# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_3ca
_database_code_depnum_ccdc_archive 'CCDC 1872814'
loop_
_audit_author_name
_audit_author_address
'Jose Martin-Alvarez'
;University of Valladolid
Spain
;
_audit_update_record             
;
2020-10-26 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;
_audit_creation_date             2018-02-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 N O3'
_chemical_formula_sum            'C18 H13 N O3'
_chemical_formula_weight         291.29
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H13 N1 O3'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.3533(2)
_cell_length_b                   5.06800(10)
_cell_length_c                   13.1835(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.957(2)
_cell_angle_gamma                90
_cell_volume                     742.10(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5132
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      74.9790
_cell_measurement_theta_min      3.9350
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             304
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0558
0 0 1 0.0558
2 -3 2 0.1017
-2 3 -2 0.1017
5 0 -1 0.0178
-5 0 1 0.0418

_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 0.0000 -1.0000 -0.0121 -0.1186 0.0067
-0.0000 -0.0000 1.0000 0.0121 0.1186 -0.0067
2.0000 -3.0000 1.9999 0.0897 0.3407 0.9322
-2.0000 3.0000 -1.9999 -0.0897 -0.3407 -0.9322
5.0000 0.0000 -1.0000 0.6603 -0.0346 0.1544
-5.0000 -0.0000 1.0000 -0.6603 0.0346 -0.1544

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13704
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.597
_diffrn_reflns_theta_min         3.427
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -17.00   1.00    1.43    --  -40.93 -37.00  60.00   98
  2  ω   -117.00  -8.00   1.00    1.43    --  -40.93 -77.00 120.00  109
  3  ω    -65.00  34.00   1.00    1.43    --  -40.93  37.00 150.00   99
  4  ω   -115.00 -17.00   1.00    1.43    --  -40.93 -37.00 150.00   98
  5  ω   -113.00 -13.00   1.00    1.43    --  -40.93 -57.00 150.00  100
  6  ω      1.00  82.00   1.00    1.43    --   40.93 -99.00  30.00   81
  7  ω     29.00 109.00   1.00    5.70    --  111.26 -94.00-180.00   80
  8  ω     82.00 178.00   1.00    5.70    --  111.26  61.00 120.00   96
  9  ω     38.00 137.00   1.00    5.70    --  111.26 -45.00 -60.00   99
 10  ω     85.00 178.00   1.00    5.70    --  111.26  45.00  90.00   93
 11  ω     79.00 178.00   1.00    5.70    --  111.26  77.00-150.00   99
 12  ω     79.00 178.00   1.00    5.70    --  111.26  77.00 120.00   99
 13  ω     82.00 178.00   1.00    5.70    --  111.26  61.00-180.00   96
 14  ω     79.00 178.00   1.00    5.70    --  111.26  77.00 150.00   99
 15  ω     82.00 178.00   1.00    5.70    --  111.26  61.00-120.00   96
 16  ω     79.00 178.00   1.00    5.70    --  111.26  77.00  90.00   99
 17  ω     79.00 178.00   1.00    5.70    --  111.26  77.00-180.00   99
 18  ω     82.00 178.00   1.00    5.70    --  111.26  61.00  90.00   96
 19  ω     85.00 178.00   1.00    5.70    --  111.26  45.00-120.00   93
 20  ω     94.00 178.00   1.00    5.70    --  111.26 125.00  60.00   84
 21  ω     85.00 178.00   1.00    5.70    --  111.26  45.00 150.00   93
 22  ω     82.00 178.00   1.00    5.70    --  111.26  61.00 150.00   96
 23  ω     29.00 109.00   1.00    5.70    --  111.26 -94.00-120.00   80
 24  ω     85.00 178.00   1.00    5.70    --  111.26  45.00-180.00   93
 25  ω     85.00 178.00   1.00    5.70    --  111.26  45.00-150.00   93
 26  ω     85.00 178.00   1.00    5.70    --  111.26  45.00 120.00   93
 27  ω     83.00 178.00   1.00    5.70    --  111.26  30.00-120.00   95
 28  ω     81.00 178.00   1.00    5.70    --  111.26  65.00-152.83   97
 29  ω     82.00 178.00   1.00    5.70    --  111.26  60.00 155.75   96
 30  ω   -128.00 -34.00   1.00    1.43    --  -40.93 178.00 120.00   94
 31  ω   -113.00 -13.00   1.00    1.43    --  -40.93 -57.00 -30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1344772000
_diffrn_orient_matrix_UB_12      0.0678050000
_diffrn_orient_matrix_UB_13      0.0121007000
_diffrn_orient_matrix_UB_21      0.0168054000
_diffrn_orient_matrix_UB_22      -0.0233192000
_diffrn_orient_matrix_UB_23      0.1185900000
_diffrn_orient_matrix_UB_31      0.0295365000
_diffrn_orient_matrix_UB_32      -0.2955072000
_diffrn_orient_matrix_UB_33      -0.0066767000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    0.886
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                2637
_reflns_number_total             2887
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 1001 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(13)
_refine_ls_extinction_coef       0.0053(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+0.0507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0893
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.03248(16) 0.1341(5) 0.40080(17) 0.0884(6) Uani 1 1 d . . . . .
