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

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

data_UPS3218RKP_PT310A_0m
_database_code_depnum_ccdc_archive 'CCDC 1863166'
loop_
_audit_author_name
_audit_author_address
'Dr. Raghavaiah Pallepogu'
;Dr. Harisingh Gour University Sagar (M.P.)
India
;
_audit_update_record             
;
2018-08-21 deposited with the CCDC.	2019-03-27 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         'C34 H26 N2 O4, C H2 Cl2'
_chemical_formula_sum            'C35 H28 Cl2 N2 O4'
_chemical_formula_weight         611.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   11.156(5)
_cell_length_b                   11.456(5)
_cell_length_c                   13.201(6)
_cell_angle_alpha                100.51(2)
_cell_angle_beta                 108.58(2)
_cell_angle_gamma                100.45(2)
_cell_volume                     1519.5(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4828
_cell_measurement_theta_min      1.986
_cell_measurement_theta_max      28.697

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             636.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25896
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.684
_diffrn_reflns_theta_max         28.697
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             7505
_reflns_number_gt                4828
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_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)+(0.2000P)²] 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       0.041(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7505
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.1081
_refine_ls_wR_factor_ref         0.3861
_refine_ls_wR_factor_gt          0.3387
_refine_ls_goodness_of_fit_ref   1.474
_refine_ls_restrained_S_all      1.474
_refine_ls_shift/su_max          0.003
_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
N2 N 0.4675(3) 0.2852(2) -0.0602(2) 0.0438(6) Uani 1 1 d . . . . .
C1 C 0.2052(3) 0.0388(3) -0.2241(2) 0.0393(7) Uani 1 1 d . . . . .
C8 C 0.2589(3) 0.0566(3) -0.0127(2) 0.0339(6) Uani 1 1 d . . . . .
H8 H 0.3104 -0.0038 -0.0165 0.041 Uiso 1 1 calc R U . . .
C16 C 0.4705(3) 0.1993(3) -0.0008(2) 0.0368(6) Uani 1 1 d . . . . .
N1 N 0.2505(3) -0.0503(2) 0.2220(2) 0.0418(6) Uani 1 1 d . . . . .
C7 C 0.1595(3) 0.0406(3) -0.1289(2) 0.0371(6) Uani 1 1 d . . . . .
C14 C 0.4000(3) 0.1967(3) 0.1644(2) 0.0366(6) Uani 1 1 d . . . . .
H14 H 0.4545 0.1388 0.1774 0.044 Uiso 1 1 calc R U . . .
C9 C 0.1944(3) 0.0397(3) 0.0715(2) 0.0390(7) Uani 1 1 d . . . . .
H9 H 0.1044 0.0472 0.0426 0.047 Uiso 1 1 calc R U . . .
C13 C 0.2721(3) 0.1406(3) 0.1789(2) 0.0396(7) Uani 1 1 d . . . . .
H13 H 0.2239 0.2027 0.1885 0.048 Uiso 1 1 calc R U . . .
C15 C 0.3546(3) 0.1883(3) 0.0372(2) 0.0345(6) Uani 1 1 d . . . . .
C23 C 0.2954(3) 0.2879(3) -0.0026(2) 0.0398(7) Uani 1 1 d . . . . .
C10 C 0.1938(3) -0.0785(3) 0.1052(2) 0.0424(7) Uani 1 1 d . . . . .
C12 C 0.2908(3) 0.0757(3) 0.2707(3) 0.0449(7) Uani 1 1 d . . . . .
C24 C 0.2487(3) -0.1411(3) 0.2843(3) 0.0437(7) Uani 1 1 d . . . . .
C2 C 0.3074(3) -0.0107(3) -0.2299(3) 0.0471(8) Uani 1 1 d . . . . .
H2 H 0.3550 -0.0382 -0.1714 0.057 Uiso 1 1 calc R U . . .
C18 C 0.3653(3) 0.3392(3) -0.0626(3) 0.0426(7) Uani 1 1 d . . . . .
