# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_T4ad
_database_code_depnum_ccdc_archive 'CCDC 2016844'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna'
;CSIR National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-12-17 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         ?
_chemical_formula_sum            'C24 H22 O'
_chemical_formula_weight         326.42

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                   9.9695(5)
_cell_length_b                   7.7193(4)
_cell_length_c                   22.7874(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.538(2)
_cell_angle_gamma                90
_cell_volume                     1718.22(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9248
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.11

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4158
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32959
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3351
_reflns_number_gt                3027
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1043P)²+1.9280P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         3351
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.2030
_refine_ls_wR_factor_gt          0.1981
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.7861(2) 0.5752(3) 0.53652(9) 0.0257(5) Uani 1 1 d . . . . .
C2 C 0.8464(2) 0.4122(3) 0.56474(9) 0.0295(5) Uani 1 1 d . . . . .
H2A H 0.8558 0.3298 0.5325 0.035 Uiso 1 1 calc R U . . .
H2B H 0.9396 0.4379 0.5875 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7704(2) 0.3265(3) 0.60493(9) 0.0277(5) Uani 1 1 d . . . . .
C4 C 0.6546(2) 0.3976(3) 0.61874(10) 0.0282(5) Uani 1 1 d . . . . .
H4 H 0.6120 0.3405 0.6471 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5916(2) 0.5658(3) 0.59005(9) 0.0249(5) Uani 1 1 d . . . . .
H5 H 0.5009 0.5323 0.5653 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6699(2) 0.6471(3) 0.54719(9) 0.0249(5) Uani 1 1 d . . . . .
C7 C 0.6072(2) 0.8034(3) 0.51324(10) 0.0314(5) Uani 1 1 d . . . . .
H7A H 0.6200 0.9057 0.5400 0.038 Uiso 1 1 calc R U . . .
H7B H 0.5076 0.7847 0.4994 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6738(3) 0.8371(3) 0.45909(11) 0.0387(6) Uani 1 1 d . . . . .
H8A H 0.6368 0.7549 0.4265 0.046 Uiso 1 1 calc R U . . .
H8B H 0.6522 0.9562 0.4440 0.046 Uiso 1 1 calc R U . . .
C9 C 0.8254(3) 0.8153(3) 0.47714(12) 0.0375(6) Uani 1 1 d . . . . .
H9A H 0.8683 0.8414 0.4425 0.045 Uiso 1 1 calc R U . . .
H9B H 0.8618 0.8985 0.5095 0.045 Uiso 1 1 calc R U . . .
C10 C 0.8240(3) 0.1564(3) 0.63121(11) 0.0353(6) Uani 1 1 d . . . . .
H10A H 0.7690 0.1174 0.6598 0.053 Uiso 1 1 calc R U . . .
H10B H 0.9196 0.1699 0.6518 0.053 Uiso 1 1 calc R U . . .
H10C H 0.8185 0.0705 0.5992 0.053 Uiso 1 1 calc R U . . .
C11 C 0.55971(19) 0.6958(3) 0.63692(8) 0.0199(4) Uani 1 1 d . . . . .
C12 C 0.66572(19) 0.7603(2) 0.68224(8) 0.0192(4) Uani 1 1 d . . . . .
C13 C 0.8075(2) 0.7162(3) 0.68652(9) 0.0215(4) Uani 1 1 d . . . . .
H13 H 0.8327 0.6427 0.6571 0.026 Uiso 1 1 calc R U . . .
C14 C 0.9064(2) 0.7770(3) 0.73174(9) 0.0243(5) Uani 1 1 d . . . . .
H14 H 0.9991 0.7452 0.7333 0.029 Uiso 1 1 calc R U . . .
C15 C 0.8735(2) 0.8873(3) 0.77662(10) 0.0274(5) Uani 1 1 d . . . . .
H15 H 0.9436 0.9279 0.8082 0.033 Uiso 1 1 calc R U . . .
C16 C 0.7414(2) 0.9346(3) 0.77428(9) 0.0267(5) Uani 1 1 d . . . . .
