
C6A C7A 1.359(3) . ?
C6A H6A 0.9500 . ?
C6B C7B 1.361(3) . ?
C6B H6B 0.9500 . ?
C6C C7C 1.357(3) . ?
C6C H6C 0.9500 . ?
C6D C7D 1.361(3) . ?
C6D H6D 0.9500 . ?
C7A C8A 1.407(3) . ?
C7A H7A 0.9500 . ?
C7B C8B 1.409(3) . ?
C7B H7B 0.9500 . ?
C7C C8C 1.393(3) . ?
C7C H7C 0.9500 . ?
C7D C8D 1.405(3) . ?
C7D H7D 0.9500 . ?
C8A C9A 1.372(3) . ?
C8A H8A 0.9500 . ?
C8B C9B 1.369(3) . ?
C8B H8B 0.9500 . ?
C8C C9C 1.378(3) . ?
C8C H8C 0.9500 . ?
C8D C9D 1.362(3) . ?
C8D H8D 0.9500 . ?
C9A C10A 1.414(3) . ?
C9A C11A 1.502(3) . ?
C9B C10B 1.418(3) . ?
C9B C11B 1.500(3) . ?
C9C C10C 1.428(3) . ?
C9C C11C 1.501(3) . ?
C9D C10D 1.418(3) . ?
C9D C11D 1.509(3) . ?
C11A C12A 1.491(3) . ?
C11B C12B 1.498(3) . ?
C11C C12C 1.487(3) . ?
C11D C12D 1.504(3) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C12C H12G 0.9800 . ?
C12C H12H 0.9800 . ?
C12C H12I 0.9800 . ?
C12D H12J 0.9800 . ?
C12D H12K 0.9800 . ?
C12D H12L 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C13C H13G 0.9800 . ?
C13C H13H 0.9800 . ?
C13C H13I 0.9800 . ?
C13D H13J 0.9800 . ?
C13D H13K 0.9800 . ?
C13D H13L 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C14C H14G 0.9800 . ?
C14C H14H 0.9800 . ?
C14C H14I 0.9800 . ?
C14D H14J 0.9800 . ?
C14D H14K 0.9800 . ?
C14D H14L 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C16C H16G 0.9800 . ?
C16C H16H 0.9800 . ?
C16C H16I 0.9800 . ?
C16D H16J 0.9800 . ?
C16D H16K 0.9800 . ?
C16D H16L 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C17C H17G 0.9800 . ?
C17C H17H 0.9800 . ?
C17C H17I 0.9800 . ?
C17D H17J 0.9800 . ?
C17D H17K 0.9800 . ?
C17D H17L 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
C1A O1A C11A 94.04(14) . . ?
C1B O1B C11B 93.16(12) . . ?
C1C O1C C11C 93.52(13) . . ?
C1D O1D C11D 92.45(12) . . ?
C15A N1A C13A 122.34(17) . . ?
C15A N1A C14A 122.17(18) . . ?
C13A N1A C14A 114.47(16) . . ?
C15B N1B C13B 119.86(16) . . ?
C15B N1B C14B 121.57(16) . . ?
C13B N1B C14B 114.33(16) . . ?
C15C N1C C14C 121.48(18) . . ?
C15C N1C C13C 121.23(17) . . ?
C14C N1C C13C 114.27(18) . . ?
C15D N1D C14D 120.21(18) . . ?
C15D N1D C13D 123.12(16) . . ?
C14D N1D C13D 114.07(18) . . ?
C15A N2A H5 117.2(15) . . ?
C15A N2A H6 122.9(14) . . ?
H5 N2A H6 118.5(19) . . ?
C15B N2B H1 120.7(15) . . ?
C15B N2B H3 118.6(16) . . ?
H1 N2B H3 116(2) . . ?
C15C N2C H4 118.4(16) . . ?
C15C N2C H8 121.6(18) . . ?
H4 N2C H8 118(2) . . ?
C15D N2D H2 121.9(16) . . ?
C15D N2D H7 120.5(17) . . ?
H2 N2D H7 115(2) . . ?
C15A N3A C16A 120.87(17) . . ?
C15A N3A C17A 121.21(17) . . ?
C16A N3A C17A 115.19(18) . . ?
C15B N3B C17B 123.36(16) . . ?
C15B N3B C16B 119.81(17) . . ?
C17B N3B C16B 114.14(17) . . ?
C15C N3C C17C 121.27(17) . . ?
C15C N3C C16C 122.71(17) . . ?
C17C N3C C16C 114.30(18) . . ?
C15D N3D C16D 119.92(17) . . ?
C15D N3D C17D 121.28(16) . . ?
C16D N3D C17D 114.28(17) . . ?
O1A C1A C2A 123.5(2) . . ?
O1A C1A C10A 119.36(18) . . ?
C2A C1A C10A 117.17(19) . . ?
O1B C1B C2B 123.55(19) . . ?
O1B C1B C10B 119.47(18) . . ?
C2B C1B C10B 116.98(19) . . ?
O1C C1C C2C 123.7(2) . . ?
O1C C1C C10C 120.31(18) . . ?
C2C C1C C10C 116.0(2) . . ?
O1D C1D C2D 123.44(19) . . ?
O1D C1D C10D 119.30(17) . . ?
C2D C1D C10D 117.24(19) . . ?
C1A C2A C3A 121.7(2) . . ?
C1A C2A H2A 119.1 . . ?
C3A C2A H2A 119.1 . . ?
C1B C2B C3B 121.8(2) . . ?
C1B C2B H2B 119.1 . . ?
C3B C2B H2B 119.1 . . ?
C3C C2C C1C 122.6(2) . . ?
C3C C2C H2C 118.7 . . ?
C1C C2C H2C 118.7 . . ?
C1D C2D C3D 121.2(2) . . ?
C1D C2D H2D 119.4 . . ?
C3D C2D H2D 119.4 . . ?
C4A C3A C2A 121.9(2) . . ?
C4A C3A H3A 119.0 . . ?
C2A C3A H3A 119.0 . . ?
C4B C3B C2B 121.3(2) . . ?
C4B C3B H3B 119.4 . . ?
C2B C3B H3B 119.4 . . ?
C4C C3C C2C 121.7(2) . . ?
C4C C3C H3C 119.1 . . ?
C2C C3C H3C 119.1 . . ?
C4D C3D C2D 121.64(19) . . ?
C4D C3D H3D 119.2 . . ?
C2D C3D H3D 119.2 . . ?
C3A C4A C5A 119.6(2) . . ?
C3A C4A H4A 120.2 . . ?
C5A C4A H4A 120.2 . . ?
C3B C4B C5B 120.1(2) . . ?
C3B C4B H4B 119.9 . . ?
C5B C4B H4B 119.9 . . ?
C3C C4C C5C 119.3(2) . . ?
C3C C4C H4C 120.4 . . ?
C5C C4C H4C 120.4 . . ?
C3D C4D C5D 120.0(2) . . ?
C3D C4D H4D 120.0 . . ?
C5D C4D H4D 120.0 . . ?
C4A C5A C6A 121.9(2) . . ?
C4A C5A C10A 119.8(2) . . ?
C6A C5A C10A 118.3(2) . . ?
C4B C5B C6B 121.9(2) . . ?
C4B C5B C10B 119.02(19) . . ?
C6B C5B C10B 119.09(19) . . ?
C10C C5C C6C 118.9(2) . . ?
C10C C5C C4C 119.6(2) . . ?
C6C C5C C4C 121.4(2) . . ?
C4D C5D C6D 121.8(2) . . ?
C4D C5D C10D 119.19(19) . . ?
C6D C5D C10D 119.03(18) . . ?
C7A C6A C5A 121.2(2) . . ?
C7A C6A H6A 119.4 . . ?
C5A C6A H6A 119.4 . . ?
C7B C6B C5B 121.0(2) . . ?
C7B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C7C C6C C5C 121.4(2) . . ?
C7C C6C H6C 119.3 . . ?
C5C C6C H6C 119.3 . . ?
C7D C6D C5D 120.7(2) . . ?
C7D C6D H6D 119.7 . . ?
C5D C6D H6D 119.7 . . ?
C6A C7A C8A 120.5(2) . . ?
C6A C7A H7A 119.8 . . ?
C8A C7A H7A 119.8 . . ?
C6B C7B C8B 120.1(2) . . ?
C6B C7B H7B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
C6C C7C C8C 120.1(2) . . ?
C6C C7C H7C 120.0 . . ?
C8C C7C H7C 120.0 . . ?
C6D C7D C8D 120.5(2) . . ?
C6D C7D H7D 119.8 . . ?
C8D C7D H7D 119.8 . . ?
C9A C8A C7A 120.4(2) . . ?
C9A C8A H8A 119.8 . . ?
C7A C8A H8A 119.8 . . ?
C9B C8B C7B 120.8(2) . . ?
C9B C8B H8B 119.6 . . ?
C7B C8B H8B 119.6 . . ?
C9C C8C C7C 121.0(2) . . ?
C9C C8C H8C 119.5 . . ?
C7C C8C H8C 119.5 . . ?
C9D C8D C7D 120.5(2) . . ?
C9D C8D H8D 119.8 . . ?
C7D C8D H8D 119.8 . . ?
C8A C9A C10A 120.3(2) . . ?
C8A C9A C11A 117.24(19) . . ?
C10A C9A C11A 122.4(2) . . ?
C8B C9B C10B 120.8(2) . . ?
C8B C9B C11B 117.16(19) . . ?
C10B C9B C11B 121.93(18) . . ?
C8C C9C C10C 119.8(2) . . ?
C8C C9C C11C 116.92(19) . . ?
C10C C9C C11C 123.3(2) . . ?
C8D C9D C10D 120.9(2) . . ?
C8D C9D C11D 117.97(18) . . ?
C10D C9D C11D 120.98(19) . . ?
C9A C10A C5A 119.2(2) . . ?
C9A C10A C1A 121.03(18) . . ?
C5A C10A C1A 119.74(19) . . ?
C9B C10B C5B 118.24(18) . . ?
C9B C10B C1B 121.30(19) . . ?
C5B C10B C1B 120.45(18) . . ?
C5C C10C C9C 118.8(2) . . ?
C5C C10C C1C 120.69(19) . . ?
C9C C10C C1C 120.5(2) . . ?
C9D C10D C5D 118.27(19) . . ?
C9D C10D C1D 121.55(19) . . ?
C5D C10D C1D 120.17(18) . . ?
O2A C11A C12A 121.47(19) . . ?
O2A C11A C9A 120.61(19) . . ?
C12A C11A C9A 117.04(18) . . ?
O2A C11A O1A 108.38(16) . . ?
C12A C11A O1A 87.21(14) . . ?
C9A C11A O1A 83.09(12) . . ?
O2B C11B C12B 121.6(2) . . ?
O2B C11B C9B 119.80(18) . . ?
C12B C11B C9B 117.9(2) . . ?
O2B C11B O1B 106.93(13) . . ?
C12B C11B O1B 88.45(12) . . ?
C9B C11B O1B 82.77(12) . . ?
O2C C11C C12C 121.4(2) . . ?
O2C C11C C9C 118.6(2) . . ?
C12C C11C C9C 119.14(19) . . ?
O2C C11C O1C 112.50(16) . . ?
C12C C11C O1C 84.40(13) . . ?
C9C C11C O1C 82.20(12) . . ?
O2D C11D C12D 122.0(2) . . ?
O2D C11D C9D 120.21(18) . . ?
C12D C11D C9D 117.1(2) . . ?
O2D C11D O1D 104.28(14) . . ?
C12D C11D O1D 90.83(12) . . ?
C9D C11D O1D 82.65(12) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11C C12C H12G 109.5 . . ?
C11C C12C H12H 109.5 . . ?
H12G C12C H12H 109.5 . . ?
C11C C12C H12I 109.5 . . ?
H12G C12C H12I 109.5 . . ?
H12H C12C H12I 109.5 . . ?
C11D C12D H12J 109.5 . . ?
C11D C12D H12K 109.5 . . ?
H12J C12D H12K 109.5 . . ?
C11D C12D H12L 109.5 . . ?
H12J C12D H12L 109.5 . . ?
H12K C12D H12L 109.5 . . ?
N1A C13A H13A 109.5 . . ?
N1A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
N1A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
N1B C13B H13D 109.5 . . ?
N1B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
N1B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
N1C C13C H13G 109.5 . . ?
N1C C13C H13H 109.5 . . ?
H13G C13C H13H 109.5 . . ?
N1C C13C H13I 109.5 . . ?
H13G C13C H13I 109.5 . . ?
H13H C13C H13I 109.5 . . ?
N1D C13D H13J 109.5 . . ?
N1D C13D H13K 109.5 . . ?
H13J C13D H13K 109.5 . . ?
N1D C13D H13L 109.5 . . ?
H13J C13D H13L 109.5 . . ?
H13K C13D H13L 109.5 . . ?
N1A C14A H14A 109.5 . . ?
N1A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
N1A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
N1B C14B H14D 109.5 . . ?
N1B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
N1B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
N1C C14C H14G 109.5 . . ?
N1C C14C H14H 109.5 . . ?
H14G C14C H14H 109.5 . . ?
N1C C14C H14I 109.5 . . ?
H14G C14C H14I 109.5 . . ?
H14H C14C H14I 109.5 . . ?
N1D C14D H14J 109.5 . . ?
N1D C14D H14K 109.5 . . ?
H14J C14D H14K 109.5 . . ?
N1D C14D H14L 109.5 . . ?
H14J C14D H14L 109.5 . . ?
H14K C14D H14L 109.5 . . ?
N2A C15A N3A 120.41(18) . . ?
N2A C15A N1A 120.8(2) . . ?
N3A C15A N1A 118.77(18) . . ?
N2B C15B N3B 121.37(18) . . ?
N2B C15B N1B 119.63(19) . . ?
N3B C15B N1B 118.96(18) . . ?
N2C C15C N3C 121.1(2) . . ?
N2C C15C N1C 119.6(2) . . ?
N3C C15C N1C 119.29(18) . . ?
N2D C15D N1D 121.39(18) . . ?
N2D C15D N3D 119.6(2) . . ?
N1D C15D N3D 118.96(19) . . ?
N3A C16A H16A 109.5 . . ?
N3A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
N3A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
N3B C16B H16D 109.5 . . ?
N3B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
N3B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
N3C C16C H16G 109.5 . . ?
N3C C16C H16H 109.5 . . ?
H16G C16C H16H 109.5 . . ?
N3C C16C H16I 109.5 . . ?
H16G C16C H16I 109.5 . . ?
H16H C16C H16I 109.5 . . ?
N3D C16D H16J 109.5 . . ?
N3D C16D H16K 109.5 . . ?
H16J C16D H16K 109.5 . . ?
N3D C16D H16L 109.5 . . ?
H16J C16D H16L 109.5 . . ?
H16K C16D H16L 109.5 . . ?
N3A C17A H17A 109.5 . . ?
N3A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
N3A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
N3B C17B H17D 109.5 . . ?
N3B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
N3B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
N3C C17C H17G 109.5 . . ?
N3C C17C H17H 109.5 . . ?
H17G C17C H17H 109.5 . . ?
N3C C17C H17I 109.5 . . ?
H17G C17C H17I 109.5 . . ?
H17H C17C H17I 109.5 . . ?
N3D C17D H17J 109.5 . . ?
N3D C17D H17K 109.5 . . ?
H17J C17D H17K 109.5 . . ?
N3D C17D H17L 109.5 . . ?
H17J C17D H17L 109.5 . . ?
H17K C17D H17L 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
C11A O1A C1A C2A -177.88(18) . . . . ?
C11A O1A C1A C10A 2.58(19) . . . . ?
C11B O1B C1B C2B 171.68(18) . . . . ?
C11B O1B C1B C10B -9.5(2) . . . . ?
C11C O1C C1C C2C -176.10(18) . . . . ?
C11C O1C C1C C10C 4.23(19) . . . . ?
C11D O1D C1D C2D 167.78(19) . . . . ?
C11D O1D C1D C10D -14.0(2) . . . . ?
O1A C1A C2A C3A -178.93(19) . . . . ?
C10A C1A C2A C3A 0.6(3) . . . . ?
O1B C1B C2B C3B 172.5(2) . . . . ?
C10B C1B C2B C3B -6.4(3) . . . . ?
O1C C1C C2C C3C -177.5(2) . . . . ?
C10C C1C C2C C3C 2.2(3) . . . . ?
O1D C1D C2D C3D 170.9(2) . . . . ?
C10D C1D C2D C3D -7.4(3) . . . . ?
C1A C2A C3A C4A 0.3(3) . . . . ?
C1B C2B C3B C4B 2.4(3) . . . . ?
C1C C2C C3C C4C -0.8(3) . . . . ?
C1D C2D C3D C4D 1.8(3) . . . . ?
C2A C3A C4A C5A -0.6(3) . . . . ?
C2B C3B C4B C5B 1.9(3) . . . . ?
C2C C3C C4C C5C -1.1(3) . . . . ?
C2D C3D C4D C5D 2.2(3) . . . . ?
C3A C4A C5A C6A 178.8(2) . . . . ?
C3A C4A C5A C10A -0.2(3) . . . . ?
C3B C4B C5B C6B 178.03(19) . . . . ?
C3B C4B C5B C10B -1.9(3) . . . . ?
C3C C4C C5C C10C 1.4(3) . . . . ?
C3C C4C C5C C6C -178.8(2) . . . . ?
C3D C4D C5D C6D 178.71(19) . . . . ?
C3D C4D C5D C10D -0.4(3) . . . . ?
C4A C5A C6A C7A 179.6(2) . . . . ?
C10A C5A C6A C7A -1.5(3) . . . . ?
C4B C5B C6B C7B -179.96(18) . . . . ?
C10B C5B C6B C7B -0.1(3) . . . . ?
C10C C5C C6C C7C -2.4(3) . . . . ?
C4C C5C C6C C7C 177.8(2) . . . . ?
C4D C5D C6D C7D -178.49(19) . . . . ?
C10D C5D C6D C7D 0.6(3) . . . . ?
C5A C6A C7A C8A -1.1(3) . . . . ?
C5B C6B C7B C8B 1.6(3) . . . . ?
C5C C6C C7C C8C 1.0(3) . . . . ?
C5D C6D C7D C8D 2.2(3) . . . . ?
C6A C7A C8A C9A 2.0(3) . . . . ?
C6B C7B C8B C9B -1.4(3) . . . . ?
C6C C7C C8C C9C 0.3(3) . . . . ?
C6D C7D C8D C9D -2.1(3) . . . . ?
C7A C8A C9A C10A -0.1(3) . . . . ?
C7A C8A C9A C11A 178.07(18) . . . . ?
C7B C8B C9B C10B -0.2(3) . . . . ?
C7B C8B C9B C11B 176.4(2) . . . . ?
C7C C8C C9C C10C 0.0(3) . . . . ?
C7C C8C C9C C11C -179.64(19) . . . . ?
C7D C8D C9D C10D -0.8(3) . . . . ?
C7D C8D C9D C11D 174.9(2) . . . . ?
C8A C9A C10A C5A -2.5(3) . . . . ?
C11A C9A C10A C5A 179.43(18) . . . . ?
C8A C9A C10A C1A 178.61(19) . . . . ?
C11A C9A C10A C1A 0.5(3) . . . . ?
C4A C5A C10A C9A -177.80(18) . . . . ?
C6A C5A C10A C9A 3.2(3) . . . . ?
C4A C5A C10A C1A 1.1(3) . . . . ?
C6A C5A C10A C1A -177.84(18) . . . . ?
O1A C1A C10A C9A -2.9(3) . . . . ?
C2A C1A C10A C9A 177.58(18) . . . . ?
O1A C1A C10A C5A 178.24(17) . . . . ?
C2A C1A C10A C5A -1.3(3) . . . . ?
C8B C9B C10B C5B 1.7(3) . . . . ?
C11B C9B C10B C5B -174.74(19) . . . . ?
C8B C9B C10B C1B -177.69(19) . . . . ?
C11B C9B C10B C1B 5.9(3) . . . . ?
C4B C5B C10B C9B 178.35(17) . . . . ?
C6B C5B C10B C9B -1.5(3) . . . . ?
C4B C5B C10B C1B -2.3(3) . . . . ?
C6B C5B C10B C1B 177.84(17) . . . . ?
O1B C1B C10B C9B 6.7(3) . . . . ?
C2B C1B C10B C9B -174.40(17) . . . . ?
O1B C1B C10B C5B -172.70(18) . . . . ?
C2B C1B C10B C5B 6.2(3) . . . . ?
C6C C5C C10C C9C 2.6(3) . . . . ?
C4C C5C C10C C9C -177.56(19) . . . . ?
C6C C5C C10C C1C -179.70(19) . . . . ?
C4C C5C C10C C1C 0.1(3) . . . . ?
C8C C9C C10C C5C -1.5(3) . . . . ?
C11C C9C C10C C5C 178.13(18) . . . . ?
C8C C9C C10C C1C -179.13(19) . . . . ?
C11C C9C C10C C1C 0.5(3) . . . . ?
O1C C1C C10C C5C 177.86(18) . . . . ?
C2C C1C C10C C5C -1.8(3) . . . . ?
O1C C1C C10C C9C -4.5(3) . . . . ?
C2C C1C C10C C9C 175.80(18) . . . . ?
C8D C9D C10D C5D 3.6(3) . . . . ?
C11D C9D C10D C5D -172.03(19) . . . . ?
C8D C9D C10D C1D -175.37(19) . . . . ?
C11D C9D C10D C1D 9.0(3) . . . . ?
C4D C5D C10D C9D 175.68(17) . . . . ?
C6D C5D C10D C9D -3.4(3) . . . . ?
C4D C5D C10D C1D -5.4(3) . . . . ?
C6D C5D C10D C1D 175.53(17) . . . . ?
O1D C1D C10D C9D 9.6(3) . . . . ?
C2D C1D C10D C9D -171.98(18) . . . . ?
O1D C1D C10D C5D -169.28(18) . . . . ?
C2D C1D C10D C5D 9.1(3) . . . . ?
C8A C9A C11A O2A 75.3(3) . . . . ?
C10A C9A C11A O2A -106.5(2) . . . . ?
C8A C9A C11A C12A -94.1(2) . . . . ?
C10A C9A C11A C12A 84.1(3) . . . . ?
C8A C9A C11A O1A -177.36(18) . . . . ?
C10A C9A C11A O1A 0.78(18) . . . . ?
C8B C9B C11B O2B -79.5(2) . . . . ?
C10B C9B C11B O2B 97.1(2) . . . . ?
C8B C9B C11B C12B 90.7(2) . . . . ?
C10B C9B C11B C12B -92.7(2) . . . . ?
C8B C9B C11B O1B 175.09(18) . . . . ?
C10B C9B C11B O1B -8.35(18) . . . . ?
C8C C9C C11C O2C 69.7(3) . . . . ?
C10C C9C C11C O2C -109.9(2) . . . . ?
C8C C9C C11C C12C -99.8(2) . . . . ?
C10C C9C C11C C12C 80.6(3) . . . . ?
C8C C9C C11C O1C -178.88(18) . . . . ?
C10C C9C C11C O1C 1.52(19) . . . . ?
C8D C9D C11D O2D -86.0(2) . . . . ?
C10D C9D C11D O2D 89.7(2) . . . . ?
C8D C9D C11D C12D 84.6(2) . . . . ?
C10D C9D C11D C12D -99.7(2) . . . . ?
C8D C9D C11D O1D 171.73(17) . . . . ?
C10D C9D C11D O1D -12.54(18) . . . . ?
C16A N3A C15A N2A -19.7(3) . . . . ?
C17A N3A C15A N2A 140.67(19) . . . . ?
C16A N3A C15A N1A 158.83(18) . . . . ?
C17A N3A C15A N1A -40.8(3) . . . . ?
C13A N1A C15A N2A -18.7(3) . . . . ?
C14A N1A C15A N2A 149.1(2) . . . . ?
C13A N1A C15A N3A 162.80(19) . . . . ?
C14A N1A C15A N3A -29.4(3) . . . . ?
C17B N3B C15B N2B 149.21(19) . . . . ?
C16B N3B C15B N2B -11.1(3) . . . . ?
C17B N3B C15B N1B -28.5(3) . . . . ?
C16B N3B C15B N1B 171.23(17) . . . . ?
C13B N1B C15B N2B -13.1(3) . . . . ?
C14B N1B C15B N2B 142.4(2) . . . . ?
C13B N1B C15B N3B 164.56(18) . . . . ?
C14B N1B C15B N3B -39.9(3) . . . . ?
C17C N3C C15C N2C -10.8(3) . . . . ?
C16C N3C C15C N2C 153.4(2) . . . . ?
C17C N3C C15C N1C 170.56(19) . . . . ?
C16C N3C C15C N1C -25.2(3) . . . . ?
C14C N1C C15C N2C -24.4(3) . . . . ?
C13C N1C C15C N2C 134.8(2) . . . . ?
C14C N1C C15C N3C 154.3(2) . . . . ?
C13C N1C C15C N3C -46.5(3) . . . . ?
C14D N1D C15D N2D 11.2(3) . . . . ?
C13D N1D C15D N2D -149.44(19) . . . . ?
C14D N1D C15D N3D -170.73(17) . . . . ?
C13D N1D C15D N3D 28.7(3) . . . . ?
C16D N3D C15D N2D 13.3(3) . . . . ?
C17D N3D C15D N2D -141.4(2) . . . . ?
C16D N3D C15D N1D -164.79(19) . . . . ?
C17D N3D C15D N1D 40.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13A H13A O1A 0.98 2.64 3.186(3) 115.7 .
C13A H13C O2A 0.98 2.46 3.329(3) 148.1 .
C13B H13E O2C 0.98 2.61 3.522(2) 155.5 1_465
C16C H16H O2C 0.98 2.39 3.303(3) 153.8 2_756
C16D H16K O2A 0.98 2.62 3.532(3) 155.5 2_655
C17B H17F O2A 0.98 2.54 3.497(2) 165.4 2_665
N2B H1 O1B 0.89(2) 2.02(2) 2.870(2) 160(2) 2_665
N2D H2 O1D 0.88(2) 2.00(2) 2.837(2) 160(2) 1_455
N2B H3 O1B 0.86(3) 1.90(3) 2.744(3) 168(2) .
N2C H4 O1C 0.93(3) 1.77(3) 2.691(3) 170(2) .
N2A H5 O1C 0.92(2) 2.07(2) 2.958(2) 163(2) 2_656
N2A H6 O1A 0.93(3) 1.82(3) 2.740(3) 170(2) .
N2D H7 O1D 0.89(3) 1.85(3) 2.729(3) 169(2) 2_665
N2C H8 O1A 0.91(3) 2.49(3) 3.288(3) 148(2) 2_656
C13A H13A O1A 0.98 2.64 3.186(3) 115.7 .
C13A H13C O2A 0.98 2.46 3.329(3) 148.1 .
C13B H13E O2C 0.98 2.61 3.522(2) 155.5 1_465
C16C H16H O2C 0.98 2.39 3.303(3) 153.8 2_756
C16D H16K O2A 0.98 2.62 3.532(3) 155.5 2_655
C17B H17F O2A 0.98 2.54 3.497(2) 165.4 2_665
N2B H1 O1B 0.89(2) 2.02(2) 2.870(2) 160(2) 2_665
N2D H2 O1D 0.88(2) 2.00(2) 2.837(2) 160(2) 1_455
N2B H3 O1B 0.86(3) 1.90(3) 2.744(3) 168(2) .
N2C H4 O1C 0.93(3) 1.77(3) 2.691(3) 170(2) .
N2A H5 O1C 0.92(2) 2.07(2) 2.958(2) 163(2) 2_656
N2A H6 O1A 0.93(3) 1.82(3) 2.740(3) 170(2) .
N2D H7 O1D 0.89(3) 1.85(3) 2.729(3) 169(2) 2_665
N2C H8 O1A 0.91(3) 2.49(3) 3.288(3) 148(2) 2_656