C29 C 0.3626(4) -0.1394(4) 0.3699(3) 0.0544(9) Uani 1 1 d . . . . .
H29 H 0.4407 -0.0818 0.3853 0.065 Uiso 1 1 calc R U . . .
C3 C 0.3378(4) -0.0188(4) -0.3238(3) 0.0636(11) Uani 1 1 d . . . . .
H3 H 0.4040 -0.0556 -0.3292 0.076 Uiso 1 1 calc R U . . .
C6 C 0.1401(4) 0.0835(4) -0.3115(3) 0.0581(10) Uani 1 1 d . . . . .
H6 H 0.0718 0.1182 -0.3079 0.070 Uiso 1 1 calc R U . . .
C22 C 0.1897(4) 0.3290(3) 0.0034(3) 0.0535(9) Uani 1 1 d . . . . .
H22 H 0.1409 0.2956 0.0415 0.064 Uiso 1 1 calc R U . . .
C28 C 0.3569(5) -0.2255(4) 0.4315(3) 0.0634(11) Uani 1 1 d . . . . .
H28 H 0.4316 -0.2245 0.4893 0.076 Uiso 1 1 calc R U . . .
C19 C 0.3316(4) 0.4300(3) -0.1147(3) 0.0606(10) Uani 1 1 d . . . . .
H19 H 0.3785 0.4617 -0.1549 0.073 Uiso 1 1 calc R U . . .
C25 C 0.1348(4) -0.2253(4) 0.2623(3) 0.0605(10) Uani 1 1 d . . . . .
H25 H 0.0587 -0.2256 0.2062 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2740(5) 0.0254(4) -0.4091(3) 0.0662(11) Uani 1 1 d . . . . .
H4 H 0.2978 0.0203 -0.4709 0.079 Uiso 1 1 calc R U . . .
C5 C 0.1743(5) 0.0774(4) -0.4026(3) 0.0694(12) Uani 1 1 d . . . . .
H5 H 0.1302 0.1084 -0.4599 0.083 Uiso 1 1 calc R U . . .
C21 C 0.1547(4) 0.4202(4) -0.0472(4) 0.0692(12) Uani 1 1 d . . . . .
H21 H 0.0827 0.4480 -0.0428 0.083 Uiso 1 1 calc R U . . .
C20 C 0.2280(5) 0.4705(4) -0.1049(4) 0.0718(13) Uani 1 1 d . . . . .
H20 H 0.2051 0.5329 -0.1371 0.086 Uiso 1 1 calc R U . . .
C27 C 0.2439(5) -0.3105(4) 0.4079(4) 0.0772(14) Uani 1 1 d . . . . .
H27 H 0.2417 -0.3685 0.4486 0.093 Uiso 1 1 calc R U . . .
C26 C 0.1330(5) -0.3112(5) 0.3246(5) 0.0831(15) Uani 1 1 d . . . . .
H26 H 0.0556 -0.3696 0.3092 0.100 Uiso 1 1 calc R U . . .
O3 O 0.5520(2) 0.1410(2) 0.0181(2) 0.0492(6) Uani 1 1 d . . . . .
O5 O 0.0463(2) 0.0328(3) -0.14466(19) 0.0550(7) Uani 1 1 d . . . . .
O1 O 0.3334(3) 0.1226(3) 0.36942(19) 0.0683(8) Uani 1 1 d . . . . .
O2 O 0.1527(3) -0.1806(2) 0.0460(2) 0.0626(8) Uani 1 1 d . . . . .
C30 C 0.5495(4) 0.3067(4) -0.1233(4) 0.0624(10) Uani 1 1 d . . . . .
H30A H 0.6155 0.2623 -0.1067 0.094 Uiso 1 1 calc R U . . .
H30B H 0.5906 0.3930 -0.1046 0.094 Uiso 1 1 calc R U . . .
H30C H 0.4972 0.2792 -0.2008 0.094 Uiso 1 1 calc R U . . .