H16 H 0.7199 1.0090 0.8043 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6342(2) 0.8745(3) 0.72760(9) 0.0218(4) Uani 1 1 d . . . . .
C18 C 0.4995(2) 0.9254(3) 0.72530(9) 0.0236(5) Uani 1 1 d . . . . .
H18 H 0.4794 1.0025 0.7549 0.028 Uiso 1 1 calc R U . . .
C19 C 0.3937(2) 0.8657(3) 0.68068(9) 0.0212(4) Uani 1 1 d . . . . .
C20 C 0.2554(2) 0.9179(3) 0.67966(9) 0.0265(5) Uani 1 1 d . . . . .
H20 H 0.2369 0.9968 0.7091 0.032 Uiso 1 1 calc R U . . .
C21 C 0.1505(2) 0.8570(3) 0.63752(10) 0.0292(5) Uani 1 1 d . . . . .
H21 H 0.0593 0.8929 0.6375 0.035 Uiso 1 1 calc R U . . .
C22 C 0.1771(2) 0.7396(3) 0.59354(10) 0.0298(5) Uani 1 1 d . . . . .
H22 H 0.1030 0.6961 0.5644 0.036 Uiso 1 1 calc R U . . .
C23 C 0.3073(2) 0.6881(3) 0.59233(9) 0.0259(5) Uani 1 1 d . . . . .
H23 H 0.3220 0.6103 0.5619 0.031 Uiso 1 1 calc R U . . .
C24 C 0.42288(19) 0.7482(3) 0.63575(8) 0.0196(4) Uani 1 1 d . . . . .
O1 O 0.86112(16) 0.6410(2) 0.49780(7) 0.0322(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
C1 C6 1.350(3) . ?
C1 O1 1.363(3) . ?
C1 C2 1.484(3) . ?
C2 C3 1.459(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.370(3) . ?
C3 C10 1.497(3) . ?
C4 C5 1.531(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.504(3) . ?
C5 C11 1.544(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.500(3) . ?
C7 C8 1.536(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.495(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.446(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.412(3) . ?
C11 C24 1.418(3) . ?
C12 C13 1.438(3) . ?
C12 C17 1.440(3) . ?
C13 C14 1.359(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.419(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.357(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.426(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.432(3) . ?
C19 C24 1.441(3) . ?
C20 C21 1.355(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.415(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.363(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.437(3) . ?
C23 H23 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
C6 C1 O1 124.4(2) . . ?
C6 C1 C2 123.92(19) . . ?
O1 C1 C2 111.70(18) . . ?
C3 C2 C1 116.13(19) . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 C10 120.6(2) . . ?
C2 C3 C10 117.4(2) . . ?
C3 C4 C5 122.27(19) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 114.19(17) . . ?
C6 C5 C11 112.53(17) . . ?
C4 C5 C11 112.30(16) . . ?
C6 C5 H5 105.6 . . ?
C4 C5 H5 105.6 . . ?
C11 C5 H5 105.6 . . ?
C1 C6 C7 121.47(19) . . ?
C1 C6 C5 121.38(19) . . ?
C7 C6 C5 116.97(18) . . ?
C6 C7 C8 110.36(18) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C7 109.6(2) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O1 C9 C8 111.3(2) . . ?
O1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
O1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C24 119.31(17) . . ?
C12 C11 C5 120.47(17) . . ?
C24 C11 C5 120.20(17) . . ?
C11 C12 C13 123.21(17) . . ?
C11 C12 C17 120.12(17) . . ?
C13 C12 C17 116.66(17) . . ?
C14 C13 C12 121.56(19) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 121.11(19) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 119.71(19) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 121.21(19) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 120.68(18) . . ?
C18 C17 C12 119.58(18) . . ?
C16 C17 C12 119.74(18) . . ?
C19 C18 C17 121.36(18) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 120.41(18) . . ?
C18 C19 C24 119.82(18) . . ?
C20 C19 C24 119.76(19) . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 119.79(19) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 121.8(2) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C11 C24 C23 123.84(18) . . ?
