# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_VP7_019_Sarpong
_database_code_depnum_ccdc_archive 'CCDC 2034052'
loop_
_audit_author_name
_audit_author_address
'Nicholas Settineri'
;University of California, Berkeley
United States of America
;
_audit_update_record             
;
2020-09-26 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 N O2'
_chemical_formula_sum            'C14 H11 N O2'
_chemical_formula_weight         225.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.04510(10)
_cell_length_b                   13.6147(3)
_cell_length_c                   15.6358(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.956(2)
_cell_angle_gamma                90
_cell_volume                     1071.43(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10232
_cell_measurement_theta_min      3.2300
_cell_measurement_theta_max      78.6280

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.764
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            12038
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.1153
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.310
_diffrn_reflns_theta_max         74.502
_diffrn_reflns_theta_full        74.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2171
_reflns_number_gt                2065
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_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)+(0.1112P)²+0.3772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2171
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1667
_refine_ls_wR_factor_gt          0.1650
_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
C1 C 0.2687(3) 0.74385(10) 0.40248(9) 0.0179(4) Uani 1 1 d . . . . .
C2 C 0.3926(3) 0.67505(10) 0.45525(9) 0.0185(4) Uani 1 1 d . . . . .
H2 H 0.3626 0.6640 0.5138 0.022 Uiso 1 1 calc R U . . .
C3 C 0.5744(3) 0.62318(10) 0.40630(9) 0.0180(4) Uani 1 1 d . . . . .
C4 C 0.7509(3) 0.54475(11) 0.42518(9) 0.0199(4) Uani 1 1 d . . . . .
H4 H 0.7621 0.5152 0.4804 0.024 Uiso 1 1 calc R U . . .
C5 C 0.9073(3) 0.51146(11) 0.36216(9) 0.0212(4) Uani 1 1 d . . . . .
H5 H 1.0259 0.4583 0.3744 0.025 Uiso 1 1 calc R U . . .
C6 C 0.8947(3) 0.55458(11) 0.28006(9) 0.0210(4) Uani 1 1 d . . . . .
H6 H 1.0076 0.5309 0.2385 0.025 Uiso 1 1 calc R U . . .
C7 C 0.7206(3) 0.63079(11) 0.25893(9) 0.0201(4) Uani 1 1 d . . . . .
H7 H 0.7102 0.6597 0.2035 0.024 Uiso 1 1 calc R U . . .
C8 C 0.5608(3) 0.66332(10) 0.32283(9) 0.0175(4) Uani 1 1 d . . . . .
C9 C 0.2865(3) 0.79596(11) 0.25270(9) 0.0207(4) Uani 1 1 d . . . . .
H9 H 0.3612 0.7888 0.1989 0.025 Uiso 1 1 calc R U . . .
C10 C 0.0952(3) 0.86421(11) 0.26268(9) 0.0225(4) Uani 1 1 d . . . . .
H10 H 0.0366 0.9052 0.2160 0.027 Uiso 1 1 calc R U . . .
C11 C -0.0174(3) 0.87423(11) 0.34311(9) 0.0213(4) Uani 1 1 d . . . . .
H11 H -0.1520 0.9220 0.3495 0.026 Uiso 1 1 calc R U . . .
C12 C 0.0644(3) 0.81634(10) 0.41161(9) 0.0182(4) Uani 1 1 d . . . . .
C13 C -0.0524(3) 0.82472(11) 0.49553(9) 0.0196(4) Uani 1 1 d . . . . .
C14 C -0.3658(3) 0.90371(13) 0.57581(10) 0.0277(4) Uani 1 1 d . . . . .
H14A H -0.4988 0.9562 0.5710 0.042 Uiso 1 1 calc R U . . .
H14B H -0.2314 0.9194 0.6221 0.042 Uiso 1 1 calc R U . . .
H14C H -0.4525 0.8415 0.5886 0.042 Uiso 1 1 calc R U . . .
N1 N 0.3717(2) 0.73749(9) 0.32034(7) 0.0174(3) Uani 1 1 d . . . . .
O1 O 0.0118(2) 0.77532(8) 0.55807(7) 0.0247(3) Uani 1 1 d . . . . .
O2 O -0.2402(2) 0.89489(8) 0.49606(7) 0.0250(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.370(2) . ?
C1 N1 1.4212(17) . ?
C1 C12 1.441(2) . ?
C2 C3 1.422(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.408(2) . ?
C3 C8 1.4122(19) . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.409(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3983(19) . ?
C7 H7 0.9500 . ?
C8 N1 1.3879(18) . ?
C9 C10 1.356(2) . ?
C9 N1 1.3690(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.422(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.370(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.4794(19) . ?
C13 O1 1.2123(18) . ?
C13 O2 1.3461(17) . ?
C14 O2 1.4421(17) . ?
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
C2 C1 N1 108.80(12) . . ?
C2 C1 C12 135.09(14) . . ?
N1 C1 C12 116.10(12) . . ?
C1 C2 C3 107.45(12) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
C4 C3 C8 118.49(13) . . ?
C4 C3 C2 133.27(13) . . ?
C8 C3 C2 108.24(12) . . ?
C5 C4 C3 118.90(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.42(14) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.18(13) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 117.02(13) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 H7 121.5 . . ?