C31 C 0.0653(10) 0.2992(18) 0.3290(10) 0.363(15) Uani 1 1 d . . . . .
H31A H 0.1399 0.3704 0.3580 0.436 Uiso 1 1 calc R U . . .
H31B H 0.0996 0.2272 0.3242 0.436 Uiso 1 1 calc R U . . .
Cl1 Cl -0.0160(2) 0.2994(3) 0.43575(18) 0.1477(9) Uani 1 1 d . . . . .
Cl2 Cl -0.0079(4) 0.3000(3) 0.2199(2) 0.1951(15) Uani 1 1 d . . . . .
C35 C 0.6168(4) 0.3449(3) 0.2793(3) 0.0566(9) Uani 1 1 d . . . . .
H35 H 0.6553 0.2851 0.2559 0.068 Uiso 1 1 calc R U . . .
C33 C 0.4826(3) 0.3202(3) 0.2424(3) 0.0448(8) Uani 1 1 d . . . . .
C32 C 0.4290(5) 0.4127(4) 0.2779(4) 0.0714(12) Uani 1 1 d . . . . .
H32 H 0.3386 0.3998 0.2544 0.086 Uiso 1 1 calc R U . . .
C34 C 0.5100(7) 0.5245(5) 0.3485(5) 0.0925(17) Uani 1 1 d . . . . .
H34 H 0.4733 0.5865 0.3707 0.111 Uiso 1 1 calc R U . . .
C36 C 0.6953(5) 0.4551(4) 0.3495(4) 0.0767(14) Uani 1 1 d . . . . .
H36 H 0.7858 0.4685 0.3724 0.092 Uiso 1 1 calc R U . . .
C37 C 0.6443(6) 0.5443(4) 0.3860(4) 0.0837(15) Uani 1 1 d . . . . .
H37 H 0.6984 0.6179 0.4355 0.100 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C16 1.365(4) . ?
N2 C18 1.387(4) . ?
N2 C30 1.440(5) . ?
C1 C2 1.379(4) . ?
C1 C6 1.392(4) . ?
C1 C7 1.498(4) . ?
C8 C9 1.527(4) . ?
C8 C7 1.535(4) . ?
C8 C15 1.567(4) . ?
C16 O3 1.213(4) . ?
C16 C15 1.522(4) . ?
N1 C12 1.393(4) . ?
N1 C10 1.416(4) . ?
N1 C24 1.440(4) . ?
C7 O5 1.196(4) . ?
C14 C33 1.517(4) . ?
C14 C13 1.540(4) . ?
C14 C15 1.570(4) . ?
C9 C10 1.499(4) . ?
C9 C13 1.533(4) . ?
C13 C12 1.513(4) . ?
C15 C23 1.513(4) . ?
C23 C22 1.366(5) . ?
C23 C18 1.406(5) . ?
C10 O2 1.197(4) . ?
C12 O1 1.213(4) . ?
C24 C25 1.359(5) . ?
C24 C29 1.400(5) . ?
C2 C3 1.378(5) . ?
C18 C19 1.391(4) . ?
C29 C28 1.393(6) . ?
C3 C4 1.363(5) . ?
C6 C5 1.367(5) . ?
C22 C21 1.388(5) . ?
C28 C27 1.352(7) . ?
C19 C20 1.355(6) . ?
C25 C26 1.394(5) . ?
C4 C5 1.373(6) . ?
C21 C20 1.403(7) . ?
C27 C26 1.366(7) . ?
C31 Cl2 1.413(14) . ?
C31 Cl1 1.904(16) . ?
C35 C36 1.370(6) . ?
C35 C33 1.374(5) . ?
C33 C32 1.388(5) . ?
C32 C34 1.390(7) . ?
C34 C37 1.379(9) . ?
C36 C37 1.344(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N2 C18 111.3(3) . . ?
C16 N2 C30 124.3(3) . . ?
C18 N2 C30 124.0(3) . . ?
C2 C1 C6 118.8(3) . . ?
C2 C1 C7 121.6(3) . . ?