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3


_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_JB085
_database_code_depnum_ccdc_archive 'CCDC 1849617'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_vrf_PLAT355_JB085               
;
PROBLEM: Long O-H (X0.82, N0.98A) O1  -H1  1.02 Ang
RESPONSE: The hydrogen atom was located and refined. 
The hydrogen atom resides on hydroxyl with an O-H bond length
 of 1.02 Ang and hydrogen bond to N1 of 1.60 Ang. 
Although refined hydrogen atom positions from xray 
data are not very reliable, we note that the C-O bond length
is inconsistent with oxygen being deprotonated. Of course we
could have fixed the O-H bond length, but chose not to do it.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
"4-(dimethylamino)pyridine 1-(8'-hydroxynaphthalen-1'-yl)ethanonemolecular complex"
_chemical_name_common            ?
_chemical_melting_point          383-385
_chemical_formula_moiety         'C12 H10 O2 , C7 H10 N2'
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   27.588(4)
_cell_length_b                   8.2227(4)
_cell_length_c                   19.874(3)
_cell_angle_alpha                90
_cell_angle_beta                 132.66(3)
_cell_angle_gamma                90
_cell_volume                     3315.6(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    149.97(12)
_cell_measurement_reflns_used    1486
_cell_measurement_theta_min      3.9110
_cell_measurement_theta_max      25.8540