N1 C8 C7 129.74(13) . . ?
N1 C8 C3 107.28(12) . . ?
C7 C8 C3 122.96(14) . . ?
C10 C9 N1 119.83(13) . . ?
C10 C9 H9 120.1 . . ?
N1 C9 H9 120.1 . . ?
C9 C10 C11 119.90(13) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 121.25(13) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C1 119.70(13) . . ?
C11 C12 C13 122.13(13) . . ?
C1 C12 C13 118.17(13) . . ?
O1 C13 O2 122.54(13) . . ?
O1 C13 C12 124.88(13) . . ?
O2 C13 C12 112.58(12) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 N1 C8 128.56(12) . . ?
C9 N1 C1 123.22(12) . . ?
C8 N1 C1 108.21(11) . . ?
C13 O2 C14 114.58(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.74(16) . . . . ?
C12 C1 C2 C3 178.18(16) . . . . ?
C1 C2 C3 C4 -178.83(15) . . . . ?
C1 C2 C3 C8 0.94(16) . . . . ?
C8 C3 C4 C5 1.3(2) . . . . ?
C2 C3 C4 C5 -178.96(14) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C7 -1.4(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 N1 179.72(13) . . . . ?
C6 C7 C8 C3 1.1(2) . . . . ?
C4 C3 C8 N1 179.04(12) . . . . ?
C2 C3 C8 N1 -0.77(16) . . . . ?
C4 C3 C8 C7 -2.1(2) . . . . ?
C2 C3 C8 C7 178.10(13) . . . . ?
N1 C9 C10 C11 -0.5(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C1 0.1(2) . . . . ?
C10 C11 C12 C13 -179.24(13) . . . . ?
C2 C1 C12 C11 -179.19(15) . . . . ?
N1 C1 C12 C11 -0.3(2) . . . . ?
C2 C1 C12 C13 0.2(3) . . . . ?
N1 C1 C12 C13 179.03(11) . . . . ?
C11 C12 C13 O1 179.79(14) . . . . ?
C1 C12 C13 O1 0.5(2) . . . . ?
C11 C12 C13 O2 -0.8(2) . . . . ?
C1 C12 C13 O2 179.92(12) . . . . ?
C10 C9 N1 C8 179.08(14) . . . . ?
C10 C9 N1 C1 0.2(2) . . . . ?
C7 C8 N1 C9 2.6(2) . . . . ?
C3 C8 N1 C9 -178.68(13) . . . . ?
C7 C8 N1 C1 -178.45(14) . . . . ?
C3 C8 N1 C1 0.31(15) . . . . ?
C2 C1 N1 C9 179.33(13) . . . . ?
C12 C1 N1 C9 0.2(2) . . . . ?
C2 C1 N1 C8 0.27(16) . . . . ?
C12 C1 N1 C8 -178.88(12) . . . . ?
O1 C13 O2 C14 -2.4(2) . . . . ?
C12 C13 O2 C14 178.16(12) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_VP8_029
_database_code_depnum_ccdc_archive 'CCDC 2034053'
loop_
_audit_author_name
_audit_author_address
'Nicholas Settineri'
;University of California, Berkeley
United States of America
;
_audit_update_record             
;
2020-09-26 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Cl N O2'
_chemical_formula_sum            'C14 H10 Cl N O2'
_chemical_formula_weight         259.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.64150(10)
_cell_length_b                   14.2584(3)
_cell_length_c                   9.2288(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.831(2)
_cell_angle_gamma                90
_cell_volume                     1126.51(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7966
_cell_measurement_theta_min      3.1000
_cell_measurement_theta_max      77.4220

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.942
_shelx_estimated_absorpt_T_min   0.202
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            12636
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.749
_diffrn_reflns_theta_max         74.442
_diffrn_reflns_theta_full        74.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2301
_reflns_number_gt                2087
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0560P)²+0.4543P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2301
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32259(17) 0.60162(11) 0.45086(16) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.44249(17) 0.59598(11) 0.35911(16) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.44412(19) 0.56891(11) 0.21271(16) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.3508 0.5508 0.1527 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5859(2) 0.56958(11) 0.15904(17) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.5894 0.5517 0.0604 0.025 Uiso 1 1 calc R U . . .
C5 C 0.72534(18) 0.59615(12) 0.24691(17) 0.0211(3) Uani 1 1 d . . . . .
H5 H 0.8206 0.5952 0.2063 0.025 Uiso 1 1 calc R U . . .
C6 C 0.72660(18) 0.62346(11) 0.39042(16) 0.0189(3) Uani 1 1 d . . . . .
H6 H 0.8204 0.6412 0.4501 0.023 Uiso 1 1 calc R U . . .
C7 C 0.58304(18) 0.62366(10) 0.44343(16) 0.0169(3) Uani 1 1 d . . . . .
C8 C 0.65344(18) 0.67810(11) 0.69811(16) 0.0191(3) Uani 1 1 d . . . . .
H8 H 0.7601 0.6875 0.6872 0.023 Uiso 1 1 calc R U . . .
C9 C 0.60307(18) 0.69519(11) 0.82737(16) 0.0201(3) Uani 1 1 d . . . . .