C6 C1 C7 119.6(3) . . ?
C9 C8 C7 112.9(2) . . ?
C9 C8 C15 104.6(2) . . ?
C7 C8 C15 112.8(2) . . ?
O3 C16 N2 125.5(3) . . ?
O3 C16 C15 125.7(3) . . ?
N2 C16 C15 108.8(2) . . ?
C12 N1 C10 112.5(2) . . ?
C12 N1 C24 123.3(3) . . ?
C10 N1 C24 123.6(3) . . ?
O5 C7 C1 119.1(3) . . ?
O5 C7 C8 121.3(3) . . ?
C1 C7 C8 119.6(2) . . ?
C33 C14 C13 117.3(3) . . ?
C33 C14 C15 116.8(2) . . ?
C13 C14 C15 103.1(2) . . ?
C10 C9 C8 115.3(3) . . ?
C10 C9 C13 104.9(2) . . ?
C8 C9 C13 108.5(2) . . ?
C12 C13 C9 105.5(3) . . ?
C12 C13 C14 114.1(2) . . ?
C9 C13 C14 104.5(2) . . ?
C23 C15 C16 101.8(2) . . ?
C23 C15 C8 113.8(2) . . ?
C16 C15 C8 111.7(2) . . ?
C23 C15 C14 117.7(2) . . ?
C16 C15 C14 110.9(2) . . ?
C8 C15 C14 101.3(2) . . ?
C22 C23 C18 118.1(3) . . ?
C22 C23 C15 133.5(3) . . ?
C18 C23 C15 108.2(3) . . ?
O2 C10 N1 124.2(3) . . ?
O2 C10 C9 127.4(3) . . ?
N1 C10 C9 108.3(3) . . ?
O1 C12 N1 124.9(3) . . ?
O1 C12 C13 127.3(3) . . ?
N1 C12 C13 107.8(3) . . ?
C25 C24 C29 120.3(3) . . ?
C25 C24 N1 119.6(3) . . ?
C29 C24 N1 120.0(3) . . ?
C3 C2 C1 118.8(3) . . ?
N2 C18 C19 127.7(3) . . ?
N2 C18 C23 109.6(3) . . ?
C19 C18 C23 122.7(3) . . ?
C28 C29 C24 118.9(4) . . ?
C4 C3 C2 122.2(4) . . ?
C5 C6 C1 121.3(3) . . ?
C23 C22 C21 120.3(4) . . ?
C27 C28 C29 120.6(4) . . ?
C20 C19 C18 117.6(4) . . ?
C24 C25 C26 119.4(4) . . ?
C3 C4 C5 119.1(4) . . ?
C6 C5 C4 119.7(3) . . ?
C22 C21 C20 119.9(4) . . ?
C19 C20 C21 121.4(3) . . ?
C28 C27 C26 120.2(4) . . ?
C27 C26 C25 120.7(5) . . ?
Cl2 C31 Cl1 119.8(6) . . ?
C36 C35 C33 121.9(4) . . ?
C35 C33 C32 117.2(4) . . ?
C35 C33 C14 119.8(3) . . ?
C32 C33 C14 122.9(3) . . ?
C33 C32 C34 120.2(5) . . ?
C37 C34 C32 120.7(5) . . ?
C37 C36 C35 121.3(5) . . ?
C36 C37 C34 118.6(4) . . ?

_refine_diff_density_max         1.397
_refine_diff_density_min         -1.137
_refine_diff_density_rms         0.165

####################################################################### 
# 
# 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_ups3392rkp_pt02_0ma
_database_code_depnum_ccdc_archive 'CCDC 1890831'
loop_
_audit_author_name
_audit_author_address
'Piyush Tehri'
;IIT Roorkee
India
;
_audit_update_record             
;
2019-01-14 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H24 Cl N O3'
_chemical_formula_sum            'C32 H24 Cl N O3'
_chemical_formula_weight         505.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_symmetry_cell_setting           ?