O2 O 0.37265(12) 0.4488(4) 0.51657(10) 0.0609(4) Uani 1 1 d . . . . .
O3 O 0.37443(12) 0.9390(4) 0.39963(13) 0.0624(4) Uani 1 1 d . . . . .
H3 H 0.4446 0.9293 0.4311 0.094 Uiso 1 1 calc GR . . . .
N1 N 0.18922(13) 0.4087(4) 0.39913(13) 0.0522(4) Uani 1 1 d . . . . .
C1 C 0.13781(16) 0.5385(5) 0.30356(15) 0.0538(5) Uani 1 1 d . . . . .
C2 C 0.21938(17) 0.7162(5) 0.27797(15) 0.0551(5) Uani 1 1 d . . . . .
C3 C 0.1899(2) 0.8796(7) 0.19308(17) 0.0711(7) Uani 1 1 d . . . . .
H3A H 0.2447 1.0024 0.1780 0.085 Uiso 1 1 calc R . . . .
C4 C 0.0752(3) 0.8549(8) 0.13040(19) 0.0829(10) Uani 1 1 d . . . . .
H4 H 0.0525 0.9615 0.0722 0.099 Uiso 1 1 calc R . . . .
C5 C -0.0043(2) 0.6723(7) 0.15493(18) 0.0792(9) Uani 1 1 d . . . . .
H5 H -0.0799 0.6568 0.1116 0.095 Uiso 1 1 calc R . . . .
C6 C 0.02347(19) 0.5108(6) 0.24135(18) 0.0678(7) Uani 1 1 d . . . . .
H6 H -0.0316 0.3897 0.2570 0.081 Uiso 1 1 calc R . . . .
C7 C 0.30668(15) 0.5009(4) 0.43505(14) 0.0494(5) Uani 1 1 d . . . . .
C8 C 0.33793(16) 0.6939(5) 0.35357(15) 0.0511(5) Uani 1 1 d . . . . .
C9 C 0.12855(19) 0.2151(5) 0.4469(2) 0.0631(6) Uani 1 1 d . . . . .
C10 C 0.1848(3) 0.1238(8) 0.5522(2) 0.0835(9) Uani 1 1 d . . . . .
H10A H 0.1831 0.2636 0.6010 0.125 Uiso 1 1 calc GR . . . .
H10B H 0.2668 0.0738 0.5540 0.125 Uiso 1 1 calc GR . . . .
H10C H 0.1412 -0.0254 0.5702 0.125 Uiso 1 1 calc GR . . . .
C11 C 0.42871(17) 0.5733(5) 0.30279(16) 0.0562(5) Uani 1 1 d . . . . .
C12 C 0.49790(18) 0.4790(5) 0.25656(17) 0.0577(5) Uani 1 1 d . . . . .