H9 H 0.6742 0.7161 0.9085 0.024 Uiso 1 1 calc R U . . .
C10 C 0.44317(18) 0.68184(11) 0.84172(16) 0.0193(3) Uani 1 1 d . . . . .
H10 H 0.4091 0.6929 0.9338 0.023 Uiso 1 1 calc R U . . .
C11 C 0.33653(17) 0.65343(11) 0.72641(16) 0.0177(3) Uani 1 1 d . . . . .
C12 C 0.16874(18) 0.65090(11) 0.74777(16) 0.0189(3) Uani 1 1 d . . . . .
C13 C 0.00023(19) 0.62847(13) 0.92552(18) 0.0257(4) Uani 1 1 d . . . . .
H13A H -0.0667 0.5825 0.8683 0.038 Uiso 1 1 calc R U . . .
H13B H -0.0423 0.6916 0.9055 0.038 Uiso 1 1 calc R U . . .
H13C H 0.0041 0.6146 1.0299 0.038 Uiso 1 1 calc R U . . .
C14 C 0.38765(17) 0.63382(11) 0.58762(16) 0.0166(3) Uani 1 1 d . . . . .
Cl1 Cl 0.13569(4) 0.56299(3) 0.39528(4) 0.02025(14) Uani 1 1 d . . . . .
N1 N 0.54938(14) 0.64697(9) 0.58191(13) 0.0166(3) Uani 1 1 d . . . . .
O1 O 0.05924(12) 0.67279(8) 0.65892(11) 0.0225(3) Uani 1 1 d . . . . .
O2 O 0.15524(13) 0.62376(9) 0.88578(11) 0.0231(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C14 1.388(2) . ?
C1 C2 1.427(2) . ?
C1 Cl1 1.7173(15) . ?
C2 C7 1.407(2) . ?
C2 C3 1.407(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C7 N1 1.3891(19) . ?
C8 C9 1.347(2) . ?
C8 N1 1.3758(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.419(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(2) . ?
C10 H10 0.9500 . ?
C11 C14 1.438(2) . ?
C11 C12 1.490(2) . ?
C12 O1 1.2057(18) . ?
C12 O2 1.3514(18) . ?
C13 O2 1.4378(18) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N1 1.4181(19) . ?

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 C1 C2 108.74(13) . . ?
C14 C1 Cl1 128.73(12) . . ?
C2 C1 Cl1 122.28(11) . . ?
C7 C2 C3 119.16(14) . . ?
C7 C2 C1 107.33(13) . . ?
C3 C2 C1 133.50(14) . . ?
C4 C3 C2 117.87(14) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.71(14) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.51(14) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 116.53(14) . . ?
C5 C6 H6 121.7 . . ?
C7 C6 H6 121.7 . . ?
N1 C7 C6 129.14(14) . . ?
N1 C7 C2 107.62(13) . . ?
C6 C7 C2 123.22(14) . . ?
C9 C8 N1 119.54(14) . . ?
C9 C8 H8 120.2 . . ?
N1 C8 H8 120.2 . . ?
C8 C9 C10 119.66(14) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 121.84(14) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C14 119.56(14) . . ?
C10 C11 C12 117.90(13) . . ?
C14 C11 C12 122.39(13) . . ?
O1 C12 O2 123.68(14) . . ?
O1 C12 C11 126.26(14) . . ?
O2 C12 C11 110.00(13) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 N1 106.80(13) . . ?
C1 C14 C11 137.62(14) . . ?
N1 C14 C11 115.55(13) . . ?
C8 N1 C7 126.70(13) . . ?
C8 N1 C14 123.81(13) . . ?
C7 N1 C14 109.49(12) . . ?
C12 O2 C13 115.47(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C7 1.13(18) . . . . ?
Cl1 C1 C2 C7 -173.62(11) . . . . ?
C14 C1 C2 C3 -179.66(17) . . . . ?
Cl1 C1 C2 C3 5.6(3) . . . . ?
C7 C2 C3 C4 0.9(2) . . . . ?
C1 C2 C3 C4 -178.20(16) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 N1 179.54(15) . . . . ?
C5 C6 C7 C2 1.4(2) . . . . ?
C3 C2 C7 N1 179.74(14) . . . . ?
C1 C2 C7 N1 -0.92(17) . . . . ?
C3 C2 C7 C6 -1.7(2) . . . . ?
C1 C2 C7 C6 177.60(15) . . . . ?
N1 C8 C9 C10 -0.7(2) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
C9 C10 C11 C14 1.8(2) . . . . ?
C9 C10 C11 C12 -173.77(15) . . . . ?
C10 C11 C12 O1 141.42(17) . . . . ?
C14 C11 C12 O1 -34.0(2) . . . . ?
C10 C11 C12 O2 -36.0(2) . . . . ?
C14 C11 C12 O2 148.56(15) . . . . ?
C2 C1 C14 N1 -0.88(17) . . . . ?
Cl1 C1 C14 N1 173.43(12) . . . . ?
C2 C1 C14 C11 -178.70(17) . . . . ?
Cl1 C1 C14 C11 -4.4(3) . . . . ?
C10 C11 C14 C1 177.08(18) . . . . ?
C12 C11 C14 C1 -7.5(3) . . . . ?