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.157
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      149.97(12)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7781
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.315
_diffrn_reflns_theta_max         29.361
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3819
_reflns_number_gt                2427
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.1644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3819
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
O1 O 0.12647(8) 0.57530(19) 0.35365(11) 0.0444(4) Uani 1 1 d . . . . .
C10 C 0.16155(9) 0.8195(3) 0.33489(12) 0.0311(5) Uani 1 1 d . . . . .
C9 C 0.20263(9) 0.7326(3) 0.32807(13) 0.0329(5) Uani 1 1 d . . . . .
C1 C 0.12262(10) 0.7399(3) 0.34839(14) 0.0357(5) Uani 1 1 d . . . . .
C5 C 0.15646(10) 0.9917(3) 0.32428(13) 0.0386(5) Uani 1 1 d . . . . .
N1 N 0.07231(9) 0.4334(2) 0.40673(13) 0.0432(5) Uani 1 1 d . . . . .
C8 C 0.23675(11) 0.8160(3) 0.31122(15) 0.0443(6) Uani 1 1 d . . . . .
H8 H 0.263939 0.757811 0.306220 0.053 Uiso 1 1 calc R U . . .
O2 O 0.18781(8) 0.46758(19) 0.27190(11) 0.0485(4) Uani 1 1 d . . . . .
N2 N -0.00611(8) 0.2192(2) 0.50680(12) 0.0408(5) Uani 1 1 d . . . . .
C11 C 0.21196(10) 0.5516(3) 0.33864(15) 0.0377(5) Uani 1 1 d . . . . .
C15 C 0.01940(10) 0.2901(3) 0.47488(14) 0.0341(5) Uani 1 1 d . . . . .
C2 C 0.08338(10) 0.8291(3) 0.35349(15) 0.0456(6) Uani 1 1 d . . . . .
H2 H 0.058011 0.775394 0.363102 0.055 Uiso 1 1 calc R U . . .
C14 C -0.02058(10) 0.3627(3) 0.38798(14) 0.0393(5) Uani 1 1 d . . . . .
H14 H -0.067084 0.364928 0.349724 0.047 Uiso 1 1 calc R U . . .
C7 C 0.23196(13) 0.9851(3) 0.30138(17) 0.0528(7) Uani 1 1 d . . . . .
H7 H 0.256300 1.040792 0.290547 0.063 Uiso 1 1 calc R U . . .
C16 C 0.08775(10) 0.2947(3) 0.52614(14) 0.0420(6) Uani 1 1 d . . . . .
H16 H 0.117908 0.249370 0.585899 0.050 Uiso 1 1 calc R U . . .
C4 C 0.11539(11) 1.0788(3) 0.33023(15) 0.0494(6) Uani 1 1 d . . . . .
H4 H 0.112463 1.193780 0.324079 0.059 Uiso 1 1 calc R U . . .
C13 C 0.00763(11) 0.4299(3) 0.35865(15) 0.0429(6) Uani 1 1 d . . . . .
H13 H -0.020908 0.477892 0.299524 0.052 Uiso 1 1 calc R U . . .
C3 C 0.08014(11) 0.9993(3) 0.34467(16) 0.0517(7) Uani 1 1 d . . . . .
H3 H 0.052866 1.059300 0.348896 0.062 Uiso 1 1 calc R U . . .
C17 C 0.11042(11) 0.3647(3) 0.48939(16) 0.0451(6) Uani 1 1 d . . . . .
H17 H 0.156659 0.364260 0.525343 0.054 Uiso 1 1 calc R U . . .
C6 C 0.19276(12) 1.0703(3) 0.30719(15) 0.0486(6) Uani 1 1 d . . . . .
H6 H 0.189673 1.185009 0.299611 0.058 Uiso 1 1 calc R U . . .
C18 C 0.03638(12) 0.1629(3) 0.60069(15) 0.0522(7) Uani 1 1 d . . . . .
H18A H 0.072978 0.100133 0.616104 0.078 Uiso 1 1 calc R U . . .
H18B H 0.011024 0.093881 0.607601 0.078 Uiso 1 1 calc R U . . .
H18C H 0.053842 0.256668 0.641785 0.078 Uiso 1 1 calc R U . . .
C19 C -0.07653(10) 0.2276(3) 0.45433(16) 0.0522(7) Uani 1 1 d . . . . .
H19A H -0.088927 0.340483 0.452186 0.078 Uiso 1 1 calc R U . . .
H19B H -0.086966 0.159456 0.483531 0.078 Uiso 1 1 calc R U . . .
H19C H -0.101071 0.188603 0.391961 0.078 Uiso 1 1 calc R U . . .
C12 C 0.25829(12) 0.4852(3) 0.43375(17) 0.0580(7) Uani 1 1 d . . . . .
H12A H 0.246272 0.372471 0.432805 0.087 Uiso 1 1 calc R U . . .
H12B H 0.255601 0.550957 0.472239 0.087 Uiso 1 1 calc R U . . .
H12C H 0.303401 0.488439 0.458601 0.087 Uiso 1 1 calc R U . . .
H1 H 0.1044(13) 0.529(4) 0.375(2) 0.091(9) 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
O1 C1 1.356(3) . ?
O1 H1 1.03(3) . ?
C10 C9 1.422(3) . ?
C10 C5 1.425(3) . ?
C10 C1 1.430(3) . ?
C9 C8 1.377(3) . ?
C9 C11 1.501(3) . ?
C1 C2 1.367(3) . ?
C5 C4 1.411(3) . ?
C5 C6 1.413(3) . ?
N1 C13 1.337(3) . ?
N1 C17 1.335(3) . ?
C8 C7 1.398(3) . ?
C8 H8 0.9500 . ?
O2 C11 1.218(2) . ?
N2 C15 1.358(2) . ?
N2 C18 1.451(3) . ?
N2 C19 1.456(3) . ?
C11 C12 1.494(3) . ?
C15 C14 1.405(3) . ?
C15 C16 1.411(3) . ?
C2 C3 1.406(3) . ?
C2 H2 0.9500 . ?
C14 C13 1.366(3) . ?
C14 H14 0.9500 . ?
C7 C6 1.357(3) . ?
C7 H7 0.9500 . ?
C16 C17 1.369(3) . ?
C16 H16 0.9500 . ?
C4 C3 1.354(3) . ?
C4 H4 0.9500 . ?
C13 H13 0.9500 . ?
C3 H3 0.9500 . ?
C17 H17 0.9500 . ?
C6 H6 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C1 O1 H1 111.6(17) . . ?
C9 C10 C5 119.35(19) . . ?
C9 C10 C1 122.5(2) . . ?
C5 C10 C1 118.14(19) . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 C11 116.57(19) . . ?
C10 C9 C11 123.85(18) . . ?
O1 C1 C2 123.7(2) . . ?
O1 C1 C10 116.21(18) . . ?
C2 C1 C10 120.1(2) . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 C10 119.7(2) . . ?
C6 C5 C10 118.4(2) . . ?
C13 N1 C17 115.29(19) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C15 N2 C18 120.99(17) . . ?
C15 N2 C19 120.48(18) . . ?
C18 N2 C19 117.35(17) . . ?
O2 C11 C12 122.6(2) . . ?
O2 C11 C9 119.7(2) . . ?
C12 C11 C9 117.3(2) . . ?
N2 C15 C14 122.23(18) . . ?
N2 C15 C16 122.43(19) . . ?
C14 C15 C16 115.34(19) . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C13 C14 125.0(2) . . ?
N1 C13 H13 117.5 . . ?
C14 C13 H13 117.5 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
N1 C17 C16 124.8(2) . . ?
N1 C17 H17 117.6 . . ?
C16 C17 H17 117.6 . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C5 C10 C9 C8 -0.1(3) . . . . ?
C1 C10 C9 C8 177.28(18) . . . . ?
C5 C10 C9 C11 179.61(19) . . . . ?
C1 C10 C9 C11 -3.0(3) . . . . ?
C9 C10 C1 O1 -0.5(3) . . . . ?
C5 C10 C1 O1 176.85(18) . . . . ?
C9 C10 C1 C2 -179.29(19) . . . . ?
C5 C10 C1 C2 -1.9(3) . . . . ?
C9 C10 C5 C4 179.51(18) . . . . ?
C1 C10 C5 C4 2.0(3) . . . . ?
C9 C10 C5 C6 0.0(3) . . . . ?
C1 C10 C5 C6 -177.45(18) . . . . ?
C10 C9 C8 C7 0.5(3) . . . . ?
C11 C9 C8 C7 -179.3(2) . . . . ?
C8 C9 C11 O2 -71.7(3) . . . . ?
C10 C9 C11 O2 108.6(2) . . . . ?
C8 C9 C11 C12 100.5(2) . . . . ?
C10 C9 C11 C12 -79.2(3) . . . . ?
C18 N2 C15 C14 -172.4(2) . . . . ?
C19 N2 C15 C14 -5.1(3) . . . . ?
C18 N2 C15 C16 8.3(3) . . . . ?
C19 N2 C15 C16 175.6(2) . . . . ?
O1 C1 C2 C3 -178.0(2) . . . . ?
C10 C1 C2 C3 0.7(3) . . . . ?
N2 C15 C14 C13 -178.9(2) . . . . ?
C16 C15 C14 C13 0.5(3) . . . . ?
C9 C8 C7 C6 -0.8(4) . . . . ?
N2 C15 C16 C17 178.5(2) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C6 C5 C4 C3 178.5(2) . . . . ?
C10 C5 C4 C3 -0.9(3) . . . . ?
C17 N1 C13 C14 -0.1(3) . . . . ?
C15 C14 C13 N1 0.0(4) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C13 N1 C17 C16 -0.4(3) . . . . ?
C15 C16 C17 N1 0.9(4) . . . . ?
C8 C7 C6 C5 0.7(4) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C10 C5 C6 C7 -0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 1.03(3) 1.60(3) 2.616(2) 173(3) .

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.036

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_JB060
_database_code_depnum_ccdc_archive 'CCDC 1849619'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_vrf_PLAT771_JB060               
;
PROBLEM:Suspect N-H Bond in CIF:   N1     --  H1      ..       1.51 Ang
RESPONSE: The hydrogen atom was located and refined. 
The hydrogen atom resides on hydroxyl with an O-H bond length
 of 1.07 Ang and hydrogen bond to N1 of 1.51 Ang. 
Although refined hydrogen atom positions from xray 
data are not very reliable, we note that the C-O bond length
 is inconsistent with oxygen being deprotonated. Of course we
could have fixed the O-H bond length, but chose not to do it.
;
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
"4-(dimethylamino)pyridine 1-(2'-t-butyl-8'-hydroxylnaphthalen-1'-yl)ethanonemolecular complex"
_chemical_name_common            ?
_chemical_melting_point          368
_chemical_formula_moiety         'C16 H18 O2, C7 H10 N2'
_chemical_formula_sum            'C23 H28 N2 O2'
_chemical_formula_weight         364.47


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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1265(11)
_cell_length_b                   25.804(3)
_cell_length_c                   7.9261(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.497(10)
_cell_angle_gamma                90
_cell_volume                     1995.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    2236
_cell_measurement_theta_min      3.1360
_cell_measurement_theta_max      26.3930

