# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cxy0053
_database_code_depnum_ccdc_archive 'CCDC 1557114'
_audit_update_record             
;
2017-06-20 deposited with the CCDC.
2017-07-26 downloaded from the CCDC.
;
_audit_creation_date             2017-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   9.8300(5)
_cell_length_b                   10.1369(4)
_cell_length_c                   12.4497(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.021(2)
_cell_angle_gamma                90
_cell_volume                     1235.80(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8985
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0797 before and 0.0517 after correction. The Ratio of minimum to maximum transmission is 0.9439. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16855
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_min         2.892
_diffrn_ambient_temperature      150.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2379
_reflns_number_total             2828
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2828
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.4710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.00792(10) 0.35001(10) 0.40609(7) 0.0274(2) Uani 1 1 d . . . . .
H1 H 1.090102 0.326388 0.409703 0.041 Uiso 1 1 calc GR . . . .
O2 O 0.72751(10) 0.70978(10) 0.54968(8) 0.0278(2) Uani 1 1 d . . . . .
N1 N 0.51025(11) 0.69086(11) 0.46798(9) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.44328(15) 0.77734(14) 0.54025(11) 0.0285(3) Uani 1 1 d . . . . .
H1A H 0.504913 0.794247 0.604976 0.043 Uiso 1 1 calc GR . . . .
H1B H 0.359738 0.735075 0.560833 0.043 Uiso 1 1 calc GR . . . .
H1C H 0.420042 0.860972 0.503635 0.043 Uiso 1 1 calc GR . . . .
C2 C 0.44453(13) 0.62588(12) 0.37822(10) 0.0202(3) Uani 1 1 d . . . . .
C3 C 0.30778(14) 0.63074(14) 0.34112(11) 0.0250(3) Uani 1 1 d . . . . .
H3 H 0.245245 0.684669 0.375211 0.030 Uiso 1 1 calc R . . . .
C4 C 0.26536(14) 0.55370(13) 0.25203(12) 0.0267(3) Uani 1 1 d . . . . .
H4 H 0.172691 0.557128 0.223213 0.032 Uiso 1 1 calc R . . . .
C5 C 0.35619(14) 0.47175(14) 0.20442(11) 0.0257(3) Uani 1 1 d . . . . .
H5 H 0.323903 0.416749 0.145860 0.031 Uiso 1 1 calc R . . . .
C6 C 0.49429(14) 0.46931(13) 0.24163(10) 0.0218(3) Uani 1 1 d . . . . .
H6 H 0.555963 0.413289 0.208620 0.026 Uiso 1 1 calc R . . . .
C7 C 0.54056(13) 0.54993(12) 0.32764(10) 0.0188(3) Uani 1 1 d . . . . .
C8 C 0.67354(13) 0.57164(12) 0.38815(10) 0.0193(3) Uani 1 1 d . . . . .
C9 C 0.64610(13) 0.66227(13) 0.47905(10) 0.0210(3) Uani 1 1 d . . . . .
C10 C 0.80163(13) 0.53036(12) 0.37591(10) 0.0201(3) Uani 1 1 d . . . . .
H10 H 0.867135 0.547115 0.435041 0.024 Uiso 1 1 calc R . . . .
C11 C 0.85321(13) 0.46318(12) 0.28368(10) 0.0181(3) Uani 1 1 d . . . . .
C12 C 0.80971(13) 0.49657(13) 0.17695(10) 0.0216(3) Uani 1 1 d . . . . .
H12 H 0.736399 0.556983 0.163027 0.026 Uiso 1 1 calc R . . . .
C13 C 0.87184(14) 0.44296(14) 0.09160(10) 0.0257(3) Uani 1 1 d . . . . .
H13 H 0.842032 0.467289 0.019677 0.031 Uiso 1 1 calc R . . . .
C14 C 0.97788(14) 0.35352(14) 0.11136(11) 0.0266(3) Uani 1 1 d . . . . .