C11 C24 C19 119.78(18) . . ?
C23 C24 C19 116.38(18) . . ?
C1 O1 C9 115.25(17) . . ?

_refine_diff_density_max         0.709
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_6im
_database_code_depnum_ccdc_archive 'CCDC 2016843'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna'
;CSIR National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2021-12-17 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         ?
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.2766(18)
_cell_length_b                   14.676(4)
_cell_length_c                   12.381(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.962(13)
_cell_angle_gamma                90
_cell_volume                     1293.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.16

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6561
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46945
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.861
_diffrn_reflns_theta_max         26.984
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5615
_reflns_number_gt                5525
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.991

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+5.4622P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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       0.066(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2538 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_chemical_absolute_configuration -
_refine_ls_number_reflns         5615
_refine_ls_number_parameters     362
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.2073
_refine_ls_wR_factor_gt          0.2070
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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 0.6017(8) 0.7336(5) 0.8198(5) 0.0136(12) Uani 1 1 d . . . . .
C2 C 0.6071(10) 0.6577(5) 0.9038(6) 0.0194(14) Uani 1 1 d . . . . .
H2A H 0.4816 0.6491 0.9215 0.023 Uiso 1 1 calc R U . . .
H2B H 0.6981 0.6723 0.9728 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6671(12) 0.5719(5) 0.8508(6) 0.0255(16) Uani 1 1 d . . . . .
H3A H 0.5652 0.5260 0.8398 0.031 Uiso 1 1 calc R U . . .
H3B H 0.7802 0.5451 0.8986 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7100(9) 0.6004(4) 0.7389(5) 0.0172(13) Uani 1 1 d . . . . .
H4 H 0.8475 0.5944 0.7408 0.021 Uiso 1 1 calc R U . . .
C5 C 0.5986(9) 0.5504(4) 0.6406(5) 0.0176(13) Uani 1 1 d . . . . .
H5A H 0.6344 0.4852 0.6453 0.021 Uiso 1 1 calc R U . . .
H5B H 0.4631 0.5545 0.6413 0.021 Uiso 1 1 calc R U . . .
C6 C 0.6401(9) 0.6817(4) 0.5336(5) 0.0139(12) Uani 1 1 d . . . . .
C7 C 0.6493(8) 0.7386(5) 0.6257(5) 0.0131(12) Uani 1 1 d . . . . .
C8 C 0.6628(8) 0.8334(4) 0.6105(5) 0.0126(12) Uani 1 1 d . . . . .
H8 H 0.6681 0.8734 0.6714 0.015 Uiso 1 1 calc R U . . .
C9 C 0.6684(8) 0.8684(4) 0.5079(5) 0.0137(12) Uani 1 1 d . . . . .
H9 H 0.6770 0.9325 0.4992 0.016 Uiso 1 1 calc R U . . .
C10 C 0.6615(8) 0.8112(4) 0.4160(5) 0.0126(12) Uani 1 1 d . . . . .
C11 C 0.6463(9) 0.7179(4) 0.4305(5) 0.0146(13) Uani 1 1 d . . . . .
H11 H 0.6400 0.6782 0.3692 0.018 Uiso 1 1 calc R U . . .
C12 C 0.6730(8) 0.8471(4) 0.3049(5) 0.0136(12) Uani 1 1 d . . . . .
C13 C 0.5645(9) 0.8066(5) 0.2097(5) 0.0149(12) Uani 1 1 d . . . . .
H13 H 0.4795 0.7590 0.2169 0.018 Uiso 1 1 calc R U . . .
C14 C 0.5808(9) 0.8360(5) 0.1049(5) 0.0182(13) Uani 1 1 d . . . . .
H14 H 0.5066 0.8083 0.0412 0.022 Uiso 1 1 calc R U . . .
C15 C 0.7046(10) 0.9053(5) 0.0931(5) 0.0175(13) Uani 1 1 d . . . . .
H15 H 0.7185 0.9241 0.0218 0.021 Uiso 1 1 calc R U . . .