C13 C 0.58108(16) 0.3727(5) 0.19832(16) 0.0561(5) Uani 1 1 d . . . . .
C14 C 0.6574(3) 0.1705(7) 0.2376(2) 0.0782(8) Uani 1 1 d . . . . .
H14 H 0.6542 0.0980 0.3018 0.094 Uiso 1 1 calc R . . . .
C15 C 0.7392(3) 0.0740(8) 0.1820(3) 0.0940(10) Uani 1 1 d . . . . .
H15 H 0.7917 -0.0607 0.2096 0.113 Uiso 1 1 calc R . . . .
C16 C 0.7428(2) 0.1760(8) 0.0871(2) 0.0853(9) Uani 1 1 d . . . . .
H16 H 0.7967 0.1087 0.0493 0.102 Uiso 1 1 calc R . . . .
C17 C 0.6675(3) 0.3762(9) 0.0476(2) 0.0924(11) Uani 1 1 d . . . . .
H17 H 0.6703 0.4464 -0.0170 0.111 Uiso 1 1 calc R . . . .
C18 C 0.5865(2) 0.4763(8) 0.10335(19) 0.0822(9) Uani 1 1 d . . . . .
H18 H 0.5357 0.6143 0.0762 0.099 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.205(3) . ?
O2 C7 1.205(2) . ?
O3 H3 0.8200 . ?
O3 C8 1.407(3) . ?
N1 C1 1.434(3) . ?
N1 C7 1.400(2) . ?
N1 C9 1.419(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.377(3) . ?
C2 C8 1.504(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.397(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.548(3) . ?
C8 C11 1.473(3) . ?
C9 C10 1.478(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.190(3) . ?
C12 C13 1.440(3) . ?
C13 C14 1.372(4) . ?
C13 C18 1.371(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.363(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.359(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(4) . ?
C18 H18 0.9300 . ?

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
C8 O3 H3 109.5 . . ?
C7 N1 C1 109.26(17) . . ?
C7 N1 C9 126.64(18) . . ?
C9 N1 C1 124.09(17) . . ?
C2 C1 N1 110.00(16) . . ?
C2 C1 C6 120.8(2) . . ?
C6 C1 N1 129.2(2) . . ?
C1 C2 C8 110.00(19) . . ?
C3 C2 C1 121.9(2) . . ?
C3 C2 C8 128.1(2) . . ?
C2 C3 H3A 121.1 . . ?
C2 C3 C4 117.8(3) . . ?
C4 C3 H3A 121.1 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 118.6 . . ?
C4 C5 C6 122.8(2) . . ?
C6 C5 H5 118.6 . . ?
C1 C6 H6 121.6 . . ?
C5 C6 C1 116.8(3) . . ?
C5 C6 H6 121.6 . . ?
O2 C7 N1 127.0(2) . . ?
O2 C7 C8 124.60(18) . . ?
N1 C7 C8 108.40(16) . . ?
O3 C8 C2 111.27(18) . . ?
O3 C8 C7 110.37(16) . . ?
O3 C8 C11 113.04(17) . . ?
C2 C8 C7 101.84(16) . . ?
C11 C8 C2 110.14(16) . . ?
C11 C8 C7 109.62(18) . . ?
O1 C9 N1 118.9(2) . . ?
O1 C9 C10 122.5(3) . . ?
N1 C9 C10 118.6(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 176.3(2) . . ?
C11 C12 C13 178.0(3) . . ?
C14 C13 C12 120.7(2) . . ?
C18 C13 C12 120.2(2) . . ?