C10 C11 C14 N1 -0.6(2) . . . . ?
C12 C11 C14 N1 174.79(14) . . . . ?
C9 C8 N1 C7 -178.02(15) . . . . ?
C9 C8 N1 C14 1.9(2) . . . . ?
C6 C7 N1 C8 1.9(3) . . . . ?
C2 C7 N1 C8 -179.66(14) . . . . ?
C6 C7 N1 C14 -178.02(15) . . . . ?
C2 C7 N1 C14 0.39(17) . . . . ?
C1 C14 N1 C8 -179.64(14) . . . . ?
C11 C14 N1 C8 -1.3(2) . . . . ?
C1 C14 N1 C7 0.31(17) . . . . ?
C11 C14 N1 C7 178.68(13) . . . . ?
O1 C12 O2 C13 -4.1(2) . . . . ?
C11 C12 O2 C13 173.37(13) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_MPerea002_Sarpong
_database_code_depnum_ccdc_archive 'CCDC 2034054'
loop_
_audit_author_name
_audit_author_address
'Nicholas Settineri'
;University of California, Berkeley
United States of America
;
_audit_update_record             
;
2020-09-26 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 N O2'
_chemical_formula_sum            'C21 H15 N O2'
_chemical_formula_weight         313.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   10.1840(3)
_cell_length_b                   11.0563(3)
_cell_length_c                   14.3733(3)
_cell_angle_alpha                69.266(2)
_cell_angle_beta                 87.583(2)
_cell_angle_gamma                89.765(2)
_cell_volume                     1512.13(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    41267
_cell_measurement_theta_min      3.2730
_cell_measurement_theta_max      78.7180

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88354
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            59212
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.291
_diffrn_reflns_theta_max         74.475
_diffrn_reflns_theta_full        74.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6158
_reflns_number_gt                5765
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0459P)²+0.5633P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6158
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.46717(12) 0.62700(12) 0.30486(9) 0.0263(2) Uani 1 1 d . . . . .
H1 H 0.4569 0.7142 0.2622 0.032 Uiso 1 1 calc R U . . .
C2 C 0.36382(12) 0.56030(13) 0.36117(9) 0.0308(3) Uani 1 1 d . . . . .
H2 H 0.2797 0.5991 0.3559 0.037 Uiso 1 1 calc R U . . .
C3 C 0.38079(12) 0.43230(13) 0.42827(9) 0.0290(3) Uani 1 1 d . . . . .
H3 H 0.3089 0.3884 0.4710 0.035 Uiso 1 1 calc R U . . .
C4 C 0.49863(11) 0.37036(11) 0.43300(8) 0.0233(2) Uani 1 1 d . . . . .
C5 C 0.51147(11) 0.24228(12) 0.51400(8) 0.0244(2) Uani 1 1 d . . . . .
C6 C 0.68441(11) 0.16903(12) 0.42475(9) 0.0243(2) Uani 1 1 d . . . . .
H6A H 0.6175 0.1818 0.3742 0.029 Uiso 1 1 calc R U . . .
H6B H 0.7236 0.0829 0.4373 0.029 Uiso 1 1 calc R U . . .
C7 C 0.79136(11) 0.27212(11) 0.38307(8) 0.0216(2) Uani 1 1 d . . . . .
H7 H 0.8345 0.2568 0.3245 0.026 Uiso 1 1 calc R U . . .
C8 C 0.89857(11) 0.26175(11) 0.45642(8) 0.0217(2) Uani 1 1 d . . . . .
C9 C 0.99702(14) 0.17202(15) 0.46885(12) 0.0399(3) Uani 1 1 d . . . . .
H9 H 0.9987 0.1172 0.4307 0.048 Uiso 1 1 calc R U . . .
C10 C 1.09388(15) 0.16114(17) 0.53667(13) 0.0486(4) Uani 1 1 d . . . . .
H10 H 1.1608 0.0986 0.5446 0.058 Uiso 1 1 calc R U . . .
C11 C 1.09399(12) 0.24020(13) 0.59258(9) 0.0306(3) Uani 1 1 d . . . . .
H11 H 1.1595 0.2314 0.6396 0.037 Uiso 1 1 calc R U . . .
C12 C 0.99813(12) 0.33171(12) 0.57918(9) 0.0277(3) Uani 1 1 d . . . . .
H12 H 0.9977 0.3876 0.6165 0.033 Uiso 1 1 calc R U . . .
C13 C 0.90145(12) 0.34282(12) 0.51103(9) 0.0261(2) Uani 1 1 d . . . . .
H13 H 0.8362 0.4072 0.5018 0.031 Uiso 1 1 calc R U . . .
C14 C 0.73099(11) 0.40295(11) 0.34431(8) 0.0206(2) Uani 1 1 d . . . . .
C15 C 0.79006(11) 0.51561(11) 0.27162(8) 0.0211(2) Uani 1 1 d . . . . .
C16 C 0.91057(11) 0.53605(12) 0.21630(9) 0.0252(2) Uani 1 1 d . . . . .
H16 H 0.9736 0.4692 0.2288 0.030 Uiso 1 1 calc R U . . .
C17 C 0.93490(12) 0.65531(13) 0.14366(9) 0.0297(3) Uani 1 1 d . . . . .