H14 H 1.019276 0.315310 0.052621 0.032 Uiso 1 1 calc R . . . .
C15 C 1.02385(13) 0.31948(13) 0.21585(11) 0.0231(3) Uani 1 1 d . . . . .
H15 H 1.096179 0.257789 0.228800 0.028 Uiso 1 1 calc R . . . .
C16 C 0.96368(13) 0.37604(12) 0.30207(10) 0.0187(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C16 1.3555(15) . ?
O2 C9 1.2339(16) . ?
N1 C1 1.4544(16) . ?
N1 C2 1.4048(17) . ?
N1 C9 1.3616(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.3835(19) . ?
C2 C7 1.4088(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3958(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3915(18) . ?
C7 C8 1.4670(18) . ?
C8 C9 1.5002(17) . ?
C8 C10 1.3481(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.4633(17) . ?
C11 C12 1.4013(18) . ?
C11 C16 1.4030(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3824(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.3935(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 H1 109.5 . . ?
C2 N1 C1 124.97(11) . . ?
C9 N1 C1 123.97(11) . . ?
C9 N1 C2 111.06(10) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C7 109.41(11) . . ?
C3 C2 N1 127.93(12) . . ?
C3 C2 C7 122.67(12) . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.46(13) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.13(13) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.77(13) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.21(12) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C8 106.88(11) . . ?
C6 C7 C2 118.57(12) . . ?
C6 C7 C8 134.42(12) . . ?
C7 C8 C9 105.56(10) . . ?
C10 C8 C7 133.98(12) . . ?
C10 C8 C9 120.44(12) . . ?
O2 C9 N1 123.93(12) . . ?
O2 C9 C8 128.94(12) . . ?
N1 C9 C8 107.07(11) . . ?
C8 C10 H10 115.7 . . ?
C8 C10 C11 128.64(12) . . ?
C11 C10 H10 115.7 . . ?
C12 C11 C10 122.26(12) . . ?
C12 C11 C16 118.32(11) . . ?
C16 C11 C10 118.78(11) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.01(13) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.75(12) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.57(12) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.74(12) . . ?
C16 C15 H15 120.1 . . ?
O1 C16 C11 117.23(11) . . ?
O1 C16 C15 122.24(11) . . ?
C15 C16 C11 120.53(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_cxy0044_0m
_database_code_depnum_ccdc_archive 'CCDC 1555430'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2017-07-26 downloaded from the CCDC.
;
_audit_creation_date             2017-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 O3'
_chemical_formula_sum            'C15 H10 O3'
_chemical_formula_weight         238.23
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.8423(6)
_cell_length_b                   10.7141(10)
_cell_length_c                   17.7750(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1112.63(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8736
_cell_measurement_temperature    150.35
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1689 before and 0.0981 after correction. The Ratio of minimum to maximum transmission is 0.7052. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15086
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_min         2.292
_diffrn_ambient_temperature      150.35
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2319
_reflns_number_total             2567
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 887 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.2289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1029
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8953(3) 0.49762(15) 0.28041(8) 0.0228(4) Uani 1 1 d . . . . .
O2 O 0.8101(3) 0.47541(14) 0.40025(8) 0.0176(4) Uani 1 1 d . . . . .
O3 O 0.8810(3) 0.21660(15) 0.24739(9) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.950207 0.154530 0.229628 0.037 Uiso 1 1 calc GR . . . .
C1 C 0.6582(4) 0.44354(19) 0.45626(11) 0.0148(4) Uani 1 1 d . . . . .
C2 C 0.7230(4) 0.4704(2) 0.52982(11) 0.0189(5) Uani 1 1 d . . . . .
H2 H 0.865834 0.508948 0.540308 0.023 Uiso 1 1 calc R . . . .
C3 C 0.5739(4) 0.4394(2) 0.58721(11) 0.0211(5) Uani 1 1 d . . . . .