C18 C13 C14 119.1(2) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.3(3) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.588

####################################################################### 
# 
# 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_el1345b
_database_code_depnum_ccdc_archive 'CCDC 2097363'
loop_
_audit_author_name
_audit_author_address
'Jose Martin-Alvarez'
;University of Valladolid
Spain
;
_audit_update_record             
;
2021-07-19 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-04-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H20 Cl4 N2 O2'
_chemical_formula_sum            'C30 H20 Cl4 N2 O2'
_chemical_formula_weight         582.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H20 Cl4 N2 O2'
_chemical_oxdiff_usercomment     colorless
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.1758(3)
_cell_length_b                   5.34020(10)
_cell_length_c                   21.8778(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.147(3)
_cell_angle_gamma                90
_cell_volume                     1395.68(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3548
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      74.6930
_cell_measurement_theta_min      3.8310
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.283
_exptl_absorpt_coefficient_mu    4.102
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             596
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -5 0.0348
-1 0 5 0.0168
0 1 0 0.2135
0 -1 0 0.1975
5 0 1 0.0141
-5 0 -1 0.0311

_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.045
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9994 -0.0001 -4.9998 -0.0375 -0.0000 0.3551
-0.9994 0.0001 4.9998 0.0375 0.0000 -0.3551
0.0003 1.0004 -0.0016 0.2771 0.0755 0.0294
-0.0003 -1.0004 0.0016 -0.2771 -0.0755 -0.0294
5.0037 0.0005 1.0021 -0.1759 0.6385 0.0216
-5.0037 -0.0005 -1.0021 0.1759 -0.6385 -0.0216

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9628
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.059
_diffrn_reflns_theta_min         3.700
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00   1.00   1.00   13.82    --  -41.06 122.00-123.00   90
  2  ω    -70.00 -44.00   1.00   13.82    --  -41.06 178.00-120.00   26
  3  ω   -111.00  -8.00   1.00   13.82    --  -41.06 -77.00 150.00  103
  4  ω    -68.00 -39.00   1.00   13.82    --  -41.06 178.00 150.00   29
  5  ω   -100.00 -17.00   1.00   13.82    --  -41.06 -57.00  30.00   83
  6  ω     75.00 134.00   1.00   55.29    --  110.01 -30.00   0.00   59
  7  ω     35.00  60.00   1.00   55.29    --  110.01 -30.00   0.00   25
  8  ω     38.00 134.00   1.00   55.29    --  110.01 -45.00 -90.00   96
  9  ω     65.00 108.00   1.00   55.29    --  110.01-125.00  60.00   43
 10  ω     47.00 116.00   1.00   55.29    --  110.01-125.00 -90.00   69
 11  ω     48.00 115.00   1.00   55.29    --  110.01 -30.00  90.00   67
 12  ω    119.00 165.00   1.00   55.29    --  110.01  30.00-120.00   46
 13  ω     34.00  59.00   1.00   55.29    --  110.01 -94.00 -90.00   25
 14  ω     76.00 110.00   1.00   55.29    --  110.01 -94.00 -90.00   34
 15  ω    102.00 127.00   1.00   55.29    --  110.01 125.00 150.00   25
 16  ω     88.00 114.00   1.00   55.29    --  110.01-122.00 154.00   26
 17  ω    107.00 175.00   1.00   55.29    --  110.01  45.00  30.00   68
 18  ω     79.00 145.00   1.00   55.29    --  110.01 151.00  37.00   66
 19  ω     36.00 141.00   1.00   55.29    --  110.01 -77.00  60.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0352677000
_diffrn_orient_matrix_UB_12      0.2769990000
_diffrn_orient_matrix_UB_13      0.0004528000
_diffrn_orient_matrix_UB_21      0.1226958000
_diffrn_orient_matrix_UB_22      0.0755010000
_diffrn_orient_matrix_UB_23      0.0245245000
_diffrn_orient_matrix_UB_31      0.0178146000
_diffrn_orient_matrix_UB_32      0.0292937000
_diffrn_orient_matrix_UB_33      -0.0674591000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                4885
_reflns_number_total             5556
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5556
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.4413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C10, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C24(H24), C26(H26), C27(H27), C28(H28), C31(H31), C33(H33), C35(H35)
4.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.11707(13) 0.4642(5) 0.08891(10) 0.1170(7) Uani 1 1 d . . . . .
Cl2 Cl 0.53305(14) 0.8517(4) 0.09841(7) 0.1006(6) Uani 1 1 d . . . . .
Cl3 Cl 0.94488(16) 1.0398(4) 0.13684(9) 0.1141(7) Uani 1 1 d . . . . .