H17 H 1.0149 0.6695 0.1046 0.036 Uiso 1 1 calc R U . . .
C18 C 0.84439(13) 0.75683(12) 0.12570(9) 0.0308(3) Uani 1 1 d . . . . .
H18 H 0.8652 0.8384 0.0760 0.037 Uiso 1 1 calc R U . . .
C19 C 0.72568(12) 0.73962(12) 0.17927(9) 0.0267(2) Uani 1 1 d . . . . .
H19 H 0.6642 0.8077 0.1675 0.032 Uiso 1 1 calc R U . . .
C20 C 0.70016(11) 0.61784(11) 0.25146(8) 0.0223(2) Uani 1 1 d . . . . .
C21 C 0.60646(11) 0.43662(11) 0.36696(8) 0.0207(2) Uani 1 1 d . . . . .
C22 C 0.61467(11) 0.51331(11) 0.08926(8) 0.0221(2) Uani 1 1 d . . . . .
H22 H 0.6979 0.5527 0.0645 0.027 Uiso 1 1 calc R U . . .
C23 C 0.50754(12) 0.58775(11) 0.08530(8) 0.0247(2) Uani 1 1 d . . . . .
H23 H 0.5162 0.6793 0.0606 0.030 Uiso 1 1 calc R U . . .
C24 C 0.38271(12) 0.52858(11) 0.11805(8) 0.0244(2) Uani 1 1 d . . . . .
H24 H 0.3073 0.5813 0.1119 0.029 Uiso 1 1 calc R U . . .
C25 C 0.36856(11) 0.39679(11) 0.15842(8) 0.0223(2) Uani 1 1 d . . . . .
C26 C 0.23198(12) 0.34388(12) 0.17362(9) 0.0259(2) Uani 1 1 d . . . . .
C27 C 0.29471(12) 0.14635(12) 0.30817(9) 0.0264(2) Uani 1 1 d . . . . .
H27A H 0.2451 0.0772 0.3613 0.032 Uiso 1 1 calc R U . . .
H27B H 0.3364 0.2024 0.3394 0.032 Uiso 1 1 calc R U . . .
C28 C 0.40185(11) 0.08496(11) 0.26261(8) 0.0216(2) Uani 1 1 d . . . . .
H28 H 0.4468 0.0204 0.3193 0.026 Uiso 1 1 calc R U . . .
C29 C 0.34322(11) 0.00985(11) 0.20255(8) 0.0213(2) Uani 1 1 d . . . . .
C30 C 0.24948(12) -0.08745(12) 0.24694(9) 0.0258(2) Uani 1 1 d . . . . .
H30 H 0.2236 -0.1082 0.3151 0.031 Uiso 1 1 calc R U . . .
C31 C 0.19350(12) -0.15433(12) 0.19260(9) 0.0285(3) Uani 1 1 d . . . . .
H31 H 0.1287 -0.2193 0.2236 0.034 Uiso 1 1 calc R U . . .
C32 C 0.23177(12) -0.12679(12) 0.09328(9) 0.0282(3) Uani 1 1 d . . . . .
H32 H 0.1937 -0.1728 0.0562 0.034 Uiso 1 1 calc R U . . .
C33 C 0.32562(13) -0.03191(12) 0.04898(9) 0.0301(3) Uani 1 1 d . . . . .
H33 H 0.3530 -0.0130 -0.0187 0.036 Uiso 1 1 calc R U . . .
C34 C 0.38056(12) 0.03638(12) 0.10314(9) 0.0271(3) Uani 1 1 d . . . . .
H34 H 0.4445 0.1020 0.0716 0.033 Uiso 1 1 calc R U . . .
C35 C 0.50303(11) 0.18558(11) 0.20675(8) 0.0202(2) Uani 1 1 d . . . . .
C36 C 0.63950(11) 0.16626(11) 0.18927(8) 0.0204(2) Uani 1 1 d . . . . .
C37 C 0.71815(11) 0.05524(11) 0.21446(9) 0.0239(2) Uani 1 1 d . . . . .
H37 H 0.6811 -0.0281 0.2494 0.029 Uiso 1 1 calc R U . . .
C38 C 0.85042(12) 0.07014(12) 0.18729(9) 0.0271(3) Uani 1 1 d . . . . .
H38 H 0.9044 -0.0042 0.2036 0.033 Uiso 1 1 calc R U . . .
C39 C 0.90719(11) 0.19277(12) 0.13601(9) 0.0266(2) Uani 1 1 d . . . . .
H39 H 0.9984 0.1994 0.1177 0.032 Uiso 1 1 calc R U . . .
C40 C 0.83289(11) 0.30409(12) 0.11160(8) 0.0234(2) Uani 1 1 d . . . . .
H40 H 0.8710 0.3871 0.0774 0.028 Uiso 1 1 calc R U . . .
C41 C 0.69932(11) 0.28849(11) 0.13966(8) 0.0205(2) Uani 1 1 d . . . . .
C42 C 0.48216(11) 0.31694(11) 0.16889(8) 0.0197(2) Uani 1 1 d . . . . .
N1 N 0.58649(9) 0.56912(9) 0.30914(7) 0.0216(2) Uani 1 1 d . . . . .