C16 C 0.8089(10) 0.9473(5) 0.1878(5) 0.0182(13) Uani 1 1 d . . . . .
H16 H 0.8915 0.9959 0.1800 0.022 Uiso 1 1 calc R U . . .
C17 C 0.7940(9) 0.9194(4) 0.2924(5) 0.0150(12) Uani 1 1 d . . . . .
H17 H 0.8653 0.9490 0.3556 0.018 Uiso 1 1 calc R U . . .
C18 C 0.8822(9) 0.2811(5) 0.1885(5) 0.0152(13) Uani 1 1 d . . . . .
C19 C 0.8985(9) 0.3594(5) 0.1106(5) 0.0174(13) Uani 1 1 d . . . . .
H19A H 0.8181 0.3487 0.0368 0.021 Uiso 1 1 calc R U . . .
H19B H 1.0301 0.3673 0.1026 0.021 Uiso 1 1 calc R U . . .
C20 C 0.8313(9) 0.4424(5) 0.1660(5) 0.0170(13) Uani 1 1 d . . . . .
H20A H 0.6933 0.4495 0.1442 0.020 Uiso 1 1 calc R U . . .
H20B H 0.8925 0.4989 0.1475 0.020 Uiso 1 1 calc R U . . .
C21 C 0.8925(8) 0.4193(4) 0.2893(5) 0.0149(12) Uani 1 1 d . . . . .
H21 H 1.0254 0.4390 0.3175 0.018 Uiso 1 1 calc R U . . .
C22 C 0.7674(9) 0.4576(4) 0.3619(5) 0.0145(12) Uani 1 1 d . . . . .
H22A H 0.7739 0.5250 0.3621 0.017 Uiso 1 1 calc R U . . .
H22B H 0.6355 0.4394 0.3326 0.017 Uiso 1 1 calc R U . . .
C23 C 0.8425(8) 0.3299(4) 0.4790(5) 0.0122(12) Uani 1 1 d . . . . .
C24 C 0.8623(8) 0.2748(5) 0.3887(5) 0.0133(12) Uani 1 1 d . . . . .
C25 C 0.8740(8) 0.1806(4) 0.4049(5) 0.0131(12) Uani 1 1 d . . . . .
H25 H 0.8888 0.1421 0.3456 0.016 Uiso 1 1 calc R U . . .
C26 C 0.8643(8) 0.1423(4) 0.5062(5) 0.0130(12) Uani 1 1 d . . . . .
H26 H 0.8693 0.0779 0.5147 0.016 Uiso 1 1 calc R U . . .
C27 C 0.8475(9) 0.1970(4) 0.5953(5) 0.0132(12) Uani 1 1 d . . . . .
C28 C 0.8335(9) 0.2914(4) 0.5805(5) 0.0149(13) Uani 1 1 d . . . . .
H28 H 0.8179 0.3295 0.6400 0.018 Uiso 1 1 calc R U . . .
C29 C 0.8367(8) 0.1593(4) 0.7061(5) 0.0131(12) Uani 1 1 d . . . . .
C30 C 0.7250(9) 0.0834(4) 0.7157(5) 0.0151(12) Uani 1 1 d . . . . .
H30 H 0.6608 0.0531 0.6510 0.018 Uiso 1 1 calc R U . . .
C31 C 0.7065(9) 0.0515(4) 0.8195(5) 0.0149(12) Uani 1 1 d . . . . .
H31 H 0.6335 -0.0013 0.8253 0.018 Uiso 1 1 calc R U . . .
C32 C 0.7959(9) 0.0977(5) 0.9144(5) 0.0168(13) Uani 1 1 d . . . . .
H32 H 0.7803 0.0776 0.9849 0.020 Uiso 1 1 calc R U . . .
C33 C 0.9073(9) 0.1727(5) 0.9060(5) 0.0165(13) Uani 1 1 d . . . . .
H33 H 0.9693 0.2037 0.9707 0.020 Uiso 1 1 calc R U . . .
C34 C 0.9286(9) 0.2027(5) 0.8029(5) 0.0169(13) Uani 1 1 d . . . . .