Cl4 Cl 0.99056(10) 0.3282(3) 0.31280(7) 0.0807(4) Uani 1 1 d . . . . .
O1 O 0.5856(2) 0.3921(5) 0.21311(14) 0.0586(7) Uani 1 1 d . . . . .
O2 O 0.8767(3) -0.1437(8) 0.49426(18) 0.0860(11) Uani 1 1 d . . . . .
N1 N 0.4219(3) 0.6156(6) 0.19960(15) 0.0463(7) Uani 1 1 d . . . . .
N2 N 0.6495(3) 0.9097(6) 0.26907(17) 0.0518(8) Uani 1 1 d . . . . .
H2 H 0.638365 1.068633 0.269897 0.062 Uiso 1 1 calc R U . . .
C1 C 0.5273(3) 0.5550(7) 0.22934(17) 0.0451(8) Uani 1 1 d . . . . .
C2 C 0.5622(3) 0.7442(7) 0.28403(18) 0.0444(8) Uani 1 1 d . . . . .
C3 C 0.4550(3) 0.8906(7) 0.28106(17) 0.0450(8) Uani 1 1 d . . . . .
C4 C 0.4299(4) 1.0755(9) 0.3196(2) 0.0582(10) Uani 1 1 d . . . . .
H4 H 0.482512 1.129608 0.353675 0.070 Uiso 1 1 calc R U . . .
C5 C 0.3230(4) 1.1799(10) 0.3060(3) 0.0690(13) Uani 1 1 d . . . . .
H5 H 0.304000 1.306405 0.331272 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2454(4) 1.0988(10) 0.2560(2) 0.0678(12) Uani 1 1 d . . . . .
H6 H 0.175047 1.173291 0.247575 0.081 Uiso 1 1 calc R U . . .
C7 C 0.2695(3) 0.9079(9) 0.2175(2) 0.0580(10) Uani 1 1 d . . . . .
H7 H 0.216223 0.849988 0.184237 0.070 Uiso 1 1 calc R U . . .
C8 C 0.3763(3) 0.8076(7) 0.23088(17) 0.0433(7) Uani 1 1 d . . . . .
C9 C 0.3687(4) 0.4909(8) 0.1424(2) 0.0564(10) Uani 1 1 d . . . . .
H9A H 0.308390 0.386570 0.151065 0.068 Uiso 1 1 calc R U . . .
H9B H 0.423099 0.382006 0.128774 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3223(4) 0.6677(9) 0.09007(19) 0.0571(10) Uani 1 1 d . U . . .
C11 C 0.2090(5) 0.6675(12) 0.0624(2) 0.0801(15) Uani 1 1 d . U . . .
C12 C 0.1662(8) 0.826(2) 0.0139(3) 0.128(3) Uani 1 1 d . U . . .
H12 H 0.090448 0.820453 -0.004008 0.153 Uiso 1 1 calc R U . . .
C13 C 0.2352(11) 0.990(2) -0.0077(4) 0.147(4) Uani 1 1 d . U . . .
H13 H 0.206238 1.098577 -0.040146 0.176 Uiso 1 1 calc R U . . .
C14 C 0.3481(9) 0.9979(17) 0.0183(3) 0.127(3) Uani 1 1 d . U . . .
H14 H 0.395156 1.109857 0.003313 0.153 Uiso 1 1 calc R U . . .
C15 C 0.3906(5) 0.8371(11) 0.0668(2) 0.0749(13) Uani 1 1 d . U . . .
C21 C 0.5979(3) 0.6129(7) 0.3434(2) 0.0508(9) Uani 1 1 d . . . . .
C22 C 0.6277(4) 0.5038(8) 0.39136(19) 0.0542(9) Uani 1 1 d . . . . .
C23 C 0.6699(3) 0.3556(8) 0.44559(18) 0.0542(9) Uani 1 1 d . . . . .
C24 C 0.7522(4) 0.1775(9) 0.4417(2) 0.0589(10) Uani 1 1 d . . . . .