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.132
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            9885
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.099
_diffrn_reflns_theta_max         29.224
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4601
_reflns_number_gt                2813
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.0141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4601
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
O1 O 0.84784(15) 0.09847(6) 0.93335(17) 0.0377(4) Uani 1 1 d . . . . .
O2 O 0.56409(16) 0.07337(7) 0.72795(18) 0.0424(4) Uani 1 1 d . . . . .
C9 C 0.6660(2) 0.14940(8) 0.6465(2) 0.0262(5) Uani 1 1 d . . . . .
C10 C 0.8104(2) 0.16035(8) 0.7040(2) 0.0264(5) Uani 1 1 d . . . . .
C15 C 0.6052(2) 0.11685(10) 0.7654(2) 0.0320(5) Uani 1 1 d . . . . .
C6 C 0.7862(2) 0.21606(9) 0.4523(2) 0.0357(5) Uani 1 1 d . . . . .
H6 H 0.824551 0.238800 0.383845 0.043 Uiso 1 1 calc R U . . .
N2 N 1.25058(19) 0.01661(8) 1.7082(2) 0.0394(5) Uani 1 1 d . . . . .
C1 C 0.8995(2) 0.13679(9) 0.8558(2) 0.0291(5) Uani 1 1 d . . . . .
C5 C 0.8703(2) 0.19606(9) 0.6089(2) 0.0300(5) Uani 1 1 d . . . . .
N1 N 1.00735(19) 0.06173(8) 1.2182(2) 0.0391(5) Uani 1 1 d . . . . .
C19 C 1.1714(2) 0.03109(9) 1.5492(2) 0.0308(5) Uani 1 1 d . . . . .
C4 C 1.0093(2) 0.21032(9) 0.6716(3) 0.0362(5) Uani 1 1 d . . . . .
H4 H 1.048469 0.234053 0.607122 0.043 Uiso 1 1 calc R U . . .
C2 C 1.0324(2) 0.15304(9) 0.9150(2) 0.0347(5) Uani 1 1 d . . . . .
H2 H 1.088790 0.138785 1.020166 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5846(2) 0.17111(8) 0.4923(2) 0.0290(5) Uani 1 1 d . . . . .
C18 C 1.0802(2) 0.07303(9) 1.5284(2) 0.0326(5) Uani 1 1 d . . . . .
H18 H 1.071679 0.091964 1.627701 0.039 Uiso 1 1 calc R U . . .
C20 C 1.1757(2) 0.00508(9) 1.3954(3) 0.0348(5) Uani 1 1 d . . . . .
H20 H 1.235262 -0.023663 1.400402 0.042 Uiso 1 1 calc R U . . .
C11 C 0.4286(2) 0.16198(9) 0.4186(2) 0.0325(5) Uani 1 1 d . . . . .
C3 C 1.0871(2) 0.19015(10) 0.8242(3) 0.0370(6) Uani 1 1 d . . . . .
H3 H 1.179153 0.201319 0.869509 0.044 Uiso 1 1 calc R U . . .
C13 C 0.4033(2) 0.10846(10) 0.3325(3) 0.0394(6) Uani 1 1 d . . . . .
H13A H 0.304558 0.103038 0.284605 0.059 Uiso 1 1 calc R U . . .
H13B H 0.440534 0.081686 0.419953 0.059 Uiso 1 1 calc R U . . .
H13C H 0.448564 0.106404 0.237781 0.059 Uiso 1 1 calc R U . . .
C21 C 1.0937(2) 0.02139(10) 1.2385(3) 0.0381(6) Uani 1 1 d . . . . .
H21 H 1.098118 0.002896 1.136524 0.046 Uiso 1 1 calc R U . . .
C7 C 0.6517(2) 0.20371(9) 0.3967(3) 0.0358(6) Uani 1 1 d . . . . .
H7 H 0.599528 0.217518 0.288274 0.043 Uiso 1 1 calc R U . . .
C17 C 1.0038(2) 0.08650(10) 1.3651(3) 0.0378(6) Uani 1 1 d . . . . .
H17 H 0.944162 0.115410 1.355075 0.045 Uiso 1 1 calc R U . . .
C23 C 1.2467(3) 0.04456(11) 1.8653(3) 0.0509(7) Uani 1 1 d . . . . .
H23A H 1.286207 0.079135 1.863169 0.076 Uiso 1 1 calc R U . . .
H23B H 1.299673 0.025608 1.968382 0.076 Uiso 1 1 calc R U . . .
H23C H 1.151444 0.047841 1.870636 0.076 Uiso 1 1 calc R U . . .
C16 C 0.5915(2) 0.14349(10) 0.9301(2) 0.0445(6) Uani 1 1 d . . . . .
H16A H 0.510248 0.165812 0.901695 0.067 Uiso 1 1 calc R U . . .
H16B H 0.673230 0.164552 0.979381 0.067 Uiso 1 1 calc R U . . .
H16C H 0.582138 0.117338 1.015829 0.067 Uiso 1 1 calc R U . . .
C22 C 1.3498(3) -0.02460(11) 1.7235(3) 0.0520(7) Uani 1 1 d . . . . .
H22A H 1.303168 -0.056292 1.670913 0.078 Uiso 1 1 calc R U . . .
H22B H 1.395146 -0.030805 1.847423 0.078 Uiso 1 1 calc R U . . .
H22C H 1.418284 -0.014623 1.662502 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3489(2) 0.16603(11) 0.5579(3) 0.0437(6) Uani 1 1 d . . . . .
H12A H 0.375461 0.197860 0.625925 0.066 Uiso 1 1 calc R U . . .
H12B H 0.370034 0.135987 0.636096 0.066 Uiso 1 1 calc R U . . .
H12C H 0.250391 0.166831 0.500462 0.066 Uiso 1 1 calc R U . . .
C14 C 0.3640(2) 0.20237(11) 0.2793(3) 0.0485(7) Uani 1 1 d . . . . .
H14A H 0.400690 0.198107 0.177635 0.073 Uiso 1 1 calc R U . . .
H14B H 0.385486 0.237224 0.328002 0.073 Uiso 1 1 calc R U . . .
H14C H 0.264336 0.197606 0.243259 0.073 Uiso 1 1 calc R U . . .
H1 H 0.918(3) 0.0847(11) 1.051(3) 0.080(9) 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
O1 C1 1.342(2) . ?
O1 H1 1.07(3) . ?
O2 C15 1.206(3) . ?
C9 C8 1.396(3) . ?
C9 C10 1.438(3) . ?
C9 C15 1.511(3) . ?
C10 C5 1.425(3) . ?
C10 C1 1.432(3) . ?
C15 C16 1.514(3) . ?
C6 C7 1.353(3) . ?
C6 C5 1.402(3) . ?
C6 H6 0.9500 . ?
N2 C19 1.353(3) . ?
N2 C22 1.445(3) . ?
N2 C23 1.448(3) . ?
C1 C2 1.366(3) . ?
C5 C4 1.411(3) . ?
N1 C17 1.337(3) . ?
N1 C21 1.341(3) . ?
N1 H1 1.51(3) . ?
C19 C20 1.403(3) . ?
C19 C18 1.404(3) . ?
C4 C3 1.359(3) . ?
C4 H4 0.9500 . ?
C2 C3 1.398(3) . ?
C2 H2 0.9500 . ?
C8 C7 1.420(3) . ?
C8 C11 1.549(3) . ?
C18 C17 1.363(3) . ?
C18 H18 0.9500 . ?
C20 C21 1.364(3) . ?
C20 H20 0.9500 . ?
C11 C13 1.532(3) . ?
C11 C14 1.532(3) . ?
C11 C12 1.535(3) . ?
C3 H3 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 H21 0.9500 . ?
C7 H7 0.9500 . ?
C17 H17 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C1 O1 H1 113.3(15) . . ?
C8 C9 C10 120.73(18) . . ?
C8 C9 C15 121.71(18) . . ?
C10 C9 C15 117.42(17) . . ?
C5 C10 C1 117.18(18) . . ?
C5 C10 C9 119.96(17) . . ?
C1 C10 C9 122.85(18) . . ?
O2 C15 C9 122.35(18) . . ?
O2 C15 C16 121.97(19) . . ?
C9 C15 C16 115.6(2) . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C19 N2 C22 120.44(18) . . ?
C19 N2 C23 121.17(19) . . ?
C22 N2 C23 118.19(19) . . ?
O1 C1 C2 122.51(19) . . ?
O1 C1 C10 117.49(18) . . ?
C2 C1 C10 120.00(19) . . ?
C6 C5 C4 121.9(2) . . ?
C6 C5 C10 117.56(19) . . ?
C4 C5 C10 120.53(18) . . ?
C17 N1 C21 115.77(19) . . ?
C17 N1 H1 115.2(10) . . ?
C21 N1 H1 128.9(10) . . ?
N2 C19 C20 122.0(2) . . ?
N2 C19 C18 122.02(18) . . ?
C20 C19 C18 116.02(19) . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C1 C2 C3 121.51(19) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C9 C8 C7 116.75(19) . . ?
C9 C8 C11 124.95(18) . . ?
C7 C8 C11 118.30(18) . . ?
C17 C18 C19 119.80(19) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C13 C11 C14 107.68(18) . . ?
C13 C11 C12 108.93(19) . . ?
C14 C11 C12 105.44(19) . . ?
C13 C11 C8 109.74(18) . . ?
C14 C11 C8 111.38(19) . . ?
C12 C11 C8 113.44(16) . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C21 C20 124.6(2) . . ?
N1 C21 H21 117.7 . . ?
C20 C21 H21 117.7 . . ?
C6 C7 C8 123.30(19) . . ?
C6 C7 H7 118.4 . . ?
C8 C7 H7 118.3 . . ?
N1 C17 C18 124.4(2) . . ?
N1 C17 H17 117.8 . . ?
C18 C17 H17 117.8 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C8 C9 C10 C5 3.7(3) . . . . ?
C15 C9 C10 C5 -172.11(18) . . . . ?
C8 C9 C10 C1 -176.42(19) . . . . ?
C15 C9 C10 C1 7.8(3) . . . . ?
C8 C9 C15 O2 73.2(3) . . . . ?
C10 C9 C15 O2 -111.0(2) . . . . ?
C8 C9 C15 C16 -103.3(2) . . . . ?
C10 C9 C15 C16 72.4(2) . . . . ?
C5 C10 C1 O1 -171.87(17) . . . . ?
C9 C10 C1 O1 8.2(3) . . . . ?
C5 C10 C1 C2 7.2(3) . . . . ?
C9 C10 C1 C2 -172.69(19) . . . . ?
C7 C6 C5 C4 -177.4(2) . . . . ?
C7 C6 C5 C10 2.6(3) . . . . ?
C1 C10 C5 C6 174.90(19) . . . . ?
C9 C10 C5 C6 -5.2(3) . . . . ?
C1 C10 C5 C4 -5.1(3) . . . . ?
C9 C10 C5 C4 174.85(19) . . . . ?
C22 N2 C19 C20 4.1(3) . . . . ?
C23 N2 C19 C20 178.8(2) . . . . ?
C22 N2 C19 C18 -175.9(2) . . . . ?
C23 N2 C19 C18 -1.2(3) . . . . ?
C6 C5 C4 C3 179.8(2) . . . . ?
C10 C5 C4 C3 -0.2(3) . . . . ?
O1 C1 C2 C3 174.85(19) . . . . ?
C10 C1 C2 C3 -4.2(3) . . . . ?
C10 C9 C8 C7 0.5(3) . . . . ?
C15 C9 C8 C7 176.07(19) . . . . ?
C10 C9 C8 C11 -179.93(18) . . . . ?
C15 C9 C8 C11 -4.3(3) . . . . ?
N2 C19 C18 C17 179.2(2) . . . . ?
C20 C19 C18 C17 -0.8(3) . . . . ?
N2 C19 C20 C21 -179.9(2) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C9 C8 C11 C13 -76.8(2) . . . . ?
C7 C8 C11 C13 102.8(2) . . . . ?
C9 C8 C11 C14 164.0(2) . . . . ?
C7 C8 C11 C14 -16.4(3) . . . . ?
C9 C8 C11 C12 45.3(3) . . . . ?
C7 C8 C11 C12 -135.2(2) . . . . ?
C5 C4 C3 C2 3.6(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C17 N1 C21 C20 -0.3(3) . . . . ?
C19 C20 C21 N1 0.5(3) . . . . ?
C5 C6 C7 C8 1.6(4) . . . . ?
C9 C8 C7 C6 -3.2(3) . . . . ?
C11 C8 C7 C6 177.2(2) . . . . ?
C21 N1 C17 C18 -0.5(3) . . . . ?
C19 C18 C17 N1 1.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 1.07(3) 1.51(3) 2.580(2) 175(3) .

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_JB148
_database_code_depnum_ccdc_archive 'CCDC 1849628'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ethyl (E)-2-cyano-3-(1-hydroxynaphthalen-8-yl)acrylate
;
_chemical_name_common            ?
_chemical_melting_point          468
_chemical_formula_moiety         'C16 H13 N O3'
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8607(7)
_cell_length_b                   8.0882(5)
_cell_length_c                   15.3629(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.510(5)
_cell_angle_gamma                90
_cell_volume                     1326.89(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2158
_cell_measurement_theta_min      3.5660
_cell_measurement_theta_max      28.6680

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.643
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.144
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7270
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.857
_diffrn_reflns_theta_max         29.200
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3097
_reflns_number_gt                2604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.5744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3097
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
O1 O 0.87530(10) 0.33354(16) 0.02857(8) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.54152(11) 0.46235(19) 0.23154(8) 0.0365(4) Uani 1 1 d . . . . .
O3 O 0.59473(10) 0.60269(16) 0.11734(7) 0.0260(3) Uani 1 1 d . . . . .
N1 N 0.80186(13) 0.3089(2) 0.36400(9) 0.0264(3) Uani 1 1 d . . . . .
C1 C 1.00129(15) 0.3210(2) 0.05647(10) 0.0200(3) Uani 1 1 d . . . . .
C2 C 1.07736(16) 0.2385(2) 0.00859(11) 0.0233(4) Uani 1 1 d . . . . .
H2 H 1.0424 0.1903 -0.0468 0.028 Uiso 1 1 calc R U . . .
C3 C 1.20641(16) 0.2249(2) 0.04118(12) 0.0259(4) Uani 1 1 d . . . . .
H3 H 1.2581 0.1687 0.0071 0.031 Uiso 1 1 calc R U . . .
C4 C 1.25847(16) 0.2912(2) 0.12091(11) 0.0241(4) Uani 1 1 d . . . . .
H4 H 1.3460 0.2809 0.1420 0.029 Uiso 1 1 calc R U . . .
C5 C 1.18269(15) 0.3755(2) 0.17261(10) 0.0199(3) Uani 1 1 d . . . . .
C6 C 1.23519(15) 0.4383(2) 0.25762(11) 0.0234(4) Uani 1 1 d . . . . .
H6 H 1.3229 0.4302 0.2784 0.028 Uiso 1 1 calc R U . . .
C7 C 1.16119(15) 0.5100(2) 0.30988(11) 0.0234(4) Uani 1 1 d . . . . .
H7 H 1.1973 0.5497 0.3670 0.028 Uiso 1 1 calc R U . . .
C8 C 1.03184(15) 0.5250(2) 0.27921(10) 0.0212(4) Uani 1 1 d . . . . .
H8 H 0.9812 0.5732 0.3167 0.025 Uiso 1 1 calc R U . . .
C9 C 0.97626(14) 0.4713(2) 0.19581(10) 0.0182(3) Uani 1 1 d . . . . .
C10 C 1.05169(14) 0.3938(2) 0.14012(10) 0.0182(3) Uani 1 1 d . . . . .
C11 C 0.84132(14) 0.5028(2) 0.16717(10) 0.0191(3) Uani 1 1 d . . . . .
H11 H 0.8143 0.5502 0.1103 0.023 Uiso 1 1 calc R U . . .
C12 C 0.75404(15) 0.4687(2) 0.21626(10) 0.0197(3) Uani 1 1 d . . . . .
C13 C 0.78262(15) 0.3803(2) 0.29873(10) 0.0206(3) Uani 1 1 d . . . . .
C14 C 0.61855(15) 0.5095(2) 0.19004(11) 0.0232(4) Uani 1 1 d . . . . .
C15 C 0.46361(17) 0.6525(3) 0.09030(13) 0.0347(5) Uani 1 1 d . . . . .
H15A H 0.4307 0.6962 0.1417 0.042 Uiso 1 1 calc R U . . .
H15B H 0.4120 0.5564 0.0662 0.042 Uiso 1 1 calc R U . . .
C16 C 0.4590(2) 0.7817(3) 0.02183(16) 0.0483(6) Uani 1 1 d . . . . .
H16A H 0.5080 0.8777 0.0470 0.072 Uiso 1 1 calc R U . . .
H16B H 0.3719 0.8151 0.0009 0.072 Uiso 1 1 calc R U . . .
H16C H 0.4941 0.7381 -0.0279 0.072 Uiso 1 1 calc R U . . .
H1 H 0.855(2) 0.291(3) -0.0250(16) 0.050(7) 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
O1 C1 1.3610(18) . ?
O2 C14 1.203(2) . ?
O3 C14 1.333(2) . ?
O3 C15 1.465(2) . ?
N1 C13 1.143(2) . ?
C1 C2 1.375(2) . ?
C1 C10 1.429(2) . ?
C2 C3 1.404(2) . ?
C3 C4 1.362(2) . ?
C4 C5 1.418(2) . ?
C5 C6 1.420(2) . ?
C5 C10 1.427(2) . ?
C6 C7 1.365(2) . ?
C7 C8 1.403(2) . ?
C8 C9 1.383(2) . ?
C9 C10 1.433(2) . ?
C9 C11 1.473(2) . ?
C11 C12 1.343(2) . ?
C12 C13 1.439(2) . ?
C12 C14 1.490(2) . ?
C15 C16 1.477(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
C14 O3 C15 115.03(13) . . ?
O1 C1 C2 122.36(15) . . ?
O1 C1 C10 116.80(14) . . ?
C2 C1 C10 120.81(15) . . ?
C1 C2 C3 120.35(15) . . ?
C4 C3 C2 120.90(16) . . ?
C3 C4 C5 120.32(15) . . ?
C4 C5 C6 120.67(15) . . ?
C4 C5 C10 119.82(15) . . ?
C6 C5 C10 119.48(14) . . ?
C7 C6 C5 120.80(15) . . ?
C6 C7 C8 120.02(15) . . ?
C9 C8 C7 121.68(15) . . ?
C8 C9 C10 119.35(14) . . ?
C8 C9 C11 117.70(14) . . ?
C10 C9 C11 122.91(14) . . ?
C5 C10 C1 117.77(14) . . ?
C5 C10 C9 118.61(14) . . ?
C1 C10 C9 123.40(14) . . ?
C12 C11 C9 124.22(14) . . ?
C11 C12 C13 122.37(15) . . ?
C11 C12 C14 124.48(15) . . ?
C13 C12 C14 113.07(14) . . ?
N1 C13 C12 178.09(17) . . ?
O2 C14 O3 125.16(15) . . ?
O2 C14 C12 122.33(15) . . ?
O3 C14 C12 112.51(13) . . ?
O3 C15 C16 107.54(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.89(2) 1.87(3) 2.7585(18) 174(2) 4_565


_refine_diff_density_max         0.273
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_JB147
_database_code_depnum_ccdc_archive 'CCDC 1849629'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            
;
2-((8'-hydroxynaphthalen-1'-yl)methylene)malononitrile
;
_chemical_melting_point          419
_chemical_formula_moiety         'C14 H8 N2 O'
_chemical_formula_sum            'C14 H8 N2 O'
_chemical_formula_weight         220.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9169(5)
_cell_length_b                   7.4879(2)
_cell_length_c                   15.8768(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.096(5)
_cell_angle_gamma                90
_cell_volume                     1120.64(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    1690
_cell_measurement_theta_min      3.8310
_cell_measurement_theta_max      27.6950