H3A H 0.615505 0.456232 0.637867 0.025 Uiso 1 1 calc R . . . .
C4 C 0.3626(4) 0.3836(2) 0.57176(11) 0.0213(5) Uani 1 1 d . . . . .
H4 H 0.261695 0.362929 0.611778 0.026 Uiso 1 1 calc R . . . .
C5 C 0.3007(4) 0.35842(19) 0.49819(12) 0.0172(5) Uani 1 1 d . . . . .
H5 H 0.156136 0.321682 0.487803 0.021 Uiso 1 1 calc R . . . .
C6 C 0.4503(4) 0.38685(19) 0.43877(11) 0.0139(4) Uani 1 1 d . . . . .
C7 C 0.4090(4) 0.35253(19) 0.36169(12) 0.0143(4) Uani 1 1 d . . . . .
H7 H 0.269768 0.312013 0.348786 0.017 Uiso 1 1 calc R . . . .
C8 C 0.5641(4) 0.37677(19) 0.30736(11) 0.0145(4) Uani 1 1 d . . . . .
C9 C 0.5417(4) 0.33137(19) 0.22885(11) 0.0153(4) Uani 1 1 d . . . . .
C10 C 0.3539(4) 0.3620(2) 0.18462(12) 0.0189(5) Uani 1 1 d . . . . .
H10 H 0.239345 0.416280 0.203810 0.023 Uiso 1 1 calc R . . . .
C11 C 0.3326(4) 0.3133(2) 0.11208(12) 0.0225(5) Uani 1 1 d . . . . .
H11 H 0.203565 0.334159 0.082069 0.027 Uiso 1 1 calc R . . . .
C12 C 0.4992(5) 0.2347(2) 0.08408(12) 0.0227(5) Uani 1 1 d . . . . .
H12 H 0.484970 0.202652 0.034481 0.027 Uiso 1 1 calc R . . . .
C13 C 0.6870(4) 0.2021(2) 0.12741(12) 0.0212(5) Uani 1 1 d . . . . .
H13 H 0.801326 0.148315 0.107581 0.025 Uiso 1 1 calc R . . . .
C14 C 0.7071(4) 0.2491(2) 0.20068(11) 0.0169(5) Uani 1 1 d . . . . .
C15 C 0.7648(4) 0.4520(2) 0.32553(11) 0.0159(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 C15 1.210(3) . ?
O2 C1 1.377(3) . ?
O2 C15 1.377(2) . ?
O3 H3 0.8400 . ?
O3 C14 1.357(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.399(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(3) . ?
C6 C7 1.439(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.350(3) . ?
C8 C9 1.484(3) . ?
C8 C15 1.459(3) . ?
C9 C10 1.389(3) . ?
C9 C14 1.401(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.397(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.401(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
C1 O2 C15 121.90(17) . . ?
C14 O3 H3 109.5 . . ?
O2 C1 C2 116.9(2) . . ?
O2 C1 C6 120.57(17) . . ?
C2 C1 C6 122.5(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3A 119.5 . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 117.98(18) . . ?
C1 C6 C7 118.04(19) . . ?
C5 C6 C7 123.8(2) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 123.4(2) . . ?
C7 C8 C15 119.18(19) . . ?
C15 C8 C9 117.40(18) . . ?
C10 C9 C8 121.63(19) . . ?
C10 C9 C14 119.43(19) . . ?
C14 C9 C8 118.80(19) . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
O3 C14 C9 117.32(18) . . ?
O3 C14 C13 122.6(2) . . ?
C9 C14 C13 120.0(2) . . ?
O1 C15 O2 116.40(19) . . ?
O1 C15 C8 125.66(19) . . ?
O2 C15 C8 117.94(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_cxy0011_0m
_database_code_depnum_ccdc_archive 'CCDC 1555429'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2017-07-26 downloaded from the CCDC.