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6788(6)
_cell_length_b                   11.5046(3)
_cell_length_c                   12.2981(3)
_cell_angle_alpha                114.4170(10)
_cell_angle_beta                 103.953(2)
_cell_angle_gamma                96.855(2)
_cell_volume                     1293.50(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4660
_cell_measurement_theta_min      1.92
_cell_measurement_theta_max      28.350

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             663
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20574
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         28.35
_reflns_number_total             6421
_reflns_number_gt                4660
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1174P)²+0.0503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6421
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1803
_refine_ls_wR_factor_gt          0.1407
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.61210(6) 0.41289(6) 1.06348(5) 0.0678(2) Uani 1 1 d . . .
C2 C 0.44872(17) 0.17691(16) 0.22867(16) 0.0440(4) Uani 1 1 d . . .
C3 C 0.45313(19) 0.1393(2) 0.10769(18) 0.0550(5) Uani 1 1 d . . .
H3 H 0.5217 0.1031 0.0847 0.066 Uiso 1 1 calc R . .
C5 C 0.2543(2) 0.2063(2) 0.0527(2) 0.0637(6) Uani 1 1 d . . .
H5 H 0.1887 0.2155 -0.0063 0.076 Uiso 1 1 calc R . .
C4 C 0.3568(2) 0.1547(2) 0.0205(2) 0.0625(5) Uani 1 1 d . . .
H4 H 0.3616 0.1301 -0.0603 0.075 Uiso 1 1 calc R . .
C1 C 0.3459(2) 0.2307(2) 0.2603(2) 0.0680(6) Uani 1 1 d . . .
H1 H 0.3419 0.2582 0.3416 0.082 Uiso 1 1 calc R . .
C6 C 0.2490(3) 0.2440(3) 0.1720(2) 0.0789(7) Uani 1 1 d . . .
H6 H 0.1795 0.2790 0.1940 0.095 Uiso 1 1 calc R . .
C26 C 0.92811(16) 0.08361(15) 0.64341(15) 0.0392(3) Uani 1 1 d . . .
H26 H 0.9937 0.0964 0.7154 0.047 Uiso 1 1 calc R . .
C25 C 0.99385(15) 0.32230(14) 0.74579(15) 0.0366(3) Uani 1 1 d . . .
C24 C 0.90847(15) 0.19525(14) 0.64064(14) 0.0353(3) Uani 1 1 d . . .
C9 C 0.66561(15) 0.19002(14) 0.54361(15) 0.0367(3) Uani 1 1 d . . .
H9 H 0.6380 0.0941 0.5091 0.044 Uiso 1 1 calc R . .
C23 C 0.81388(15) 0.22354(14) 0.54759(14) 0.0353(3) Uani 1 1 d . . .
H23 H 0.8205 0.1744 0.4633 0.042 Uiso 1 1 calc R . .
C17 C 1.02829(15) 0.55894(15) 0.78754(15) 0.0382(3) Uani 1 1 d . . .
C27 C 0.86514(16) -0.05484(15) 0.55383(16) 0.0402(4) Uani 1 1 d . . .
C8 C 0.56796(17) 0.22683(16) 0.45722(16) 0.0437(4) Uani 1 1 d . . .
H8A H 0.4813 0.2107 0.4674 0.052 Uiso 1 1 calc R . .
H8B H 0.5971 0.3206 0.4851 0.052 Uiso 1 1 calc R . .
C10 C 0.65246(15) 0.24787(15) 0.67460(15) 0.0370(3) Uani 1 1 d . . .
C13 C 0.62629(16) 0.34916(18) 0.91343(16) 0.0450(4) Uani 1 1 d . . .
C28 C 0.77725(18) -0.10082(17) 0.43198(17) 0.0478(4) Uani 1 1 d . . .
H28 H 0.7547 -0.0409 0.4027 0.057 Uiso 1 1 calc R . .
C7 C 0.55204(16) 0.15474(15) 0.31881(15) 0.0406(4) Uani 1 1 d . . .