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            4740
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.037
_diffrn_reflns_theta_max         29.106
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.821
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.821
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2465
_reflns_number_gt                1936
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.1418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2465
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
O1 O 0.09820(13) 0.28934(16) 0.07158(7) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.49031(17) 0.5692(2) 0.30875(10) 0.0463(4) Uani 1 1 d . . . . .
H1 H 0.125(2) 0.247(3) 0.0278(14) 0.057(6) Uiso 1 1 d . . . . .
N2 N 0.19316(16) 0.33752(19) 0.43195(8) 0.0348(4) Uani 1 1 d . . . . .
C1 C -0.04584(19) 0.2998(2) 0.04781(9) 0.0273(4) Uani 1 1 d . . . . .
C2 C -0.1323(2) 0.2308(2) -0.03031(10) 0.0346(4) Uani 1 1 d . . . . .
H2 H -0.091584 0.177697 -0.071091 0.042 Uiso 1 1 calc R U . . .
C3 C -0.2798(2) 0.2381(2) -0.05044(11) 0.0406(5) Uani 1 1 d . . . . .
H3 H -0.338437 0.193561 -0.105731 0.049 Uiso 1 1 calc R U . . .
C4 C -0.3405(2) 0.3082(2) 0.00824(11) 0.0375(4) Uani 1 1 d . . . . .
H4 H -0.440879 0.309876 -0.005816 0.045 Uiso 1 1 calc R U . . .
C5 C -0.25447(18) 0.3788(2) 0.09035(10) 0.0291(4) Uani 1 1 d . . . . .
C6 C -0.31559(18) 0.4445(2) 0.15424(11) 0.0316(4) Uani 1 1 d . . . . .
H6 H -0.415861 0.445454 0.140806 0.038 Uiso 1 1 calc R U . . .
C7 C -0.23300(18) 0.5061(2) 0.23439(10) 0.0299(4) Uani 1 1 d . . . . .
H7 H -0.275472 0.544793 0.277247 0.036 Uiso 1 1 calc R U . . .
C8 C -0.08558(17) 0.5123(2) 0.25350(9) 0.0260(4) Uani 1 1 d . . . . .
H8 H -0.029285 0.557007 0.309350 0.031 Uiso 1 1 calc R U . . .
C9 C -0.01939(17) 0.45512(19) 0.19338(9) 0.0227(3) Uani 1 1 d . . . . .
C10 C -0.10450(17) 0.3804(2) 0.11003(9) 0.0247(4) Uani 1 1 d . . . . .
C11 C 0.13178(17) 0.48855(19) 0.21262(9) 0.0236(3) Uani 1 1 d . . . . .
H11 H 0.162409 0.525541 0.164291 0.028 Uiso 1 1 calc R U . . .
C12 C 0.23310(17) 0.4725(2) 0.29199(9) 0.0238(3) Uani 1 1 d . . . . .
C13 C 0.37682(19) 0.5252(2) 0.30185(10) 0.0299(4) Uani 1 1 d . . . . .
C14 C 0.20899(17) 0.3986(2) 0.36972(10) 0.0260(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
O1 C1 1.362(2) . ?
O1 H1 0.88(2) . ?
N1 C13 1.145(2) . ?
N2 C14 1.1427(19) . ?
C1 C2 1.371(2) . ?
C1 C10 1.427(2) . ?
C2 C3 1.399(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(2) . ?
C4 H4 0.9500 . ?
C5 C10 1.422(2) . ?
C5 C6 1.421(2) . ?
C6 C7 1.362(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.443(2) . ?
C9 C11 1.456(2) . ?
C11 C12 1.351(2) . ?
C11 H11 0.9500 . ?
C12 C14 1.439(2) . ?
C12 C13 1.440(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
C1 O1 H1 110.5(14) . . ?
O1 C1 C2 122.43(15) . . ?
O1 C1 C10 116.79(14) . . ?
C2 C1 C10 120.73(16) . . ?
C1 C2 C3 120.52(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.80(16) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.30(17) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C10 119.61(15) . . ?
C4 C5 C6 121.08(16) . . ?
C10 C5 C6 119.30(14) . . ?
C7 C6 C5 121.19(16) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.91(14) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 121.87(15) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 119.01(15) . . ?
C8 C9 C11 118.71(13) . . ?
C10 C9 C11 122.00(13) . . ?
C5 C10 C1 117.92(14) . . ?
C5 C10 C9 118.59(14) . . ?
C1 C10 C9 123.42(15) . . ?
C12 C11 C9 126.84(13) . . ?
C12 C11 H11 116.6 . . ?
C9 C11 H11 116.6 . . ?
C11 C12 C14 124.10(15) . . ?
C11 C12 C13 120.09(13) . . ?
C14 C12 C13 115.78(14) . . ?
N1 C13 C12 178.93(18) . . ?
N2 C14 C12 178.20(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 177.38(15) . . . . ?
C10 C1 C2 C3 0.0(2) . . . . ?
C1 C2 C3 C4 -2.2(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C10 1.7(2) . . . . ?
C3 C4 C5 C6 -176.87(15) . . . . ?
C4 C5 C6 C7 177.50(15) . . . . ?
C10 C5 C6 C7 -1.1(2) . . . . ?
C5 C6 C7 C8 2.7(2) . . . . ?
C6 C7 C8 C9 -0.8(2) . . . . ?
C7 C8 C9 C10 -2.5(2) . . . . ?
C7 C8 C9 C11 171.48(14) . . . . ?
C4 C5 C10 C1 -3.8(2) . . . . ?
C6 C5 C10 C1 174.79(13) . . . . ?
C4 C5 C10 C9 179.14(14) . . . . ?
C6 C5 C10 C9 -2.3(2) . . . . ?
O1 C1 C10 C5 -174.57(13) . . . . ?
C2 C1 C10 C5 3.0(2) . . . . ?
O1 C1 C10 C9 2.4(2) . . . . ?
C2 C1 C10 C9 179.93(14) . . . . ?
C8 C9 C10 C5 4.0(2) . . . . ?
C11 C9 C10 C5 -169.78(14) . . . . ?
C8 C9 C10 C1 -172.87(14) . . . . ?
C11 C9 C10 C1 13.3(2) . . . . ?
C8 C9 C11 C12 41.1(2) . . . . ?
C10 C9 C11 C12 -145.09(15) . . . . ?
C9 C11 C12 C14 7.5(3) . . . . ?
C9 C11 C12 C13 -174.71(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.88(2) 1.95(2) 2.8286(18) 177(2) 4_565

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
####################################################################### 
# 
# 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_JB030
_database_code_depnum_ccdc_archive 'CCDC 1849618'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_vrf_PLAT230_JB030               
;
PROBLEM: Hirshfeld Test Diff for    C14    --  C15     ..        7.5 s.u.
RESPONSE: C15 is a terminal methyl group and likely to have significant motion.
;
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
"4-(dimethylamino) pyridine 1-(8'-hydroxynaphthalen-1'-yl)-2-methylbutan-1-onemolecular complex"
_chemical_name_common            ?
_chemical_melting_point          357
_chemical_formula_moiety         'C15 H16 O2, C7 H10 N2'
_chemical_formula_sum            'C22 H26 N2 O2'
_chemical_formula_weight         350.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4313(5)
_cell_length_b                   26.5593(11)
_cell_length_c                   9.5945(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.586(7)
_cell_angle_gamma                90
_cell_volume                     1953.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(10)
_cell_measurement_reflns_used    1752
_cell_measurement_theta_min      3.5170
_cell_measurement_theta_max      26.0740

_exptl_crystal_description       Needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.099
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            10094
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.068
_diffrn_reflns_theta_max         29.315
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4523
_reflns_number_gt                3146
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0736P)²+0.7797P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4523
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.1822
_refine_ls_wR_factor_gt          0.1639
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O1 O 0.7804(2) 0.05384(6) 0.75610(18) 0.0338(4) Uani 1 1 d . . . . .
O2 O 0.6374(2) 0.16523(6) 0.7903(2) 0.0392(4) Uani 1 1 d . . . . .
N2 N 0.3373(3) 0.03887(7) 0.2706(2) 0.0365(5) Uani 1 1 d . . . . .
C9 C 0.9181(3) 0.15123(8) 0.7992(2) 0.0286(5) Uani 1 1 d . . . . .
C11 C 0.7786(3) 0.14472(8) 0.8570(3) 0.0293(5) Uani 1 1 d . . . . .
C10 C 0.9954(3) 0.11001(8) 0.7542(2) 0.0285(5) Uani 1 1 d . . . . .
N1 N 0.4997(3) 0.18861(7) 0.2850(2) 0.0389(5) Uani 1 1 d . . . . .
C18 C 0.4475(3) 0.14014(8) 0.2800(3) 0.0306(5) Uani 1 1 d . . . . .
C17 C 0.3350(3) 0.11683(9) 0.1430(3) 0.0312(5) Uani 1 1 d . . . . .
H17 H 0.292434 0.135182 0.049513 0.037 Uiso 1 1 calc R U . . .
C1 C 0.9292(3) 0.05993(9) 0.7368(2) 0.0319(5) Uani 1 1 d . . . . .
C16 C 0.2869(3) 0.06773(9) 0.1441(3) 0.0353(5) Uani 1 1 d . . . . .
H16 H 0.212849 0.052950 0.048970 0.042 Uiso 1 1 calc R U . . .
C5 C 1.1429(3) 0.11955(10) 0.7210(2) 0.0359(6) Uani 1 1 d . . . . .
C21 C 0.4450(4) 0.21788(9) 0.1448(3) 0.0401(6) Uani 1 1 d . . . . .
H21A H 0.486937 0.201634 0.074756 0.060 Uiso 1 1 calc R U . . .
H21B H 0.493842 0.251904 0.169075 0.060 Uiso 1 1 calc R U . . .
H21C H 0.317423 0.219848 0.096028 0.060 Uiso 1 1 calc R U . . .
C20 C 0.4434(3) 0.06169(9) 0.4021(3) 0.0382(6) Uani 1 1 d . . . . .
H20 H 0.479635 0.042745 0.494151 0.046 Uiso 1 1 calc R U . . .
C8 C 0.9790(3) 0.19914(9) 0.8001(3) 0.0382(6) Uani 1 1 d . . . . .
H8 H 0.923518 0.226534 0.825548 0.046 Uiso 1 1 calc R U . . .
C19 C 0.5023(3) 0.10991(9) 0.4124(3) 0.0361(6) Uani 1 1 d . . . . .
H19 H 0.580109 0.123109 0.508696 0.043 Uiso 1 1 calc R U . . .
C12 C 0.8288(3) 0.11952(9) 1.0111(3) 0.0322(5) Uani 1 1 d . . . . .
H12 H 0.921155 0.093915 1.025074 0.039 Uiso 1 1 calc R U . . .
C6 C 1.2029(3) 0.16968(11) 0.7279(3) 0.0435(6) Uani 1 1 d . . . . .
H6 H 1.301657 0.176285 0.707044 0.052 Uiso 1 1 calc R U . . .
C14 C 0.9071(4) 0.16058(10) 1.1338(3) 0.0435(6) Uani 1 1 d . . . . .
H14A H 0.998231 0.178888 1.114457 0.052 Uiso 1 1 calc R U . . .
H14B H 0.814532 0.185017 1.124437 0.052 Uiso 1 1 calc R U . . .
C2 C 1.0137(4) 0.02122(10) 0.7003(3) 0.0452(6) Uani 1 1 d . . . . .
H2 H 0.970449 -0.012208 0.691560 0.054 Uiso 1 1 calc R U . . .
C7 C 1.1218(3) 0.20859(10) 0.7641(3) 0.0429(6) Uani 1 1 d . . . . .
H7 H 1.161619 0.242100 0.764993 0.051 Uiso 1 1 calc R U . . .
C22 C 0.6386(4) 0.20865(10) 0.4230(3) 0.0454(7) Uani 1 1 d . . . . .
H22A H 0.610548 0.202647 0.511004 0.068 Uiso 1 1 calc R U . . .
H22B H 0.650093 0.244920 0.410881 0.068 Uiso 1 1 calc R U . . .
H22C H 0.748680 0.191867 0.440072 0.068 Uiso 1 1 calc R U . . .
C4 C 1.2266(4) 0.07904(12) 0.6833(3) 0.0499(7) Uani 1 1 d . . . . .
H4 H 1.326084 0.085098 0.663152 0.060 Uiso 1 1 calc R U . . .
C13 C 0.6736(4) 0.09290(11) 1.0214(3) 0.0495(7) Uani 1 1 d . . . . .
H13A H 0.579483 0.117215 1.002654 0.074 Uiso 1 1 calc R U . . .
H13B H 0.709476 0.078310 1.123890 0.074 Uiso 1 1 calc R U . . .
H13C H 0.632260 0.066083 0.944436 0.074 Uiso 1 1 calc R U . . .
C3 C 1.1645(4) 0.03122(12) 0.6761(3) 0.0534(8) Uani 1 1 d . . . . .
H3 H 1.224023 0.004113 0.654167 0.064 Uiso 1 1 calc R U . . .
C15 C 0.9869(5) 0.13973(13) 1.2970(3) 0.0682(9) Uani 1 1 d . . . . .
H15A H 0.895857 0.123388 1.319354 0.102 Uiso 1 1 calc R U . . .
H15B H 1.038578 0.167352 1.369635 0.102 Uiso 1 1 calc R U . . .
H15C H 1.077487 0.115100 1.306834 0.102 Uiso 1 1 calc R U . . .
H1 H 0.745(4) 0.0200(11) 0.745(3) 0.053(8) 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
O1 C1 1.352(3) . ?
O1 H1 0.94(3) . ?
O2 C11 1.221(3) . ?
N2 C16 1.346(3) . ?
N2 C20 1.349(3) . ?
C9 C8 1.371(3) . ?
C9 C10 1.430(3) . ?
C9 C11 1.505(3) . ?
C11 C12 1.514(3) . ?
C10 C1 1.425(3) . ?
C10 C5 1.429(3) . ?
N1 C18 1.355(3) . ?
N1 C21 1.452(3) . ?
N1 C22 1.455(3) . ?
C18 C17 1.405(3) . ?
C18 C19 1.408(3) . ?
C17 C16 1.367(3) . ?
C17 H17 0.9500 . ?
C1 C2 1.376(3) . ?
C16 H16 0.9500 . ?
C5 C4 1.413(4) . ?
C5 C6 1.416(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C20 C19 1.362(3) . ?
C20 H20 0.9500 . ?
C8 C7 1.407(4) . ?
C8 H8 0.9500 . ?
C19 H19 0.9500 . ?
C12 C13 1.526(3) . ?
C12 C14 1.537(3) . ?
C12 H12 1.0000 . ?
C6 C7 1.361(4) . ?
C6 H6 0.9500 . ?
C14 C15 1.528(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C2 C3 1.410(4) . ?
C2 H2 0.9500 . ?
C7 H7 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C4 C3 1.364(4) . ?
C4 H4 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C3 H3 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C1 O1 H1 111.2(17) . . ?
C16 N2 C20 115.2(2) . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 C11 116.9(2) . . ?
C10 C9 C11 123.22(19) . . ?
O2 C11 C9 119.8(2) . . ?
O2 C11 C12 121.7(2) . . ?
C9 C11 C12 117.85(18) . . ?
C1 C10 C5 118.3(2) . . ?
C1 C10 C9 123.0(2) . . ?
C5 C10 C9 118.7(2) . . ?
C18 N1 C21 120.17(19) . . ?
C18 N1 C22 120.4(2) . . ?
C21 N1 C22 118.2(2) . . ?
N1 C18 C17 122.3(2) . . ?
N1 C18 C19 122.0(2) . . ?
C17 C18 C19 115.7(2) . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
O1 C1 C2 123.6(2) . . ?
O1 C1 C10 115.9(2) . . ?
C2 C1 C10 120.5(2) . . ?
N2 C16 C17 124.5(2) . . ?
N2 C16 H16 117.7 . . ?
C17 C16 H16 117.7 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 C10 119.7(2) . . ?
C6 C5 C10 118.9(2) . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C20 C19 124.8(2) . . ?
N2 C20 H20 117.6 . . ?
C19 C20 H20 117.6 . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C11 C12 C13 111.7(2) . . ?
C11 C12 C14 106.89(19) . . ?
C13 C12 C14 112.7(2) . . ?
C11 C12 H12 108.5 . . ?
C13 C12 H12 108.5 . . ?
C14 C12 H12 108.5 . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C15 C14 C12 113.2(2) . . ?
C15 C14 H14A 108.9 . . ?
C12 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C12 C14 H14B 108.9 . . ?
H14A C14 H14B 107.8 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C6 C7 C8 120.0(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C8 C9 C11 O2 62.7(3) . . . . ?
C10 C9 C11 O2 -121.4(2) . . . . ?
C8 C9 C11 C12 -107.8(2) . . . . ?
C10 C9 C11 C12 68.0(3) . . . . ?
C8 C9 C10 C1 -174.1(2) . . . . ?
C11 C9 C10 C1 10.2(3) . . . . ?
C8 C9 C10 C5 4.2(3) . . . . ?
C11 C9 C10 C5 -171.54(19) . . . . ?
C21 N1 C18 C17 -2.4(3) . . . . ?
C22 N1 C18 C17 -169.4(2) . . . . ?
C21 N1 C18 C19 177.8(2) . . . . ?
C22 N1 C18 C19 10.8(4) . . . . ?
N1 C18 C17 C16 179.7(2) . . . . ?
C19 C18 C17 C16 -0.5(3) . . . . ?
C5 C10 C1 O1 -174.22(18) . . . . ?
C9 C10 C1 O1 4.1(3) . . . . ?
C5 C10 C1 C2 4.9(3) . . . . ?
C9 C10 C1 C2 -176.8(2) . . . . ?
C20 N2 C16 C17 -0.5(3) . . . . ?
C18 C17 C16 N2 1.4(4) . . . . ?
C1 C10 C5 C4 -4.7(3) . . . . ?
C9 C10 C5 C4 177.0(2) . . . . ?
C1 C10 C5 C6 175.9(2) . . . . ?
C9 C10 C5 C6 -2.5(3) . . . . ?
C16 N2 C20 C19 -1.4(4) . . . . ?
C10 C9 C8 C7 -2.9(3) . . . . ?
C11 C9 C8 C7 173.1(2) . . . . ?
N2 C20 C19 C18 2.2(4) . . . . ?
N1 C18 C19 C20 178.7(2) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
O2 C11 C12 C13 37.4(3) . . . . ?
C9 C11 C12 C13 -152.3(2) . . . . ?
O2 C11 C12 C14 -86.3(3) . . . . ?
C9 C11 C12 C14 84.1(2) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
C10 C5 C6 C7 -0.6(3) . . . . ?
C11 C12 C14 C15 -172.2(2) . . . . ?
C13 C12 C14 C15 64.7(3) . . . . ?
O1 C1 C2 C3 177.4(2) . . . . ?
C10 C1 C2 C3 -1.6(4) . . . . ?
C5 C6 C7 C8 2.0(4) . . . . ?
C9 C8 C7 C6 -0.2(4) . . . . ?
C6 C5 C4 C3 -179.3(3) . . . . ?
C10 C5 C4 C3 1.2(4) . . . . ?
C5 C4 C3 C2 2.2(4) . . . . ?
C1 C2 C3 C4 -2.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.94(3) 1.69(3) 2.627(2) 173(3) 3_656