;
_audit_creation_date             2017-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   11.3554(5)
_cell_length_b                   9.9923(4)
_cell_length_c                   15.6896(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.418(2)
_cell_angle_gamma                90
_cell_volume                     1716.18(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1245 before and 0.0560 after correction. The Ratio of minimum to maximum transmission is 0.9529. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27162
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.443
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3403
_reflns_number_total             4258
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+0.6452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1134
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50208(8) 0.74672(9) 0.41285(6) 0.0250(2) Uani 1 1 d . . . . .
O2 O 0.35629(8) 0.83049(9) 0.30481(6) 0.0288(2) Uani 1 1 d . . . . .
O3 O -0.00947(10) 0.52267(13) 0.18184(7) 0.0475(3) Uani 1 1 d . . . . .
O4 O 0.01822(8) 0.66534(9) 0.29896(6) 0.0275(2) Uani 1 1 d . . . . .
N1 N 0.16094(9) 0.65228(11) 0.22847(7) 0.0242(2) Uani 1 1 d . . . . .
H1 H 0.1986 0.7077 0.2705 0.029 Uiso 1 1 calc R . . . .
C1 C 0.57852(11) 0.64415(12) 0.45150(8) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.65369(12) 0.66676(14) 0.53576(9) 0.0298(3) Uani 1 1 d . . . . .
H2 H 0.6526 0.7502 0.5646 0.036 Uiso 1 1 calc R . . . .
C3 C 0.73022(12) 0.56448(15) 0.57666(9) 0.0326(3) Uani 1 1 d . . . . .
H3 H 0.7826 0.5781 0.6342 0.039 Uiso 1 1 calc R . . . .
C4 C 0.73163(12) 0.44195(14) 0.53470(9) 0.0301(3) Uani 1 1 d . . . . .
H4 H 0.7839 0.3723 0.5640 0.036 Uiso 1 1 calc R . . . .
C5 C 0.65739(11) 0.42153(13) 0.45077(9) 0.0268(3) Uani 1 1 d . . . . .
H5 H 0.6590 0.3380 0.4221 0.032 Uiso 1 1 calc R . . . .
C6 C 0.57924(11) 0.52381(12) 0.40733(8) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.50030(11) 0.51148(13) 0.31968(8) 0.0234(3) Uani 1 1 d . . . . .
H7 H 0.5013 0.4308 0.2878 0.028 Uiso 1 1 calc R . . . .
C8 C 0.42439(10) 0.61138(12) 0.28098(8) 0.0214(2) Uani 1 1 d . . . . .
C9 C 0.42209(10) 0.73495(12) 0.33056(8) 0.0217(2) Uani 1 1 d . . . . .
C10 C 0.34850(11) 0.60050(12) 0.18805(8) 0.0227(3) Uani 1 1 d . . . . .
C11 C 0.40625(12) 0.56627(14) 0.12262(9) 0.0286(3) Uani 1 1 d . . . . .
H11 H 0.4922 0.5533 0.1385 0.034 Uiso 1 1 calc R . . . .
C12 C 0.34062(14) 0.55092(14) 0.03516(9) 0.0334(3) Uani 1 1 d . . . . .
H12 H 0.3815 0.5281 -0.0084 0.040 Uiso 1 1 calc R . . . .
C13 C 0.21518(14) 0.56897(15) 0.01145(9) 0.0331(3) Uani 1 1 d . . . . .
H13 H 0.1698 0.5584 -0.0485 0.040 Uiso 1 1 calc R . . . .
C14 C 0.15585(12) 0.60244(14) 0.07508(8) 0.0286(3) Uani 1 1 d . . . . .
H14 H 0.0698 0.6147 0.0584 0.034 Uiso 1 1 calc R . . . .
C15 C 0.22105(11) 0.61826(12) 0.16314(8) 0.0232(3) Uani 1 1 d . . . . .
C16 C 0.04921(12) 0.60568(13) 0.23113(8) 0.0265(3) Uani 1 1 d . . . . .