H34 H 1.0069 0.2537 0.7980 0.020 Uiso 1 1 calc R U . . .
N1 N 0.6541(8) 0.6968(4) 0.7285(4) 0.0154(11) Uani 1 1 d . . . . .
N2 N 0.8798(7) 0.3188(4) 0.2904(4) 0.0134(11) Uani 1 1 d . . . . .
O1 O 0.5592(7) 0.8129(3) 0.8311(4) 0.0186(10) Uani 1 1 d . . . . .
O2 O 0.6317(7) 0.5879(3) 0.5392(4) 0.0173(10) Uani 1 1 d . . . . .
O3 O 0.8775(7) 0.1992(3) 0.1684(4) 0.0189(10) Uani 1 1 d . . . . .
O4 O 0.8285(7) 0.4236(3) 0.4729(3) 0.0160(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.220(8) . ?
C1 N1 1.375(8) . ?
C1 C2 1.519(9) . ?
C2 C3 1.525(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.540(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.471(8) . ?
C4 C5 1.507(9) . ?
C4 H4 1.0000 . ?
C5 O2 1.436(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O2 1.380(8) . ?
C6 C11 1.392(9) . ?
C6 C7 1.403(9) . ?
C7 N1 1.407(8) . ?
C7 C8 1.410(9) . ?
C8 C9 1.378(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.407(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(9) . ?
C10 C12 1.491(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.406(9) . ?
C12 C17 1.408(9) . ?
C13 C14 1.395(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.400(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 O3 1.227(8) . ?
C18 N2 1.381(8) . ?
C18 C19 1.520(9) . ?
C19 C20 1.527(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.537(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 N2 1.478(8) . ?
C21 C22 1.513(8) . ?
C21 H21 1.0000 . ?
C22 O4 1.443(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O4 1.380(7) . ?
C23 C28 1.392(9) . ?
C23 C24 1.411(9) . ?
C24 C25 1.396(9) . ?
C24 N2 1.407(8) . ?
C25 C26 1.390(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.398(9) . ?
C27 C29 1.497(8) . ?
C28 H28 0.9500 . ?
C29 C34 1.398(9) . ?
C29 C30 1.399(9) . ?
C30 C31 1.400(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.396(9) . ?
C31 H31 0.9500 . ?
C32 C33 1.384(9) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(9) . ?
C33 H33 0.9500 . ?
C34 H34 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
O1 C1 N1 126.1(6) . . ?
O1 C1 C2 126.3(6) . . ?
N1 C1 C2 107.7(6) . . ?
C1 C2 C3 106.2(5) . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C2 C3 C4 107.0(5) . . ?
C2 C3 H3A 110.3 . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3B 110.3 . . ?
C4 C3 H3B 110.3 . . ?
H3A C3 H3B 108.6 . . ?
N1 C4 C5 107.8(5) . . ?
N1 C4 C3 103.7(5) . . ?
C5 C4 C3 114.8(6) . . ?
N1 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
O2 C5 C4 111.1(5) . . ?
O2 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
O2 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
O2 C6 C11 115.9(5) . . ?
O2 C6 C7 123.2(6) . . ?
C11 C6 C7 120.9(6) . . ?
C6 C7 N1 117.7(6) . . ?
C6 C7 C8 118.1(5) . . ?
N1 C7 C8 124.1(6) . . ?
C9 C8 C7 120.5(6) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.3(6) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 118.3(6) . . ?
C11 C10 C12 119.2(6) . . ?
C9 C10 C12 122.4(6) . . ?
C10 C11 C6 120.9(6) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C13 C12 C17 118.8(6) . . ?
C13 C12 C10 119.6(6) . . ?
C17 C12 C10 121.6(6) . . ?
C14 C13 C12 120.5(6) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.5(6) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.0(6) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 121.3(6) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 119.8(6) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?
O3 C18 N2 125.0(6) . . ?
O3 C18 C19 127.9(6) . . ?
N2 C18 C19 107.1(6) . . ?
C18 C19 C20 104.1(5) . . ?