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.045

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_JB041
_database_code_depnum_ccdc_archive 'CCDC 1849630'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6

_chemical_name_systematic        
;
 5-((8'-hydroxynaphthalen-1'-yl)methylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
;
_chemical_name_common            ?
_chemical_melting_point          443
_chemical_formula_moiety         'C17 H14 O5'
_chemical_formula_sum            'C17 H14 O5'
_chemical_formula_weight         298.28

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3963(3)
_cell_length_b                   14.2452(4)
_cell_length_c                   13.5274(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.187(4)
_cell_angle_gamma                90
_cell_volume                     1375.49(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2354
_cell_measurement_theta_min      3.1970
_cell_measurement_theta_max      28.7220

_exptl_crystal_description       Plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7338
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         29.178
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3198
_reflns_number_gt                2640
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+0.5778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3198
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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
O4 O 0.03983(17) 0.09364(9) 0.58600(10) 0.0181(3) Uani 1 1 d . . . . .
O2 O 0.34771(17) 0.20612(9) 0.84395(10) 0.0185(3) Uani 1 1 d . . . . .
O5 O 0.32530(17) 0.15339(9) 0.68871(10) 0.0184(3) Uani 1 1 d . . . . .
O3 O -0.20192(17) 0.06346(10) 0.64820(11) 0.0228(3) Uani 1 1 d . . . . .
O1 O -0.26902(19) 0.19114(10) 0.88610(10) 0.0217(3) Uani 1 1 d . . . . .
C5 C 0.0655(2) 0.14001(13) 1.13305(15) 0.0167(4) Uani 1 1 d . . . . .
C10 C -0.0140(2) 0.14280(12) 1.02484(14) 0.0142(4) Uani 1 1 d . . . . .
C2 C -0.2983(3) 0.20813(13) 1.05686(15) 0.0193(4) Uani 1 1 d . . . . .
H2 H -0.422086 0.231573 1.031451 0.023 Uiso 1 1 calc R U . . .
C13 C 0.2602(2) 0.15914(13) 0.77236(14) 0.0153(4) Uani 1 1 d . . . . .
C1 C -0.1979(2) 0.18111(13) 0.98957(14) 0.0164(4) Uani 1 1 d . . . . .
C4 C -0.0408(3) 0.16930(13) 1.20078(15) 0.0196(4) Uani 1 1 d . . . . .
H4 H 0.012501 0.166593 1.272697 0.024 Uiso 1 1 calc R U . . .
C11 C 0.0090(2) 0.09587(13) 0.84845(15) 0.0166(4) Uani 1 1 d . . . . .
H11 H -0.116838 0.074186 0.831054 0.020 Uiso 1 1 calc R U . . .
C12 C 0.0819(2) 0.11063(13) 0.76813(15) 0.0162(4) Uani 1 1 d . . . . .
C6 C 0.2507(3) 0.10646(13) 1.17168(15) 0.0200(4) Uani 1 1 d . . . . .
H6 H 0.305692 0.106136 1.243500 0.024 Uiso 1 1 calc R U . . .
C14 C -0.0401(2) 0.08579(13) 0.66531(15) 0.0170(4) Uani 1 1 d . . . . .
C9 C 0.0945(2) 0.10819(12) 0.95865(15) 0.0161(4) Uani 1 1 d . . . . .
C16 C 0.2912(3) 0.12339(14) 0.51372(15) 0.0218(4) Uani 1 1 d . . . . .
H16A H 0.246363 0.187974 0.499381 0.033 Uiso 1 1 calc R U . . .
H16B H 0.232751 0.083231 0.455267 0.033 Uiso 1 1 calc R U . . .
H16C H 0.427628 0.121861 0.525212 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2732(3) 0.07478(13) 1.00108(15) 0.0194(4) Uani 1 1 d . . . . .
H8 H 0.344633 0.051470 0.957378 0.023 Uiso 1 1 calc R U . . .
C3 C -0.2196(3) 0.20138(13) 1.16303(15) 0.0209(4) Uani 1 1 d . . . . .
H3 H -0.291161 0.219276 1.208892 0.025 Uiso 1 1 calc R U . . .
C17 C 0.3078(3) -0.01052(14) 0.63767(15) 0.0202(4) Uani 1 1 d . . . . .
H17A H 0.444790 -0.012549 0.653386 0.030 Uiso 1 1 calc R U . . .
H17B H 0.254344 -0.053480 0.580952 0.030 Uiso 1 1 calc R U . . .
H17C H 0.267575 -0.029546 0.698223 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3513(3) 0.07455(14) 1.10711(15) 0.0211(4) Uani 1 1 d . . . . .
H7 H 0.475247 0.052018 1.134396 0.025 Uiso 1 1 calc R U . . .
C15 C 0.2406(2) 0.08839(13) 0.60744(14) 0.0163(4) Uani 1 1 d . . . . .
H1 H -0.393(3) 0.2024(17) 0.8727(18) 0.035(7) 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
O4 C14 1.359(2) . ?
O4 C15 1.439(2) . ?
O2 C13 1.215(2) . ?
O5 C13 1.343(2) . ?
O5 C15 1.448(2) . ?
O3 C14 1.201(2) . ?
O1 C1 1.368(2) . ?
O1 H1 0.90(2) . ?
C5 C6 1.415(3) . ?
C5 C4 1.417(3) . ?
C5 C10 1.428(3) . ?
C10 C1 1.427(2) . ?
C10 C9 1.437(3) . ?
C2 C1 1.372(3) . ?
C2 C3 1.405(3) . ?
C2 H2 0.9500 . ?
C13 C12 1.477(2) . ?
C4 C3 1.365(3) . ?
C4 H4 0.9500 . ?
C11 C12 1.350(3) . ?
C11 C9 1.469(3) . ?
C11 H11 0.9500 . ?
C12 C14 1.489(3) . ?
C6 C7 1.365(3) . ?
C6 H6 0.9500 . ?
C9 C8 1.380(3) . ?
C16 C15 1.498(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C8 C7 1.399(3) . ?
C8 H8 0.9500 . ?
C3 H3 0.9500 . ?
C17 C15 1.514(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C7 H7 0.9500 . ?

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 O4 C15 118.46(14) . . ?
C13 O5 C15 119.96(14) . . ?
C1 O1 H1 108.8(15) . . ?
C6 C5 C4 120.52(18) . . ?
C6 C5 C10 119.12(18) . . ?
C4 C5 C10 120.36(16) . . ?
C1 C10 C5 116.99(17) . . ?
C1 C10 C9 124.19(17) . . ?
C5 C10 C9 118.82(16) . . ?
C1 C2 C3 120.49(17) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C13 O5 118.13(16) . . ?
O2 C13 C12 124.92(18) . . ?
O5 C13 C12 116.89(15) . . ?
O1 C1 C2 121.31(16) . . ?
O1 C1 C10 117.36(17) . . ?
C2 C1 C10 121.32(17) . . ?
C3 C4 C5 120.23(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C12 C11 C9 129.91(17) . . ?
C12 C11 H11 115.0 . . ?
C9 C11 H11 115.0 . . ?
C11 C12 C13 125.64(17) . . ?
C11 C12 C14 116.27(16) . . ?
C13 C12 C14 117.66(17) . . ?
C7 C6 C5 120.89(18) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O3 C14 O4 119.19(17) . . ?
O3 C14 C12 124.94(18) . . ?
O4 C14 C12 115.80(15) . . ?
C8 C9 C10 119.30(17) . . ?
C8 C9 C11 119.42(17) . . ?
C10 C9 C11 120.73(16) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C8 C7 121.35(19) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C4 C3 C2 120.47(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C7 C8 120.48(17) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
O4 C15 O5 109.76(14) . . ?
O4 C15 C16 106.59(14) . . ?
O5 C15 C16 105.99(15) . . ?
O4 C15 C17 110.55(15) . . ?
O5 C15 C17 110.12(15) . . ?
C16 C15 C17 113.66(16) . . ?

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
C6 C5 C10 C1 -177.26(16) . . . . ?
C4 C5 C10 C1 3.6(3) . . . . ?
C6 C5 C10 C9 2.2(3) . . . . ?
C4 C5 C10 C9 -176.93(16) . . . . ?
C15 O5 C13 O2 171.62(16) . . . . ?
C15 O5 C13 C12 -10.9(2) . . . . ?
C3 C2 C1 O1 -177.00(17) . . . . ?
C3 C2 C1 C10 2.0(3) . . . . ?
C5 C10 C1 O1 174.79(16) . . . . ?
C9 C10 C1 O1 -4.7(3) . . . . ?
C5 C10 C1 C2 -4.3(3) . . . . ?
C9 C10 C1 C2 176.28(18) . . . . ?
C6 C5 C4 C3 -179.84(18) . . . . ?
C10 C5 C4 C3 -0.7(3) . . . . ?
C9 C11 C12 C13 -11.2(3) . . . . ?
C9 C11 C12 C14 176.58(18) . . . . ?
O2 C13 C12 C11 -13.6(3) . . . . ?
O5 C13 C12 C11 169.13(17) . . . . ?
O2 C13 C12 C14 158.51(17) . . . . ?
O5 C13 C12 C14 -18.7(2) . . . . ?
C4 C5 C6 C7 177.32(18) . . . . ?
C10 C5 C6 C7 -1.8(3) . . . . ?
C15 O4 C14 O3 -159.05(17) . . . . ?
C15 O4 C14 C12 23.7(2) . . . . ?
C11 C12 C14 O3 8.1(3) . . . . ?
C13 C12 C14 O3 -164.74(18) . . . . ?
C11 C12 C14 O4 -174.84(16) . . . . ?
C13 C12 C14 O4 12.3(2) . . . . ?
C1 C10 C9 C8 178.34(17) . . . . ?
C5 C10 C9 C8 -1.1(3) . . . . ?
C1 C10 C9 C11 -10.2(3) . . . . ?
C5 C10 C9 C11 170.39(17) . . . . ?
C12 C11 C9 C8 -45.6(3) . . . . ?
C12 C11 C9 C10 142.9(2) . . . . ?
C10 C9 C8 C7 -0.5(3) . . . . ?
C11 C9 C8 C7 -172.07(18) . . . . ?
C5 C4 C3 C2 -1.7(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C9 C8 C7 C6 0.9(3) . . . . ?
C14 O4 C15 O5 -51.4(2) . . . . ?
C14 O4 C15 C16 -165.71(15) . . . . ?
C14 O4 C15 C17 70.3(2) . . . . ?
C13 O5 C15 O4 44.6(2) . . . . ?
C13 O5 C15 C16 159.30(15) . . . . ?
C13 O5 C15 C17 -77.36(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.90(2) 1.85(2) 2.7495(18) 171(2) 1_455

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.050

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/acetone'
####################################################################### 
# 
# 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_JB065
_database_code_depnum_ccdc_archive 'CCDC 1849632'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
7a-hydroxy-9-phenyl-7a,8,9,10-tetrahydro-11H-benzo[f]naphtho[1,8-bc]oxepin-11-one
_chemical_name_common            ?
_chemical_melting_point          447
_chemical_formula_moiety         'C23 H18 O3'
_chemical_formula_sum            'C23 H18 O3'
_chemical_formula_weight         342.37

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                   6.9441(4)
_cell_length_b                   8.8146(4)
_cell_length_c                   14.8418(8)
_cell_angle_alpha                77.773(4)
_cell_angle_beta                 78.744(4)
_cell_angle_gamma                76.371(4)
_cell_volume                     852.70(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    2718
_cell_measurement_theta_min      3.3960
_cell_measurement_theta_max      28.4170