N2 N 0.60292(9) 0.38139(9) 0.12896(7) 0.01993(19) Uani 1 1 d . . . . .
O1 O 0.43080(9) 0.20165(9) 0.58233(7) 0.0337(2) Uani 1 1 d . . . . .
O2 O 0.62037(8) 0.17091(8) 0.51625(6) 0.02501(18) Uani 1 1 d . . . . .
O3 O 0.14296(9) 0.40705(9) 0.12743(8) 0.0358(2) Uani 1 1 d . . . . .
O4 O 0.20392(8) 0.22257(8) 0.23606(7) 0.02814(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3486(18) . ?
C1 N1 1.3645(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.4172(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3715(17) . ?
C3 H3 0.9500 . ?
C4 C21 1.4388(16) . ?
C4 C5 1.4905(16) . ?
C5 O1 1.2099(14) . ?
C5 O2 1.3533(14) . ?
C6 O2 1.4500(14) . ?
C6 C7 1.5219(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C14 1.4939(16) . ?
C7 C8 1.5255(15) . ?
C7 H7 1.0000 . ?
C8 C9 1.3795(17) . ?
C8 C13 1.3859(16) . ?
C9 C10 1.3910(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3725(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3925(17) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C21 1.3784(15) . ?
C14 C15 1.4271(16) . ?
C15 C20 1.4078(16) . ?
C15 C16 1.4080(16) . ?
C16 C17 1.3770(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.4080(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.3821(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.3957(17) . ?
C19 H19 0.9500 . ?
C20 N1 1.3876(15) . ?
C21 N1 1.4241(14) . ?
C22 C23 1.3549(17) . ?
C22 N2 1.3689(15) . ?
C22 H22 0.9500 . ?
C23 C24 1.4156(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3699(17) . ?
C24 H24 0.9500 . ?
C25 C42 1.4328(16) . ?
C25 C26 1.4884(16) . ?
C26 O3 1.2115(15) . ?
C26 O4 1.3473(15) . ?
C27 O4 1.4475(15) . ?
C27 C28 1.5260(16) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C35 1.5004(15) . ?
C28 C29 1.5317(15) . ?
C28 H28 1.0000 . ?
C29 C34 1.3895(16) . ?
C29 C30 1.3953(16) . ?
C30 C31 1.3899(17) . ?
C30 H30 0.9500 . ?
C31 C32 1.3889(18) . ?
C31 H31 0.9500 . ?
C32 C33 1.3796(18) . ?
C32 H32 0.9500 . ?
C33 C34 1.3948(17) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C42 1.3777(16) . ?
C35 C36 1.4306(15) . ?
C36 C37 1.4076(16) . ?
C36 C41 1.4120(16) . ?
C37 C38 1.3805(17) . ?
C37 H37 0.9500 . ?
C38 C39 1.4066(18) . ?
C38 H38 0.9500 . ?
C39 C40 1.3855(17) . ?
C39 H39 0.9500 . ?
C40 C41 1.3961(15) . ?
C40 H40 0.9500 . ?
C41 N2 1.3910(14) . ?
C42 N2 1.4170(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 119.95(11) . . ?
C2 C1 H1 120.0 . . ?
N1 C1 H1 120.0 . . ?
C1 C2 C3 119.94(11) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 121.52(12) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C21 118.95(11) . . ?
C3 C4 C5 117.42(11) . . ?
C21 C4 C5 123.33(10) . . ?
O1 C5 O2 117.61(11) . . ?
O1 C5 C4 122.32(11) . . ?
O2 C5 C4 119.93(10) . . ?
O2 C6 C7 113.34(9) . . ?
O2 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
O2 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C14 C7 C6 109.93(9) . . ?
C14 C7 C8 113.48(9) . . ?
C6 C7 C8 112.86(9) . . ?
C14 C7 H7 106.7 . . ?
C6 C7 H7 106.7 . . ?
C8 C7 H7 106.7 . . ?
C9 C8 C13 118.14(11) . . ?
C9 C8 C7 120.47(10) . . ?
C13 C8 C7 121.39(10) . . ?
C8 C9 C10 120.59(12) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.80(13) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.05(11) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 120.10(11) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 121.27(11) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C21 C14 C15 107.00(10) . . ?
C21 C14 C7 127.13(10) . . ?
C15 C14 C7 125.78(10) . . ?
C20 C15 C16 118.92(11) . . ?
C20 C15 C14 108.73(10) . . ?
C16 C15 C14 132.18(11) . . ?
C17 C16 C15 118.40(11) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C16 C17 C18 121.74(11) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 121.05(12) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 117.08(12) . . ?
C18 C19 H19 121.5 . . ?
C20 C19 H19 121.5 . . ?
N1 C20 C19 129.84(11) . . ?
N1 C20 C15 107.16(10) . . ?
C19 C20 C15 122.80(11) . . ?
C14 C21 N1 108.59(10) . . ?
C14 C21 C4 135.15(11) . . ?
N1 C21 C4 116.26(10) . . ?
C23 C22 N2 119.97(11) . . ?
C23 C22 H22 120.0 . . ?
N2 C22 H22 120.0 . . ?
C22 C23 C24 119.76(11) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 121.27(11) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C42 119.58(10) . . ?