C18 C19 H19A 110.9 . . ?
C20 C19 H19A 110.9 . . ?
C18 C19 H19B 110.9 . . ?
C20 C19 H19B 110.9 . . ?
H19A C19 H19B 109.0 . . ?
C19 C20 C21 102.5(5) . . ?
C19 C20 H20A 111.3 . . ?
C21 C20 H20A 111.3 . . ?
C19 C20 H20B 111.3 . . ?
C21 C20 H20B 111.3 . . ?
H20A C20 H20B 109.2 . . ?
N2 C21 C22 108.6(5) . . ?
N2 C21 C20 102.9(5) . . ?
C22 C21 C20 114.9(5) . . ?
N2 C21 H21 110.0 . . ?
C22 C21 H21 110.0 . . ?
C20 C21 H21 110.0 . . ?
O4 C22 C21 109.4(5) . . ?
O4 C22 H22A 109.8 . . ?
C21 C22 H22A 109.8 . . ?
O4 C22 H22B 109.8 . . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
O4 C23 C28 115.9(5) . . ?
O4 C23 C24 123.1(5) . . ?
C28 C23 C24 121.0(6) . . ?
C25 C24 N2 124.4(6) . . ?
C25 C24 C23 117.8(6) . . ?
N2 C24 C23 117.6(6) . . ?
C26 C25 C24 121.2(6) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C27 120.7(6) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C28 119.0(6) . . ?
C26 C27 C29 122.9(6) . . ?
C28 C27 C29 118.1(6) . . ?
C23 C28 C27 120.3(6) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C34 C29 C30 118.3(6) . . ?
C34 C29 C27 120.7(6) . . ?
C30 C29 C27 120.9(6) . . ?
C29 C30 C31 120.8(6) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C32 C31 C30 119.6(6) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C33 C32 C31 120.1(6) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 120.0(6) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 C29 121.2(6) . . ?
C33 C34 H34 119.4 . . ?
C29 C34 H34 119.4 . . ?
C1 N1 C7 127.9(6) . . ?
C1 N1 C4 115.1(5) . . ?
C7 N1 C4 116.9(5) . . ?
C18 N2 C24 128.8(6) . . ?
C18 N2 C21 112.3(5) . . ?
C24 N2 C21 118.9(5) . . ?
C6 O2 C5 116.3(5) . . ?
C23 O4 C22 113.7(5) . . ?

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_5hm
_database_code_depnum_ccdc_archive 'CCDC 2016842'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna'
;CSIR National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2021-12-17 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         ?
_chemical_formula_sum            'C25 H26 O3'
_chemical_formula_weight         374.46

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                   14.6475(7)
_cell_length_b                   10.4651(5)
_cell_length_c                   13.6161(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.479(2)
_cell_angle_gamma                90
_cell_volume                     2029.69(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9686
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.11

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3929
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63797
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_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         3.038
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4351
_reflns_number_gt                3979
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0832P)²+0.4541P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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       0.40(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4351
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_restrained_S_all      1.216
_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 0.89816(8) 0.69060(11) 0.30884(9) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.90206(9) 0.69393(12) 0.42197(9) 0.0205(3) Uani 1 1 d . . . . .
H2A H 0.9675 0.7094 0.4597 0.025 Uiso 1 1 calc R U . . .
H2B H 0.8629 0.7655 0.4365 0.025 Uiso 1 1 calc R U . . .
C3 C 0.86708(8) 0.56890(12) 0.45809(9) 0.0195(3) Uani 1 1 d . . . . .
H3A H 0.9161 0.5024 0.4634 0.023 Uiso 1 1 calc R U . . .
H3B H 0.8549 0.5814 0.5260 0.023 Uiso 1 1 calc R U . . .
C4 C 0.77833(8) 0.52506(11) 0.38583(8) 0.0144(3) Uani 1 1 d . . . . .
C5 C 0.72016(8) 0.43163(11) 0.41277(8) 0.0137(3) Uani 1 1 d . . . . .
C6 C 0.63682(8) 0.39569(11) 0.34619(8) 0.0150(3) Uani 1 1 d . . . . .