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.081
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            8298
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.842
_diffrn_reflns_theta_max         29.479
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3941
_reflns_number_gt                3040
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.2903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3941
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
O2 O 0.3168(2) 0.11928(16) 0.06195(10) 0.0280(3) Uani 1 1 d . . . . .
O1 O 0.1967(2) 0.38870(16) 0.06814(9) 0.0277(3) Uani 1 1 d . . . . .
O3 O -0.3105(2) 0.20005(19) -0.00013(12) 0.0414(4) Uani 1 1 d . . . . .
C15 C 0.1953(3) 0.1957(2) -0.13224(14) 0.0270(4) Uani 1 1 d . . . . .
H15 H 0.253486 0.084551 -0.104549 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2432(3) 0.3081(2) -0.07723(14) 0.0271(4) Uani 1 1 d . . . . .
H14A H 0.388265 0.309053 -0.091590 0.033 Uiso 1 1 calc R U . . .
H14B H 0.168628 0.417209 -0.096398 0.033 Uiso 1 1 calc R U . . .
C11 C -0.1146(3) 0.2044(2) 0.14244(15) 0.0315(5) Uani 1 1 d . . . . .
C10 C 0.1156(3) 0.2803(2) 0.23544(14) 0.0314(5) Uani 1 1 d . . . . .
C1 C 0.2342(3) 0.3588(2) 0.15874(14) 0.0285(5) Uani 1 1 d . . . . .
C17 C -0.1342(3) 0.2109(2) -0.01923(15) 0.0287(5) Uani 1 1 d . . . . .
C12 C -0.0230(3) 0.2244(2) 0.05357(14) 0.0259(4) Uani 1 1 d . . . . .
C18 C 0.2928(3) 0.2266(2) -0.23300(14) 0.0299(5) Uani 1 1 d . . . . .
C16 C -0.0321(3) 0.2140(2) -0.11851(14) 0.0299(5) Uani 1 1 d . . . . .
H16A H -0.088809 0.315663 -0.156359 0.036 Uiso 1 1 calc R U . . .
H16B H -0.063581 0.127732 -0.142705 0.036 Uiso 1 1 calc R U . . .
C9 C -0.0481(3) 0.2099(2) 0.22822(15) 0.0308(5) Uani 1 1 d . . . . .
C2 C 0.3853(3) 0.4238(3) 0.17171(16) 0.0348(5) Uani 1 1 d . . . . .
H2 H 0.466047 0.471215 0.118962 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1592(3) 0.2766(3) 0.32638(16) 0.0391(6) Uani 1 1 d . . . . .
C13 C 0.1858(3) 0.2559(2) 0.02660(13) 0.0243(4) Uani 1 1 d . . . . .
C19 C 0.1979(3) 0.3339(3) -0.30226(15) 0.0384(5) Uani 1 1 d . . . . .
H19 H 0.061801 0.384837 -0.287708 0.046 Uiso 1 1 calc R U . . .
C23 C 0.4912(3) 0.1523(3) -0.25767(16) 0.0394(5) Uani 1 1 d . . . . .
H23 H 0.559167 0.077844 -0.212061 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3117(4) 0.3493(3) 0.33693(17) 0.0450(6) Uani 1 1 d . . . . .
H4 H 0.337453 0.347944 0.397685 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4226(3) 0.4217(3) 0.26110(17) 0.0421(6) Uani 1 1 d . . . . .
H3 H 0.525007 0.470480 0.269010 0.050 Uiso 1 1 calc R U . . .
C8 C -0.1552(3) 0.1417(3) 0.30939(16) 0.0420(6) Uani 1 1 d . . . . .
H8 H -0.263994 0.096821 0.304940 0.050 Uiso 1 1 calc R U . . .
C6 C 0.0447(4) 0.2030(3) 0.40559(17) 0.0479(6) Uani 1 1 d . . . . .
H6 H 0.075239 0.199670 0.465734 0.058 Uiso 1 1 calc R U . . .
C7 C -0.1084(4) 0.1365(3) 0.39806(17) 0.0489(7) Uani 1 1 d . . . . .
H7 H -0.183028 0.087080 0.452343 0.059 Uiso 1 1 calc R U . . .
C22 C 0.5906(4) 0.1853(3) -0.34738(17) 0.0492(7) Uani 1 1 d . . . . .
H22 H 0.725951 0.133645 -0.362855 0.059 Uiso 1 1 calc R U . . .
C20 C 0.2986(4) 0.3671(3) -0.39156(16) 0.0469(6) Uani 1 1 d . . . . .
H20 H 0.231879 0.441980 -0.437449 0.056 Uiso 1 1 calc R U . . .
C21 C 0.4943(4) 0.2931(3) -0.41487(17) 0.0497(7) Uani 1 1 d . . . . .
H21 H 0.562735 0.315744 -0.476614 0.060 Uiso 1 1 calc R U . . .
H11 H -0.244(3) 0.181(2) 0.1523(14) 0.030(6) Uiso 1 1 d . . . . .
H2A H 0.431(4) 0.146(3) 0.0447(18) 0.055(8) 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
O2 C13 1.399(2) . ?
O2 H2A 0.86(3) . ?
O1 C1 1.378(2) . ?
O1 C13 1.457(2) . ?
O3 C17 1.223(2) . ?
C15 C18 1.513(3) . ?
C15 C16 1.526(3) . ?
C15 C14 1.537(3) . ?
C15 H15 1.0000 . ?
C14 C13 1.514(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C11 C12 1.342(3) . ?
C11 C9 1.450(3) . ?
C11 H11 0.95(2) . ?
C10 C1 1.422(3) . ?
C10 C5 1.432(3) . ?
C10 C9 1.448(3) . ?
C1 C2 1.370(3) . ?
C17 C12 1.484(3) . ?
C17 C16 1.503(3) . ?
C12 C13 1.502(3) . ?
C18 C23 1.393(3) . ?
C18 C19 1.394(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C9 C8 1.386(3) . ?
C2 C3 1.396(3) . ?
C2 H2 0.9500 . ?
C5 C4 1.408(4) . ?
C5 C6 1.411(3) . ?
C19 C20 1.379(3) . ?
C19 H19 0.9500 . ?
C23 C22 1.380(3) . ?
C23 H23 0.9500 . ?
C4 C3 1.362(3) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C8 C7 1.405(3) . ?
C8 H8 0.9500 . ?
C6 C7 1.361(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C22 C21 1.383(3) . ?
C22 H22 0.9500 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C13 O2 H2A 102.6(18) . . ?
C1 O1 C13 118.48(14) . . ?
C18 C15 C16 114.51(16) . . ?
C18 C15 C14 110.17(16) . . ?
C16 C15 C14 107.93(16) . . ?
C18 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
C14 C15 H15 108.0 . . ?
C13 C14 C15 110.65(16) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C12 C11 C9 131.0(2) . . ?
C12 C11 H11 116.0(13) . . ?
C9 C11 H11 113.0(13) . . ?
C1 C10 C5 116.6(2) . . ?
C1 C10 C9 124.96(19) . . ?
C5 C10 C9 118.4(2) . . ?
C2 C1 O1 114.66(19) . . ?
C2 C1 C10 121.30(19) . . ?
O1 C1 C10 123.77(18) . . ?
O3 C17 C12 120.90(19) . . ?
O3 C17 C16 118.93(19) . . ?
C12 C17 C16 120.15(17) . . ?
C11 C12 C17 117.55(18) . . ?
C11 C12 C13 122.56(19) . . ?
C17 C12 C13 119.88(17) . . ?
C23 C18 C19 117.7(2) . . ?
C23 C18 C15 119.01(18) . . ?
C19 C18 C15 123.18(19) . . ?
C17 C16 C15 114.90(17) . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C8 C9 C10 118.7(2) . . ?
C8 C9 C11 115.4(2) . . ?
C10 C9 C11 125.94(19) . . ?
C1 C2 C3 121.1(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 C10 120.4(2) . . ?
C6 C5 C10 119.4(2) . . ?
O2 C13 O1 110.01(14) . . ?
O2 C13 C12 107.55(15) . . ?
O1 C13 C12 108.64(15) . . ?
O2 C13 C14 112.29(16) . . ?
O1 C13 C14 104.71(15) . . ?
C12 C13 C14 113.57(16) . . ?
C20 C19 C18 121.0(2) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C9 C8 C7 122.2(2) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 119.5(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C21 C20 C19 120.7(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.2(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?

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
C18 C15 C14 C13 -167.75(16) . . . . ?
C16 C15 C14 C13 66.6(2) . . . . ?
C13 O1 C1 C2 129.99(18) . . . . ?
C13 O1 C1 C10 -55.9(2) . . . . ?
C5 C10 C1 C2 1.5(3) . . . . ?
C9 C10 C1 C2 179.28(19) . . . . ?
C5 C10 C1 O1 -172.25(17) . . . . ?
C9 C10 C1 O1 5.5(3) . . . . ?
C9 C11 C12 C17 180.0(2) . . . . ?
C9 C11 C12 C13 1.3(3) . . . . ?
O3 C17 C12 C11 8.2(3) . . . . ?
C16 C17 C12 C11 -173.23(18) . . . . ?
O3 C17 C12 C13 -173.14(18) . . . . ?
C16 C17 C12 C13 5.5(3) . . . . ?
C16 C15 C18 C23 -152.9(2) . . . . ?
C14 C15 C18 C23 85.3(2) . . . . ?
C16 C15 C18 C19 31.2(3) . . . . ?
C14 C15 C18 C19 -90.7(2) . . . . ?
O3 C17 C16 C15 -168.77(18) . . . . ?
C12 C17 C16 C15 12.6(3) . . . . ?
C18 C15 C16 C17 -170.13(17) . . . . ?
C14 C15 C16 C17 -47.0(2) . . . . ?
C1 C10 C9 C8 -177.88(19) . . . . ?
C5 C10 C9 C8 -0.2(3) . . . . ?
C1 C10 C9 C11 1.5(3) . . . . ?
C5 C10 C9 C11 179.25(19) . . . . ?
C12 C11 C9 C8 -162.8(2) . . . . ?
C12 C11 C9 C10 17.7(4) . . . . ?
O1 C1 C2 C3 171.41(18) . . . . ?
C10 C1 C2 C3 -2.9(3) . . . . ?
C1 C10 C5 C4 0.5(3) . . . . ?
C9 C10 C5 C4 -177.4(2) . . . . ?
C1 C10 C5 C6 178.91(19) . . . . ?
C9 C10 C5 C6 1.0(3) . . . . ?
C1 O1 C13 O2 -32.9(2) . . . . ?
C1 O1 C13 C12 84.61(19) . . . . ?
C1 O1 C13 C14 -153.73(16) . . . . ?
C11 C12 C13 O2 67.1(2) . . . . ?
C17 C12 C13 O2 -111.51(18) . . . . ?
C11 C12 C13 O1 -51.9(2) . . . . ?
C17 C12 C13 O1 129.45(17) . . . . ?
C11 C12 C13 C14 -167.98(18) . . . . ?
C17 C12 C13 C14 13.4(2) . . . . ?
C15 C14 C13 O2 72.8(2) . . . . ?
C15 C14 C13 O1 -167.88(14) . . . . ?
C15 C14 C13 C12 -49.5(2) . . . . ?
C23 C18 C19 C20 -1.2(3) . . . . ?
C15 C18 C19 C20 174.9(2) . . . . ?
C19 C18 C23 C22 0.7(3) . . . . ?
C15 C18 C23 C22 -175.5(2) . . . . ?
C6 C5 C4 C3 -179.6(2) . . . . ?
C10 C5 C4 C3 -1.2(3) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C10 C9 C8 C7 -1.0(3) . . . . ?
C11 C9 C8 C7 179.6(2) . . . . ?
C4 C5 C6 C7 177.6(2) . . . . ?
C10 C5 C6 C7 -0.8(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C9 C8 C7 C6 1.2(4) . . . . ?
C18 C23 C22 C21 -0.1(4) . . . . ?
C18 C19 C20 C21 1.1(4) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C23 C22 C21 C20 0.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O3 0.86(3) 1.92(3) 2.777(2) 177(3) 1_655

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.049




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
####################################################################### 
# 
# 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_JB155
_database_code_depnum_ccdc_archive 'CCDC 1849631'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_vrf_PLAT097_JB155               
;
PROBLEM:  Large Reported Max.  (Positive) Residual Density       1.01 eA-3 
RESPONSE: 9 peaks with electron density at 0.41 - 1.01 eA-3
 lying in the naphthalene planes of the
 two independant molecules, in a similar arrangement. This hints at a small
 degree of an alternative orientation of the naphthofuran ring.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        
;
3-hydroxy-2-(2'H-naphtho[1,8-bc]furan-2'yl)cyclohex-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          460
_chemical_formula_moiety         'C17 H14 O3'
_chemical_formula_sum            'C17 H14 O3'
_chemical_formula_weight         266.28

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.4588(5)
_cell_length_b                   9.4421(3)
_cell_length_c                   20.9855(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.122(4)
_cell_angle_gamma                90
_cell_volume                     2656.17(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4438
_cell_measurement_theta_min      3.7280
_cell_measurement_theta_max      28.4450