H24 H 0.778002 0.157396 0.404694 0.071 Uiso 1 1 calc R U . . .
C25 C 0.7955(4) 0.0304(10) 0.4930(2) 0.0650(11) Uani 1 1 d . . . . .
C26 C 0.7561(5) 0.0596(13) 0.5470(3) 0.0871(17) Uani 1 1 d . . . . .
H26 H 0.785426 -0.037313 0.581659 0.105 Uiso 1 1 calc R U . . .
C27 C 0.6741(6) 0.2295(16) 0.5504(3) 0.104(2) Uani 1 1 d . . . . .
H27 H 0.646825 0.243705 0.587157 0.124 Uiso 1 1 calc R U . . .
C28 C 0.6303(5) 0.3820(12) 0.5002(2) 0.0816(15) Uani 1 1 d . . . . .
H28 H 0.575369 0.499744 0.503365 0.098 Uiso 1 1 calc R U . . .
C29 C 0.9237(6) -0.1719(16) 0.4416(3) 0.106(2) Uani 1 1 d . . . . .
H29A H 0.865718 -0.207626 0.406281 0.159 Uiso 1 1 calc R U . . .
H29B H 0.976437 -0.307414 0.447964 0.159 Uiso 1 1 calc R U . . .
H29C H 0.961283 -0.020016 0.434299 0.159 Uiso 1 1 calc R U . . .
C30 C 0.7492(3) 0.8269(8) 0.25361(18) 0.0480(8) Uani 1 1 d . . . . .
C31 C 0.7917(4) 0.9534(8) 0.2078(2) 0.0556(9) Uani 1 1 d . . . . .
H31 H 0.751932 1.085155 0.186210 0.067 Uiso 1 1 calc R U . . .
C32 C 0.8936(4) 0.8815(10) 0.1948(2) 0.0670(12) Uani 1 1 d . . . . .
C33 C 0.9570(4) 0.6889(10) 0.2253(2) 0.0660(12) Uani 1 1 d . . . . .
H33 H 1.025720 0.644469 0.215908 0.079 Uiso 1 1 calc R U . . .
C34 C 0.9133(3) 0.5661(9) 0.2703(2) 0.0586(10) Uani 1 1 d . . . . .
C35 C 0.8105(3) 0.6263(8) 0.2841(2) 0.0541(9) Uani 1 1 d . . . . .
H35 H 0.782133 0.533778 0.313588 0.065 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
Cl1 C11 1.738(7) . ?
Cl2 C15 1.740(6) . ?
Cl3 C32 1.737(5) . ?
Cl4 C34 1.740(5) . ?
O1 C1 1.218(5) . ?
O2 C25 1.354(6) . ?
O2 C29 1.389(7) . ?
N1 C1 1.362(5) . ?
N1 C8 1.405(5) . ?
N1 C9 1.455(5) . ?
N2 H2 0.8600 . ?
N2 C2 1.467(5) . ?
N2 C30 1.394(5) . ?
C1 C2 1.561(5) . ?
C2 C3 1.512(5) . ?
C2 C21 1.466(6) . ?
C3 C4 1.371(6) . ?
C3 C8 1.383(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.507(6) . ?
C10 C11 1.395(7) . ?
C10 C15 1.391(7) . ?
C11 C12 1.378(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(14) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(14) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(9) . ?
C21 C22 1.194(6) . ?
C22 C23 1.436(6) . ?
C23 C24 1.396(6) . ?
C23 C28 1.380(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(6) . ?
C25 C26 1.369(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.362(9) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(8) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.388(6) . ?
C30 C35 1.399(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.380(6) . ?
C32 C33 1.379(7) . ?
C33 H33 0.9300 . ?
C33 C34 1.372(7) . ?
C34 C35 1.381(6) . ?
C35 H35 0.9300 . ?

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
C25 O2 C29 118.2(4) . . ?
C1 N1 C8 111.4(3) . . ?
C1 N1 C9 121.6(3) . . ?
C8 N1 C9 127.0(3) . . ?