H6 H 0.5986 0.3316 0.3656 0.018 Uiso 1 1 calc R U . . .
C7 C 0.60873(8) 0.45300(11) 0.25090(8) 0.0145(3) Uani 1 1 d . . . . .
C8 C 0.66652(8) 0.54489(11) 0.22355(8) 0.0151(3) Uani 1 1 d . . . . .
H8 H 0.6485 0.5848 0.1592 0.018 Uiso 1 1 calc R U . . .
C9 C 0.75049(8) 0.57907(11) 0.28940(9) 0.0148(3) Uani 1 1 d . . . . .
C10 C 0.95933(9) 0.58495(13) 0.28195(11) 0.0254(3) Uani 1 1 d . . . . .
H10A H 0.9376 0.5021 0.3010 0.038 Uiso 1 1 calc R U . . .
H10B H 1.0246 0.5985 0.3184 0.038 Uiso 1 1 calc R U . . .
H10C H 0.9552 0.5862 0.2091 0.038 Uiso 1 1 calc R U . . .
C11 C 0.92320(10) 0.81887(13) 0.27070(11) 0.0257(3) Uani 1 1 d . . . . .
H11A H 0.9177 0.8141 0.1977 0.038 Uiso 1 1 calc R U . . .
H11B H 0.9878 0.8411 0.3047 0.038 Uiso 1 1 calc R U . . .
H11C H 0.8803 0.8844 0.2851 0.038 Uiso 1 1 calc R U . . .
C12 C 0.51965(8) 0.41650(11) 0.17921(8) 0.0153(3) Uani 1 1 d . . . . .
C13 C 0.49103(8) 0.28858(12) 0.16828(9) 0.0192(3) Uani 1 1 d . . . . .
H13 H 0.5287 0.2245 0.2076 0.023 Uiso 1 1 calc R U . . .
C14 C 0.40799(9) 0.25447(13) 0.10042(9) 0.0231(3) Uani 1 1 d . . . . .
H14 H 0.3895 0.1673 0.0932 0.028 Uiso 1 1 calc R U . . .
C15 C 0.35212(9) 0.34767(14) 0.04324(9) 0.0243(3) Uani 1 1 d . . . . .
H15 H 0.2953 0.3244 -0.0028 0.029 Uiso 1 1 calc R U . . .
C16 C 0.37960(9) 0.47492(14) 0.05354(9) 0.0231(3) Uani 1 1 d . . . . .
H16 H 0.3415 0.5388 0.0146 0.028 Uiso 1 1 calc R U . . .
C17 C 0.46295(8) 0.50882(12) 0.12092(9) 0.0188(3) Uani 1 1 d . . . . .
H17 H 0.4815 0.5960 0.1273 0.023 Uiso 1 1 calc R U . . .
C18 C 0.74607(8) 0.37002(11) 0.51467(8) 0.0144(3) Uani 1 1 d . . . . .
C19 C 0.79480(8) 0.25400(11) 0.52901(8) 0.0157(3) Uani 1 1 d . . . . .
C20 C 0.81233(8) 0.19100(11) 0.62172(9) 0.0180(3) Uani 1 1 d . . . . .
H20 H 0.8439 0.1110 0.6302 0.022 Uiso 1 1 calc R U . . .
C21 C 0.78300(8) 0.24704(12) 0.70129(9) 0.0193(3) Uani 1 1 d . . . . .
H21 H 0.7948 0.2045 0.7646 0.023 Uiso 1 1 calc R U . . .
C22 C 0.73679(9) 0.36380(12) 0.69071(9) 0.0192(3) Uani 1 1 d . . . . .
H22 H 0.7182 0.4018 0.7464 0.023 Uiso 1 1 calc R U . . .
C23 C 0.71805(8) 0.42436(11) 0.59677(9) 0.0163(3) Uani 1 1 d . . . . .
C24 C 0.87066(9) 0.09073(13) 0.45446(10) 0.0244(3) Uani 1 1 d . . . . .