_exptl_crystal_description       Block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            15960
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.039
_diffrn_reflns_theta_max         29.190
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6253
_reflns_number_gt                4538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS-2016
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6253
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2046
_refine_ls_wR_factor_gt          0.1853
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_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
O1 O 0.02756(14) 0.69271(17) 0.48217(9) 0.0296(4) Uani 1 1 d . . . . .
O2 O 0.10623(12) 0.88804(16) 0.39056(9) 0.0239(4) Uani 1 1 d . . . . .
O3 O -0.22423(14) 0.86386(19) 0.43778(10) 0.0283(5) Uani 1 1 d . . . . .
O4 O 0.47122(13) 0.25621(17) 0.38311(9) 0.0273(4) Uani 1 1 d . . . . .
O5 O 0.60937(12) -0.00190(17) 0.42195(9) 0.0247(4) Uani 1 1 d . . . . .
O6 O 0.26781(13) 0.01137(17) 0.36831(9) 0.0250(4) Uani 1 1 d . . . . .
C1 C 0.09545(19) 0.5979(2) 0.46511(13) 0.0237(6) Uani 1 1 d . . . . .
C2 C 0.1786(2) 0.5450(2) 0.49858(14) 0.0283(6) Uani 1 1 d . . . . .
H2 H 0.197263 0.574892 0.541205 0.034 Uiso 1 1 calc R U . . .
C3 C 0.2356(2) 0.4461(3) 0.46880(16) 0.0378(7) Uani 1 1 d . . . . .
H3 H 0.293274 0.409083 0.492415 0.045 Uiso 1 1 calc R U . . .
C4 C 0.2136(2) 0.3995(3) 0.40807(16) 0.0360(7) Uani 1 1 d . . . . .
H4 H 0.254656 0.330475 0.390524 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1295(2) 0.4538(2) 0.37099(13) 0.0260(6) Uani 1 1 d . . . . .
C6 C 0.0927(3) 0.4209(3) 0.30673(16) 0.0432(8) Uani 1 1 d . . . . .
H6 H 0.126087 0.353192 0.282823 0.052 Uiso 1 1 calc R U . . .
C7 C 0.0065(3) 0.4897(3) 0.27916(14) 0.0390(8) Uani 1 1 d . . . . .
H7 H -0.017802 0.467728 0.236410 0.047 Uiso 1 1 calc R U . . .
C8 C -0.0447(2) 0.5909(3) 0.31381(14) 0.0354(7) Uani 1 1 d . . . . .
H8 H -0.102084 0.637144 0.293947 0.042 Uiso 1 1 calc R U . . .
C9 C -0.0124(2) 0.6218(2) 0.37469(13) 0.0272(6) Uani 1 1 d . . . . .
C10 C 0.07202(19) 0.5524(2) 0.40050(13) 0.0253(6) Uani 1 1 d . . . . .
C11 C -0.04927(19) 0.7143(2) 0.42530(13) 0.0248(6) Uani 1 1 d . . . . .
H11 H -0.114859 0.676641 0.436662 0.030 Uiso 1 1 calc R U . . .
C12 C -0.05953(18) 0.8705(2) 0.41362(12) 0.0198(5) Uani 1 1 d . . . . .
C13 C -0.14776(18) 0.9384(2) 0.42030(12) 0.0211(5) Uani 1 1 d . . . . .
C14 C -0.16159(19) 1.0947(2) 0.41145(13) 0.0244(6) Uani 1 1 d . . . . .
H14A H -0.156340 1.141086 0.453925 0.029 Uiso 1 1 calc R U . . .
H14B H -0.229389 1.113046 0.390781 0.029 Uiso 1 1 calc R U . . .
C15 C -0.08510(19) 1.1601(2) 0.37087(13) 0.0246(6) Uani 1 1 d . . . . .
H15A H -0.101623 1.134175 0.325441 0.030 Uiso 1 1 calc R U . . .
H15B H -0.087645 1.264536 0.374308 0.030 Uiso 1 1 calc R U . . .
C16 C 0.01960(18) 1.1086(2) 0.39268(12) 0.0211(5) Uani 1 1 d . . . . .
H16A H 0.066137 1.141527 0.361844 0.025 Uiso 1 1 calc R U . . .
H16B H 0.040957 1.151245 0.434791 0.025 Uiso 1 1 calc R U . . .
C17 C 0.02626(17) 0.9502(2) 0.39817(11) 0.0178(5) Uani 1 1 d . . . . .
C18 C 0.5523(2) 0.3222(2) 0.36206(13) 0.0251(6) Uani 1 1 d . . . . .
C19 C 0.5943(2) 0.4471(2) 0.38142(13) 0.0291(6) Uani 1 1 d . . . . .
H19 H 0.569820 0.501593 0.414726 0.035 Uiso 1 1 calc R U . . .
C20 C 0.6774(2) 0.4920(3) 0.34884(15) 0.0375(7) Uani 1 1 d . . . . .
H20 H 0.706923 0.580728 0.360624 0.045 Uiso 1 1 calc R U . . .
C21 C 0.7176(2) 0.4167(3) 0.30198(14) 0.0367(7) Uani 1 1 d . . . . .
H21 H 0.773262 0.452460 0.282248 0.044 Uiso 1 1 calc R U . . .
C22 C 0.67527(19) 0.2851(3) 0.28328(13) 0.0282(6) Uani 1 1 d . . . . .
C23 C 0.7060(2) 0.1847(3) 0.23693(13) 0.0340(7) Uani 1 1 d . . . . .
H23 H 0.762290 0.203693 0.213987 0.041 Uiso 1 1 calc R U . . .
C24 C 0.6533(2) 0.0622(3) 0.22652(13) 0.0317(6) Uani 1 1 d . . . . .
H24 H 0.674840 -0.002807 0.196065 0.038 Uiso 1 1 calc R U . . .
C25 C 0.5671(2) 0.0258(3) 0.25888(13) 0.0306(6) Uani 1 1 d . . . . .
H25 H 0.532405 -0.060725 0.250243 0.037 Uiso 1 1 calc R U . . .
C26 C 0.53732(19) 0.1193(3) 0.30210(12) 0.0239(6) Uani 1 1 d . . . . .
C27 C 0.59182(18) 0.2430(2) 0.31330(12) 0.0201(5) Uani 1 1 d . . . . .
C28 C 0.45210(19) 0.1235(2) 0.34396(12) 0.0232(5) Uani 1 1 d . . . . .
H28 H 0.388684 0.136429 0.315915 0.028 Uiso 1 1 calc R U . . .
C29 C 0.44059(18) -0.0027(2) 0.38571(12) 0.0201(5) Uani 1 1 d . . . . .
C30 C 0.52716(18) -0.0635(2) 0.42023(12) 0.0194(5) Uani 1 1 d . . . . .
C31 C 0.51816(18) -0.1986(2) 0.45693(12) 0.0214(5) Uani 1 1 d . . . . .
H31A H 0.518515 -0.176006 0.503016 0.026 Uiso 1 1 calc R U . . .
H31B H 0.576975 -0.258757 0.451329 0.026 Uiso 1 1 calc R U . . .
C32 C 0.42405(18) -0.2813(2) 0.43593(13) 0.0237(5) Uani 1 1 d . . . . .
H32A H 0.415982 -0.359798 0.466301 0.028 Uiso 1 1 calc R U . . .
H32B H 0.429898 -0.322724 0.393090 0.028 Uiso 1 1 calc R U . . .
C33 C 0.33306(18) -0.1849(2) 0.43351(12) 0.0224(5) Uani 1 1 d . . . . .
H33A H 0.273721 -0.237359 0.414892 0.027 Uiso 1 1 calc R U . . .
H33B H 0.320831 -0.156283 0.477517 0.027 Uiso 1 1 calc R U . . .
C34 C 0.34771(18) -0.0556(2) 0.39424(12) 0.0195(5) Uani 1 1 d . . . . .
H3A H -0.272(3) 0.905(3) 0.4360(18) 0.054(12) Uiso 1 1 d . . . . .
H6A H 0.212(3) -0.036(3) 0.3783(17) 0.057(10) 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
O1 C1 1.350(3) . ?
O1 C11 1.521(3) . ?
O2 C17 1.249(3) . ?
O3 C13 1.325(3) . ?
O3 H3A 0.75(4) . ?
O4 C18 1.364(3) . ?
O4 C28 1.508(3) . ?
O5 C30 1.248(3) . ?
O6 C34 1.322(3) . ?
O6 H6A 0.91(4) . ?
C1 C2 1.362(3) . ?
C1 C10 1.431(4) . ?
C2 C3 1.391(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.356(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(4) . ?
C4 H4 0.9500 . ?
C5 C10 1.391(4) . ?
C5 C6 1.429(4) . ?
C6 C7 1.408(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.417(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.344(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(4) . ?
C9 C11 1.493(4) . ?
C11 C12 1.500(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.367(3) . ?
C12 C17 1.439(3) . ?
C13 C14 1.497(3) . ?
C14 C15 1.524(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.522(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.502(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 C19 1.354(3) . ?
C18 C27 1.409(4) . ?
C19 C20 1.427(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.364(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.408(4) . ?
C21 H21 0.9500 . ?
C22 C27 1.394(3) . ?
C22 C23 1.445(4) . ?
C23 C24 1.364(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.438(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.352(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(3) . ?
C26 C28 1.506(4) . ?
C28 C29 1.496(3) . ?
C28 H28 1.0000 . ?
C29 C34 1.373(3) . ?
C29 C30 1.436(3) . ?
C30 C31 1.500(3) . ?
C31 C32 1.519(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.523(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.496(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C11 108.03(19) . . ?
C13 O3 H3A 113(3) . . ?
C18 O4 C28 107.81(18) . . ?
C34 O6 H6A 109(2) . . ?
O1 C1 C2 130.6(3) . . ?
O1 C1 C10 110.7(2) . . ?
C2 C1 C10 118.7(2) . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 123.9(3) . . ?
C4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C10 C5 C4 116.6(3) . . ?
C10 C5 C6 114.0(3) . . ?
C4 C5 C6 129.4(3) . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 117.1(3) . . ?
C8 C9 C11 134.7(3) . . ?
C10 C9 C11 108.2(2) . . ?
C9 C10 C5 127.9(3) . . ?
C9 C10 C1 109.5(2) . . ?
C5 C10 C1 122.6(2) . . ?
C9 C11 C12 119.4(2) . . ?
C9 C11 O1 103.55(19) . . ?
C12 C11 O1 107.82(19) . . ?
C9 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
O1 C11 H11 108.5 . . ?
C13 C12 C17 120.0(2) . . ?
C13 C12 C11 120.8(2) . . ?
C17 C12 C11 119.2(2) . . ?
O3 C13 C12 118.9(2) . . ?
O3 C13 C14 117.8(2) . . ?
C12 C13 C14 123.3(2) . . ?
C13 C14 C15 112.7(2) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 110.9(2) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 112.84(19) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
O2 C17 C12 120.1(2) . . ?
O2 C17 C16 120.3(2) . . ?
C12 C17 C16 119.6(2) . . ?
C19 C18 O4 128.7(3) . . ?
C19 C18 C27 120.4(2) . . ?
O4 C18 C27 110.9(2) . . ?
C18 C19 C20 116.0(3) . . ?
C18 C19 H19 122.0 . . ?
C20 C19 H19 122.0 . . ?
C21 C20 C19 124.7(3) . . ?
C21 C20 H20 117.7 . . ?
C19 C20 H20 117.7 . . ?
C20 C21 C22 119.0(3) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C27 C22 C21 116.6(3) . . ?
C27 C22 C23 114.1(2) . . ?
C21 C22 C23 129.3(3) . . ?
C24 C23 C22 119.2(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 123.9(3) . . ?
C23 C24 H24 118.1 . . ?
C25 C24 H24 118.1 . . ?
C26 C25 C24 117.4(2) . . ?
C26 C25 H25 121.3 . . ?
C24 C25 H25 121.3 . . ?
C25 C26 C27 118.7(2) . . ?
C25 C26 C28 134.0(2) . . ?
C27 C26 C28 107.3(2) . . ?
C26 C27 C22 126.8(2) . . ?
C26 C27 C18 110.0(2) . . ?
C22 C27 C18 123.2(2) . . ?
C29 C28 C26 116.4(2) . . ?
C29 C28 O4 111.4(2) . . ?
C26 C28 O4 103.75(18) . . ?
C29 C28 H28 108.3 . . ?
C26 C28 H28 108.3 . . ?
O4 C28 H28 108.3 . . ?
C34 C29 C30 119.8(2) . . ?
C34 C29 C28 120.6(2) . . ?
C30 C29 C28 119.5(2) . . ?
O5 C30 C29 120.4(2) . . ?
O5 C30 C31 119.6(2) . . ?
C29 C30 C31 120.0(2) . . ?
C30 C31 C32 113.0(2) . . ?
C30 C31 H31A 109.0 . . ?
C32 C31 H31A 109.0 . . ?
C30 C31 H31B 109.0 . . ?
C32 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 C33 110.46(19) . . ?
C31 C32 H32A 109.6 . . ?
C33 C32 H32A 109.6 . . ?
C31 C32 H32B 109.6 . . ?
C33 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
C34 C33 C32 111.2(2) . . ?
C34 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
C34 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
O6 C34 C29 119.3(2) . . ?
O6 C34 C33 118.4(2) . . ?
C29 C34 C33 122.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O1 C1 C2 179.2(2) . . . . ?
C11 O1 C1 C10 0.3(2) . . . . ?
O1 C1 C2 C3 179.5(2) . . . . ?
C10 C1 C2 C3 -1.6(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C10 -1.2(4) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
C10 C5 C6 C7 1.3(3) . . . . ?
C4 C5 C6 C7 -179.7(3) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 -1.1(4) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C7 C8 C9 C11 -176.4(3) . . . . ?
C8 C9 C10 C5 0.6(4) . . . . ?
C11 C9 C10 C5 178.5(2) . . . . ?
C8 C9 C10 C1 180.0(2) . . . . ?
C11 C9 C10 C1 -2.1(3) . . . . ?
C4 C5 C10 C9 179.3(2) . . . . ?
C6 C5 C10 C9 -1.6(4) . . . . ?
C4 C5 C10 C1 -0.1(3) . . . . ?
C6 C5 C10 C1 179.1(2) . . . . ?
O1 C1 C10 C9 1.1(3) . . . . ?
C2 C1 C10 C9 -177.9(2) . . . . ?
O1 C1 C10 C5 -179.4(2) . . . . ?
C2 C1 C10 C5 1.5(3) . . . . ?
C8 C9 C11 C12 -60.6(4) . . . . ?
C10 C9 C11 C12 122.0(2) . . . . ?
C8 C9 C11 O1 179.6(3) . . . . ?
C10 C9 C11 O1 2.2(2) . . . . ?
C1 O1 C11 C9 -1.5(2) . . . . ?
C1 O1 C11 C12 -128.9(2) . . . . ?
C9 C11 C12 C13 126.2(3) . . . . ?
O1 C11 C12 C13 -116.2(2) . . . . ?
C9 C11 C12 C17 -56.8(3) . . . . ?
O1 C11 C12 C17 60.8(3) . . . . ?
C17 C12 C13 O3 -176.5(2) . . . . ?
C11 C12 C13 O3 0.5(4) . . . . ?
C17 C12 C13 C14 0.9(4) . . . . ?
C11 C12 C13 C14 177.9(2) . . . . ?
O3 C13 C14 C15 -160.6(2) . . . . ?
C12 C13 C14 C15 22.0(4) . . . . ?
C13 C14 C15 C16 -46.7(3) . . . . ?
C14 C15 C16 C17 50.7(3) . . . . ?
C13 C12 C17 O2 -178.3(2) . . . . ?
C11 C12 C17 O2 4.6(3) . . . . ?
C13 C12 C17 C16 3.0(3) . . . . ?
C11 C12 C17 C16 -174.1(2) . . . . ?
C15 C16 C17 O2 151.8(2) . . . . ?
C15 C16 C17 C12 -29.5(3) . . . . ?
C28 O4 C18 C19 177.3(2) . . . . ?
C28 O4 C18 C27 -1.9(3) . . . . ?
O4 C18 C19 C20 -177.9(2) . . . . ?
C27 C18 C19 C20 1.2(4) . . . . ?
C18 C19 C20 C21 -1.9(4) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C20 C21 C22 C27 2.0(4) . . . . ?
C20 C21 C22 C23 -177.7(3) . . . . ?
C27 C22 C23 C24 0.1(3) . . . . ?
C21 C22 C23 C24 179.9(3) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C24 C25 C26 C27 -0.9(4) . . . . ?
C24 C25 C26 C28 178.3(3) . . . . ?
C25 C26 C27 C22 1.5(4) . . . . ?
C28 C26 C27 C22 -177.9(2) . . . . ?
C25 C26 C27 C18 -176.8(2) . . . . ?
C28 C26 C27 C18 3.8(3) . . . . ?
C21 C22 C27 C26 179.1(2) . . . . ?
C23 C22 C27 C26 -1.1(4) . . . . ?
C21 C22 C27 C18 -2.7(4) . . . . ?
C23 C22 C27 C18 177.0(2) . . . . ?
C19 C18 C27 C26 179.5(2) . . . . ?
O4 C18 C27 C26 -1.2(3) . . . . ?
C19 C18 C27 C22 1.1(4) . . . . ?
O4 C18 C27 C22 -179.6(2) . . . . ?
C25 C26 C28 C29 53.3(4) . . . . ?
C27 C26 C28 C29 -127.4(2) . . . . ?
C25 C26 C28 O4 176.1(3) . . . . ?
C27 C26 C28 O4 -4.7(2) . . . . ?
C18 O4 C28 C29 130.0(2) . . . . ?
C18 O4 C28 C26 4.0(2) . . . . ?
C26 C28 C29 C34 -139.9(2) . . . . ?
O4 C28 C29 C34 101.4(3) . . . . ?
C26 C28 C29 C30 43.9(3) . . . . ?
O4 C28 C29 C30 -74.7(3) . . . . ?
C34 C29 C30 O5 -167.2(2) . . . . ?
C28 C29 C30 O5 8.9(3) . . . . ?
C34 C29 C30 C31 10.0(3) . . . . ?
C28 C29 C30 C31 -173.8(2) . . . . ?
O5 C30 C31 C32 -163.9(2) . . . . ?
C29 C30 C31 C32 18.8(3) . . . . ?
C30 C31 C32 C33 -49.5(3) . . . . ?
C31 C32 C33 C34 52.4(3) . . . . ?
C30 C29 C34 O6 172.0(2) . . . . ?
C28 C29 C34 O6 -4.1(4) . . . . ?
C30 C29 C34 C33 -6.3(4) . . . . ?
C28 C29 C34 C33 177.6(2) . . . . ?
C32 C33 C34 O6 156.1(2) . . . . ?
C32 C33 C34 C29 -25.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O5 0.75(4) 1.83(4) 2.569(3) 173(4) 1_465
O6 H6A O2 0.91(4) 1.64(4) 2.547(2) 174(3) 1_545

_refine_diff_density_max         1.007
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.065

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