C24 C25 C26 116.83(11) . . ?
C42 C25 C26 122.80(10) . . ?
O3 C26 O4 117.70(11) . . ?
O3 C26 C25 120.96(11) . . ?
O4 C26 C25 121.29(10) . . ?
O4 C27 C28 113.03(9) . . ?
O4 C27 H27A 109.0 . . ?
C28 C27 H27A 109.0 . . ?
O4 C27 H27B 109.0 . . ?
C28 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C35 C28 C27 109.56(9) . . ?
C35 C28 C29 115.06(9) . . ?
C27 C28 C29 111.38(9) . . ?
C35 C28 H28 106.8 . . ?
C27 C28 H28 106.8 . . ?
C29 C28 H28 106.8 . . ?
C34 C29 C30 118.15(10) . . ?
C34 C29 C28 121.54(10) . . ?
C30 C29 C28 120.30(10) . . ?
C31 C30 C29 120.81(11) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C32 C31 C30 120.40(11) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C33 C32 C31 119.27(11) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C32 C33 C34 120.33(11) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C29 C34 C33 121.02(11) . . ?
C29 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C42 C35 C36 107.05(10) . . ?
C42 C35 C28 125.33(10) . . ?
C36 C35 C28 127.46(10) . . ?
C37 C36 C41 118.86(10) . . ?
C37 C36 C35 132.93(11) . . ?
C41 C36 C35 108.17(10) . . ?
C38 C37 C36 118.50(11) . . ?
C38 C37 H37 120.7 . . ?
C36 C37 H37 120.7 . . ?
C37 C38 C39 121.55(11) . . ?
C37 C38 H38 119.2 . . ?
C39 C38 H38 119.2 . . ?
C40 C39 C38 121.35(11) . . ?
C40 C39 H39 119.3 . . ?
C38 C39 H39 119.3 . . ?
C39 C40 C41 116.85(11) . . ?
C39 C40 H40 121.6 . . ?
C41 C40 H40 121.6 . . ?
N2 C41 C40 129.66(10) . . ?
N2 C41 C36 107.46(9) . . ?
C40 C41 C36 122.86(11) . . ?
C35 C42 N2 109.05(10) . . ?
C35 C42 C25 134.46(10) . . ?
N2 C42 C25 116.42(10) . . ?
C1 N1 C20 128.19(10) . . ?
C1 N1 C21 122.74(10) . . ?
C20 N1 C21 108.51(9) . . ?
C22 N2 C41 129.02(10) . . ?
C22 N2 C42 122.74(10) . . ?
C41 N2 C42 108.23(9) . . ?
C5 O2 C6 120.69(9) . . ?
C26 O4 C27 122.74(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 3.07(19) . . . . ?
C1 C2 C3 C4 -4.42(19) . . . . ?
C2 C3 C4 C21 -1.05(18) . . . . ?
C2 C3 C4 C5 172.88(11) . . . . ?
C3 C4 C5 O1 -11.08(17) . . . . ?
C21 C4 C5 O1 162.56(11) . . . . ?
C3 C4 C5 O2 173.30(10) . . . . ?
C21 C4 C5 O2 -13.06(17) . . . . ?
O2 C6 C7 C14 -70.06(12) . . . . ?
O2 C6 C7 C8 57.73(12) . . . . ?
C14 C7 C8 C9 -154.24(12) . . . . ?
C6 C7 C8 C9 79.85(14) . . . . ?
C14 C7 C8 C13 24.69(15) . . . . ?
C6 C7 C8 C13 -101.22(13) . . . . ?
C13 C8 C9 C10 1.9(2) . . . . ?
C7 C8 C9 C10 -179.11(14) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -1.1(2) . . . . ?
C10 C11 C12 C13 0.9(2) . . . . ?
C9 C8 C13 C12 -2.14(19) . . . . ?
C7 C8 C13 C12 178.90(11) . . . . ?
C11 C12 C13 C8 0.76(19) . . . . ?
C6 C7 C14 C21 18.81(15) . . . . ?
C8 C7 C14 C21 -108.65(13) . . . . ?
C6 C7 C14 C15 -157.25(10) . . . . ?
C8 C7 C14 C15 75.30(13) . . . . ?
C21 C14 C15 C20 0.56(12) . . . . ?
C7 C14 C15 C20 177.27(10) . . . . ?
C21 C14 C15 C16 -174.43(11) . . . . ?
C7 C14 C15 C16 2.28(19) . . . . ?
C20 C15 C16 C17 -0.74(16) . . . . ?
C14 C15 C16 C17 173.84(11) . . . . ?
C15 C16 C17 C18 1.70(17) . . . . ?
C16 C17 C18 C19 -1.38(18) . . . . ?
C17 C18 C19 C20 0.05(17) . . . . ?
C18 C19 C20 N1 -173.22(11) . . . . ?
C18 C19 C20 C15 0.91(16) . . . . ?
C16 C15 C20 N1 174.71(9) . . . . ?
C14 C15 C20 N1 -1.05(12) . . . . ?
C16 C15 C20 C19 -0.57(16) . . . . ?
C14 C15 C20 C19 -176.33(10) . . . . ?
C15 C14 C21 N1 0.14(12) . . . . ?