H24A H 0.9267 0.0955 0.5101 0.037 Uiso 1 1 calc R U . . .
H24B H 0.8893 0.0723 0.3913 0.037 Uiso 1 1 calc R U . . .
H24C H 0.8294 0.0226 0.4681 0.037 Uiso 1 1 calc R U . . .
C25 C 0.62991(10) 0.59039(14) 0.65206(11) 0.0280(3) Uani 1 1 d . . . . .
H25A H 0.5882 0.5264 0.6707 0.042 Uiso 1 1 calc R U . . .
H25B H 0.5935 0.6664 0.6253 0.042 Uiso 1 1 calc R U . . .
H25C H 0.6786 0.6139 0.7118 0.042 Uiso 1 1 calc R U . . .
O1 O 0.80179(6) 0.67000(8) 0.25366(6) 0.0194(2) Uani 1 1 d . . . . .
O2 O 0.82232(7) 0.20911(9) 0.44563(7) 0.0233(3) Uani 1 1 d . . . . .
O3 O 0.67281(7) 0.53880(9) 0.57698(7) 0.0230(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4522(14) . ?
C1 C11 1.5149(17) . ?
C1 C10 1.5206(18) . ?
C1 C2 1.5286(17) . ?
C2 C3 1.5276(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5074(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.4000(16) . ?
C4 C5 1.4009(16) . ?
C5 C6 1.3920(15) . ?
C5 C18 1.4965(15) . ?
C6 C7 1.4013(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3881(16) . ?
C7 C12 1.4859(15) . ?
C8 C9 1.3894(16) . ?
C8 H8 0.9500 . ?
C9 O1 1.3703(14) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.3948(17) . ?
C12 C13 1.4003(17) . ?
C13 C14 1.3917(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3914(17) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.3983(16) . ?
C18 C19 1.3989(16) . ?
C19 O2 1.3732(14) . ?
C19 C20 1.3939(16) . ?
C20 C21 1.3855(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.3880(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.3963(16) . ?
C22 H22 0.9500 . ?
C23 O3 1.3648(14) . ?
C24 O2 1.4180(15) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 O3 1.4252(15) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C11 103.77(10) . . ?
O1 C1 C10 108.88(10) . . ?
C11 C1 C10 111.00(11) . . ?
O1 C1 C2 109.16(9) . . ?
C11 C1 C2 111.73(10) . . ?
C10 C1 C2 111.93(10) . . ?
C3 C2 C1 111.61(10) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 110.70(10) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C9 C4 C5 117.73(10) . . ?
C9 C4 C3 120.51(10) . . ?
C5 C4 C3 121.75(10) . . ?
C6 C5 C4 120.84(10) . . ?
C6 C5 C18 118.81(10) . . ?
C4 C5 C18 120.35(10) . . ?
C5 C6 C7 120.73(10) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 118.63(10) . . ?
C8 C7 C12 119.93(10) . . ?
C6 C7 C12 121.44(10) . . ?
C7 C8 C9 120.57(10) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
O1 C9 C8 115.20(10) . . ?
O1 C9 C4 123.33(10) . . ?
C8 C9 C4 121.46(11) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.55(11) . . ?
C17 C12 C7 120.73(11) . . ?
C13 C12 C7 120.72(10) . . ?
C14 C13 C12 120.62(12) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.10(12) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.84(11) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.01(12) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.87(12) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C23 C18 C19 118.47(10) . . ?
C23 C18 C5 120.51(10) . . ?
C19 C18 C5 120.94(10) . . ?
O2 C19 C20 124.01(11) . . ?
O2 C19 C18 114.84(10) . . ?
C20 C19 C18 121.15(11) . . ?
C21 C20 C19 118.87(11) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 121.61(11) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C23 118.80(11) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
O3 C23 C22 124.19(11) . . ?
O3 C23 C18 114.74(10) . . ?
C22 C23 C18 121.07(11) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C9 O1 C1 117.82(9) . . ?
C19 O2 C24 117.76(10) . . ?
C23 O3 C25 117.76(10) . . ?

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.125