C2 N2 H2 117.8 . . ?
C30 N2 H2 117.8 . . ?
C30 N2 C2 124.4(3) . . ?
O1 C1 N1 125.4(4) . . ?
O1 C1 C2 126.8(3) . . ?
N1 C1 C2 107.7(3) . . ?
N2 C2 C1 108.7(3) . . ?
N2 C2 C3 109.6(3) . . ?
C3 C2 C1 101.4(3) . . ?
C21 C2 N2 112.5(3) . . ?
C21 C2 C1 111.1(3) . . ?
C21 C2 C3 113.0(3) . . ?
C4 C3 C2 129.7(4) . . ?
C4 C3 C8 121.1(4) . . ?
C8 C3 C2 109.2(3) . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.8(4) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.5(4) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.4 . . ?
C8 C7 C6 117.2(4) . . ?
C8 C7 H7 121.4 . . ?
C3 C8 N1 110.0(3) . . ?
C3 C8 C7 121.4(4) . . ?
C7 C8 N1 128.5(4) . . ?
N1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
N1 C9 C10 114.0(4) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C11 C10 C9 121.6(5) . . ?
C15 C10 C9 121.5(4) . . ?
C15 C10 C11 116.9(5) . . ?
C10 C11 Cl1 120.2(5) . . ?
C12 C11 Cl1 117.9(6) . . ?
C12 C11 C10 121.9(7) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(8) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(7) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(8) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 Cl2 120.3(4) . . ?
C14 C15 Cl2 118.2(6) . . ?
C14 C15 C10 121.5(7) . . ?
C22 C21 C2 179.2(5) . . ?
C21 C22 C23 174.0(5) . . ?
C24 C23 C22 118.1(4) . . ?
C28 C23 C22 122.0(4) . . ?
C28 C23 C24 119.8(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.1(4) . . ?
C25 C24 H24 119.9 . . ?
O2 C25 C24 124.6(5) . . ?
O2 C25 C26 115.9(5) . . ?
C26 C25 C24 119.5(5) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.4(5) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.4(5) . . ?
C28 C27 H27 119.3 . . ?
C23 C28 C27 118.7(5) . . ?
C23 C28 H28 120.7 . . ?
C27 C28 H28 120.7 . . ?
O2 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
O2 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N2 C30 C35 122.4(4) . . ?
C31 C30 N2 119.0(4) . . ?
C31 C30 C35 118.6(4) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 C30 119.3(4) . . ?
C32 C31 H31 120.4 . . ?
C31 C32 Cl3 118.7(4) . . ?
C33 C32 Cl3 118.0(4) . . ?
C33 C32 C31 123.3(4) . . ?
C32 C33 H33 121.8 . . ?
C34 C33 C32 116.4(4) . . ?
C34 C33 H33 121.8 . . ?
C33 C34 Cl4 119.2(3) . . ?
C33 C34 C35 122.7(4) . . ?
C35 C34 Cl4 118.1(4) . . ?
C30 C35 H35 120.1 . . ?
C34 C35 C30 119.7(4) . . ?
C34 C35 H35 120.1 . . ?

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
Cl1 C11 C12 C13 179.1(7) . . . . ?
Cl3 C32 C33 C34 -179.3(4) . . . . ?
Cl4 C34 C35 C30 176.0(3) . . . . ?
O1 C1 C2 N2 65.6(5) . . . . ?
O1 C1 C2 C3 -179.0(4) . . . . ?
O1 C1 C2 C21 -58.7(5) . . . . ?
O2 C25 C26 C27 -179.8(6) . . . . ?
N1 C1 C2 N2 -110.0(3) . . . . ?
N1 C1 C2 C3 5.4(4) . . . . ?
N1 C1 C2 C21 125.7(3) . . . . ?
N1 C9 C10 C11 -120.9(5) . . . . ?
N1 C9 C10 C15 59.8(6) . . . . ?
N2 C2 C3 C4 -69.4(5) . . . . ?
N2 C2 C3 C8 111.5(4) . . . . ?