C22 C 0.86717(16) 0.36997(15) 0.59497(15) 0.0391(3) Uani 1 1 d . . .
C18 C 1.02415(17) 0.61981(16) 0.90918(17) 0.0438(4) Uani 1 1 d . . .
H18 H 0.9828 0.5717 0.9413 0.053 Uiso 1 1 calc R . .
C11 C 0.62327(17) 0.16610(16) 0.72687(16) 0.0444(4) Uani 1 1 d . . .
H11 H 0.6126 0.0759 0.6811 0.053 Uiso 1 1 calc R . .
C15 C 0.66606(18) 0.38217(16) 0.74494(17) 0.0471(4) Uani 1 1 d . . .
H15 H 0.6828 0.4387 0.7108 0.057 Uiso 1 1 calc R . .
C14 C 0.65504(19) 0.43298(17) 0.86475(17) 0.0498(4) Uani 1 1 d . . .
H14 H 0.6670 0.5232 0.9118 0.060 Uiso 1 1 calc R . .
C12 C 0.60966(18) 0.21579(18) 0.84550(17) 0.0484(4) Uani 1 1 d . . .
H12 H 0.5895 0.1595 0.8790 0.058 Uiso 1 1 calc R . .
C32 C 0.8982(2) -0.14909(17) 0.59258(19) 0.0520(4) Uani 1 1 d . . .
H32 H 0.9578 -0.1212 0.6726 0.062 Uiso 1 1 calc R . .
C16 C 1.08991(18) 0.62911(18) 0.73815(19) 0.0499(4) Uani 1 1 d . . .
H16 H 1.0935 0.5875 0.6565 0.060 Uiso 1 1 calc R . .
C29 C 0.7237(2) -0.23336(18) 0.3550(2) 0.0583(5) Uani 1 1 d . . .
H29 H 0.6650 -0.2622 0.2744 0.070 Uiso 1 1 calc R . .
C31 C 0.8445(2) -0.28202(18) 0.5149(2) 0.0626(5) Uani 1 1 d . . .
H31 H 0.8676 -0.3430 0.5425 0.075 Uiso 1 1 calc R . .
C19 C 1.08202(19) 0.75269(18) 0.98250(19) 0.0560(5) Uani 1 1 d . . .
H19 H 1.0804 0.7941 1.0649 0.067 Uiso 1 1 calc R . .
C21 C 1.1464(2) 0.7640(2) 0.8146(2) 0.0643(6) Uani 1 1 d . . .
H21 H 1.1875 0.8131 0.7831 0.077 Uiso 1 1 calc R . .
C30 C 0.7563(2) -0.32404(18) 0.3960(2) 0.0634(5) Uani 1 1 d . . .
H30 H 0.7187 -0.4135 0.3435 0.076 Uiso 1 1 calc R . .
C20 C 1.1421(2) 0.82469(19) 0.9350(2) 0.0646(6) Uani 1 1 d . . .
H20 H 1.1798 0.9146 0.9848 0.077 Uiso 1 1 calc R . .
O3 O 1.07440(12) 0.34308(11) 0.84336(11) 0.0492(3) Uani 1 1 d . . .
O1 O 0.62065(13) 0.07960(12) 0.28053(12) 0.0530(3) Uani 1 1 d . . .
O2 O 0.82873(13) 0.43443(12) 0.54276(13) 0.0549(3) Uani 1 1 d . . .
N1 N 0.96609(13) 0.42080(12) 0.71045(12) 0.0370(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
Cl1 C13 1.7344(17) . ?
C2 C1 1.382(3) . ?
C2 C3 1.382(3) . ?
C2 C7 1.491(2) . ?
C3 C4 1.382(3) . ?
C5 C6 1.365(3) . ?
C5 C4 1.370(3) . ?
C1 C6 1.381(3) . ?
C26 C24 1.339(2) . ?
C26 C27 1.463(2) . ?
C25 O3 1.2054(19) . ?
C25 N1 1.4094(18) . ?
C25 C24 1.480(2) . ?