C17 C -0.09225(11) 0.62254(14) 0.32462(9) 0.0292(3) Uani 1 1 d . . . . .
C18 C -0.08753(15) 0.70936(17) 0.40468(11) 0.0440(4) Uani 1 1 d . . . . .
H18A H -0.0116 0.6915 0.4504 0.066 Uiso 1 1 calc GR . . . .
H18B H -0.1576 0.6888 0.4278 0.066 Uiso 1 1 calc GR . . . .
H18C H -0.0903 0.8039 0.3876 0.066 Uiso 1 1 calc GR . . . .
C19 C -0.20563(14) 0.6512(2) 0.25064(12) 0.0548(5) Uani 1 1 d . . . . .
H19A H -0.2077 0.7463 0.2351 0.082 Uiso 1 1 calc GR . . . .
H19B H -0.2784 0.6287 0.2701 0.082 Uiso 1 1 calc GR . . . .
H19C H -0.2042 0.5972 0.1988 0.082 Uiso 1 1 calc GR . . . .
C20 C -0.08100(15) 0.47586(16) 0.34998(12) 0.0443(4) Uani 1 1 d . . . . .
H20A H -0.0796 0.4219 0.2981 0.066 Uiso 1 1 calc GR . . . .
H20B H -0.1509 0.4493 0.3717 0.066 Uiso 1 1 calc GR . . . .
H20C H -0.0052 0.4615 0.3965 0.066 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3755(15) . ?
O1 C9 1.3719(14) . ?
O2 C9 1.2134(15) . ?
O3 C16 1.2067(16) . ?
O4 C16 1.3457(16) . ?
O4 C17 1.4789(15) . ?
N1 H1 0.8800 . ?
N1 C15 1.4158(16) . ?
N1 C16 1.3624(16) . ?
C1 C2 1.3884(18) . ?
C1 C6 1.3890(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3770(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.4053(17) . ?
C6 C7 1.4333(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3527(17) . ?
C8 C9 1.4632(17) . ?
C8 C10 1.4874(16) . ?
C10 C11 1.3996(17) . ?
C10 C15 1.4064(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3850(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.3857(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3921(17) . ?
C17 C18 1.516(2) . ?
C17 C19 1.514(2) . ?
C17 C20 1.515(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 122.23(10) . . ?
C16 O4 C17 120.41(10) . . ?
C15 N1 H1 117.5 . . ?
C16 N1 H1 117.5 . . ?
C16 N1 C15 124.91(11) . . ?
O1 C1 C2 117.05(11) . . ?
O1 C1 C6 120.79(11) . . ?
C2 C1 C6 122.16(12) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.21(13) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.00(12) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.10(12) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.21(12) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.32(11) . . ?
C1 C6 C7 117.90(11) . . ?
C5 C6 C7 123.78(11) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 121.91(11) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 C9 118.91(11) . . ?
C7 C8 C10 121.33(11) . . ?
C9 C8 C10 119.68(10) . . ?
O1 C9 C8 118.14(10) . . ?
O2 C9 O1 116.16(11) . . ?
O2 C9 C8 125.69(11) . . ?
C11 C10 C8 118.33(11) . . ?
C11 C10 C15 118.37(11) . . ?
C15 C10 C8 123.27(11) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.34(12) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.73(13) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.01(12) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.68(12) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 N1 119.19(11) . . ?
C14 C15 N1 120.94(11) . . ?
C14 C15 C10 119.87(12) . . ?
O3 C16 O4 126.54(12) . . ?
O3 C16 N1 125.12(13) . . ?
O4 C16 N1 108.32(11) . . ?
O4 C17 C18 102.38(11) . . ?
O4 C17 C19 110.28(11) . . ?
O4 C17 C20 109.44(11) . . ?
C19 C17 C18 111.26(14) . . ?
C19 C17 C20 112.30(14) . . ?
C20 C17 C18 110.74(13) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