N2 C30 C31 C32 176.3(4) . . . . ?
N2 C30 C35 C34 -174.6(4) . . . . ?
C1 N1 C8 C3 3.7(4) . . . . ?
C1 N1 C8 C7 -175.4(4) . . . . ?
C1 N1 C9 C10 -128.1(4) . . . . ?
C1 C2 C3 C4 175.8(4) . . . . ?
C1 C2 C3 C8 -3.2(4) . . . . ?
C2 N2 C30 C31 141.8(4) . . . . ?
C2 N2 C30 C35 -40.6(6) . . . . ?
C2 C3 C4 C5 -179.9(4) . . . . ?
C2 C3 C8 N1 0.1(4) . . . . ?
C2 C3 C8 C7 179.3(4) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C3 C8 N1 -179.0(4) . . . . ?
C4 C3 C8 C7 0.1(6) . . . . ?
C4 C5 C6 C7 1.0(8) . . . . ?
C5 C6 C7 C8 -1.7(7) . . . . ?
C6 C7 C8 N1 -179.8(4) . . . . ?
C6 C7 C8 C3 1.2(6) . . . . ?
C8 N1 C1 O1 178.6(4) . . . . ?
C8 N1 C1 C2 -5.7(4) . . . . ?
C8 N1 C9 C10 51.2(6) . . . . ?
C8 C3 C4 C5 -0.9(6) . . . . ?
C9 N1 C1 O1 -2.0(6) . . . . ?
C9 N1 C1 C2 173.7(3) . . . . ?
C9 N1 C8 C3 -175.7(4) . . . . ?
C9 N1 C8 C7 5.3(6) . . . . ?
C9 C10 C11 Cl1 1.2(7) . . . . ?
C9 C10 C11 C12 -179.0(6) . . . . ?
C9 C10 C15 Cl2 -0.7(6) . . . . ?
C9 C10 C15 C14 179.3(6) . . . . ?
C10 C11 C12 C13 -0.7(11) . . . . ?
C11 C10 C15 Cl2 179.9(4) . . . . ?
C11 C10 C15 C14 -0.1(8) . . . . ?
C11 C12 C13 C14 0.6(14) . . . . ?
C12 C13 C14 C15 -0.3(14) . . . . ?
C13 C14 C15 Cl2 -180.0(7) . . . . ?
C13 C14 C15 C10 0.0(12) . . . . ?
C15 C10 C11 Cl1 -179.4(4) . . . . ?
C15 C10 C11 C12 0.4(8) . . . . ?
C21 C2 C3 C4 56.9(5) . . . . ?
C21 C2 C3 C8 -122.2(4) . . . . ?
C22 C23 C24 C25 179.9(4) . . . . ?
C22 C23 C28 C27 179.1(6) . . . . ?
C23 C24 C25 O2 -178.7(5) . . . . ?
C23 C24 C25 C26 0.7(8) . . . . ?
C24 C23 C28 C27 0.1(9) . . . . ?
C24 C25 C26 C27 0.7(10) . . . . ?
C25 C26 C27 C28 -1.7(12) . . . . ?
C26 C27 C28 C23 1.3(11) . . . . ?
C28 C23 C24 C25 -1.1(7) . . . . ?
C29 O2 C25 C24 2.7(9) . . . . ?
C29 O2 C25 C26 -176.8(7) . . . . ?
C30 N2 C2 C1 -54.7(5) . . . . ?
C30 N2 C2 C3 -164.6(4) . . . . ?
C30 N2 C2 C21 68.8(5) . . . . ?
C30 C31 C32 Cl3 179.4(4) . . . . ?
C30 C31 C32 C33 -0.3(8) . . . . ?
C31 C30 C35 C34 2.9(6) . . . . ?
C31 C32 C33 C34 0.5(8) . . . . ?
C32 C33 C34 Cl4 -177.7(4) . . . . ?
C32 C33 C34 C35 1.2(8) . . . . ?
C33 C34 C35 C30 -2.9(7) . . . . ?
C35 C30 C31 C32 -1.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.696