C24 C23 1.505(2) . ?
C9 C10 1.517(2) . ?
C9 C8 1.529(2) . ?
C9 C23 1.568(2) . ?
C23 C22 1.517(2) . ?
C17 C18 1.380(2) . ?
C17 C16 1.387(2) . ?
C17 N1 1.4368(19) . ?
C27 C28 1.398(2) . ?
C27 C32 1.402(2) . ?
C8 C7 1.508(2) . ?
C10 C11 1.386(2) . ?
C10 C15 1.392(2) . ?
C13 C14 1.370(3) . ?
C13 C12 1.374(3) . ?
C28 C29 1.373(2) . ?
C7 O1 1.2192(19) . ?
C22 O2 1.2125(18) . ?
C22 N1 1.385(2) . ?
C18 C19 1.378(2) . ?
C11 C12 1.382(2) . ?
C15 C14 1.384(2) . ?
C32 C31 1.378(3) . ?
C16 C21 1.397(3) . ?
C29 C30 1.379(3) . ?
C31 C30 1.379(3) . ?
C19 C20 1.376(3) . ?
C21 C20 1.367(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C3 118.34(17) . . ?
C1 C2 C7 122.48(16) . . ?
C3 C2 C7 119.16(16) . . ?
C2 C3 C4 120.76(19) . . ?
C6 C5 C4 119.60(18) . . ?
C5 C4 C3 120.18(19) . . ?
C6 C1 C2 120.5(2) . . ?
C5 C6 C1 120.6(2) . . ?
C24 C26 C27 131.71(15) . . ?
O3 C25 N1 124.28(14) . . ?
O3 C25 C24 129.07(13) . . ?
N1 C25 C24 106.64(12) . . ?
C26 C24 C25 118.51(14) . . ?
C26 C24 C23 133.15(15) . . ?
C25 C24 C23 108.33(12) . . ?
C10 C9 C8 110.53(12) . . ?
C10 C9 C23 111.96(12) . . ?
C8 C9 C23 114.46(13) . . ?
C24 C23 C22 102.78(12) . . ?
C24 C23 C9 112.95(12) . . ?
C22 C23 C9 111.67(12) . . ?
C18 C17 C16 121.16(15) . . ?
C18 C17 N1 119.23(13) . . ?
C16 C17 N1 119.61(15) . . ?
C28 C27 C32 117.45(15) . . ?
C28 C27 C26 125.38(14) . . ?
C32 C27 C26 117.16(16) . . ?
C7 C8 C9 115.76(13) . . ?
C11 C10 C15 117.82(15) . . ?
C11 C10 C9 120.09(14) . . ?
C15 C10 C9 122.08(13) . . ?
C14 C13 C12 120.94(16) . . ?
C14 C13 Cl1 119.38(14) . . ?
C12 C13 Cl1 119.68(13) . . ?
C29 C28 C27 120.79(16) . . ?
O1 C7 C2 120.37(15) . . ?
O1 C7 C8 121.49(14) . . ?
C2 C7 C8 118.13(14) . . ?
O2 C22 N1 124.57(15) . . ?
O2 C22 C23 126.27(15) . . ?
N1 C22 C23 109.14(12) . . ?
C19 C18 C17 119.25(16) . . ?
C12 C11 C10 121.40(15) . . ?
C14 C15 C10 121.11(15) . . ?
C13 C14 C15 119.41(16) . . ?
C13 C12 C11 119.29(15) . . ?
C31 C32 C27 121.56(18) . . ?
C17 C16 C21 118.13(18) . . ?
C28 C29 C30 120.64(19) . . ?
C32 C31 C30 119.54(17) . . ?
C20 C19 C18 120.6(2) . . ?
C20 C21 C16 120.86(18) . . ?
C31 C30 C29 120.00(18) . . ?
C21 C20 C19 119.96(18) . . ?
C22 N1 C25 112.21(12) . . ?
C22 N1 C17 123.56(12) . . ?
C25 N1 C17 124.16(13) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.129