C7 C14 C21 N1 -176.51(10) . . . . ?
C15 C14 C21 C4 -179.65(12) . . . . ?
C7 C14 C21 C4 3.7(2) . . . . ?
C3 C4 C21 C14 -172.91(12) . . . . ?
C5 C4 C21 C14 13.5(2) . . . . ?
C3 C4 C21 N1 7.31(15) . . . . ?
C5 C4 C21 N1 -166.24(10) . . . . ?
N2 C22 C23 C24 -2.93(16) . . . . ?
C22 C23 C24 C25 3.22(17) . . . . ?
C23 C24 C25 C42 0.72(16) . . . . ?
C23 C24 C25 C26 -169.39(10) . . . . ?
C24 C25 C26 O3 21.12(17) . . . . ?
C42 C25 C26 O3 -148.65(12) . . . . ?
C24 C25 C26 O4 -161.56(10) . . . . ?
C42 C25 C26 O4 28.68(16) . . . . ?
O4 C27 C28 C35 76.51(11) . . . . ?
O4 C27 C28 C29 -51.94(12) . . . . ?
C35 C28 C29 C34 -1.22(16) . . . . ?
C27 C28 C29 C34 124.23(12) . . . . ?
C35 C28 C29 C30 179.12(10) . . . . ?
C27 C28 C29 C30 -55.43(14) . . . . ?
C34 C29 C30 C31 -1.08(18) . . . . ?
C28 C29 C30 C31 178.60(11) . . . . ?
C29 C30 C31 C32 1.10(19) . . . . ?
C30 C31 C32 C33 -0.25(19) . . . . ?
C31 C32 C33 C34 -0.6(2) . . . . ?
C30 C29 C34 C33 0.24(18) . . . . ?
C28 C29 C34 C33 -179.43(11) . . . . ?
C32 C33 C34 C29 0.6(2) . . . . ?
C27 C28 C35 C42 -23.13(15) . . . . ?
C29 C28 C35 C42 103.26(12) . . . . ?
C27 C28 C35 C36 151.62(11) . . . . ?
C29 C28 C35 C36 -81.99(14) . . . . ?
C42 C35 C36 C37 177.08(11) . . . . ?
C28 C35 C36 C37 1.56(19) . . . . ?
C42 C35 C36 C41 -0.41(12) . . . . ?
C28 C35 C36 C41 -175.93(10) . . . . ?
C41 C36 C37 C38 -1.64(16) . . . . ?
C35 C36 C37 C38 -178.91(11) . . . . ?
C36 C37 C38 C39 0.31(17) . . . . ?
C37 C38 C39 C40 0.76(18) . . . . ?
C38 C39 C40 C41 -0.44(16) . . . . ?
C39 C40 C41 N2 177.16(10) . . . . ?
C39 C40 C41 C36 -0.96(16) . . . . ?
C37 C36 C41 N2 -176.46(9) . . . . ?
C35 C36 C41 N2 1.45(12) . . . . ?
C37 C36 C41 C40 2.02(16) . . . . ?
C35 C36 C41 C40 179.92(10) . . . . ?
C36 C35 C42 N2 -0.77(12) . . . . ?
C28 C35 C42 N2 174.87(9) . . . . ?
C36 C35 C42 C25 176.14(11) . . . . ?
C28 C35 C42 C25 -8.21(19) . . . . ?
C24 C25 C42 C35 178.65(12) . . . . ?
C26 C25 C42 C35 -11.86(19) . . . . ?
C24 C25 C42 N2 -4.61(15) . . . . ?
C26 C25 C42 N2 164.88(10) . . . . ?
C2 C1 N1 C20 174.16(11) . . . . ?
C2 C1 N1 C21 3.78(17) . . . . ?
C19 C20 N1 C1 4.49(19) . . . . ?
C15 C20 N1 C1 -170.35(10) . . . . ?
C19 C20 N1 C21 175.96(11) . . . . ?
C15 C20 N1 C21 1.13(11) . . . . ?
C14 C21 N1 C1 171.24(10) . . . . ?
C4 C21 N1 C1 -8.93(15) . . . . ?
C14 C21 N1 C20 -0.80(12) . . . . ?
C4 C21 N1 C20 179.04(9) . . . . ?
C23 C22 N2 C41 179.79(10) . . . . ?
C23 C22 N2 C42 -1.28(15) . . . . ?
C40 C41 N2 C22 -1.19(18) . . . . ?
C36 C41 N2 C22 177.14(10) . . . . ?
C40 C41 N2 C42 179.75(11) . . . . ?
C36 C41 N2 C42 -1.91(11) . . . . ?
C35 C42 N2 C22 -177.44(10) . . . . ?
C25 C42 N2 C22 5.02(14) . . . . ?
C35 C42 N2 C41 1.69(11) . . . . ?
C25 C42 N2 C41 -175.85(9) . . . . ?
O1 C5 O2 C6 147.68(11) . . . . ?
C4 C5 O2 C6 -36.50(15) . . . . ?
C7 C6 O2 C5 91.00(12) . . . . ?
O3 C26 O4 C27 -168.43(11) . . . . ?
C25 C26 O4 C27 14.16(16) . . . . ?
C28 C27 O4 C26 -79.68(13) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.043

