# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_ndj-hz-1-300k
_database_code_depnum_ccdc_archive 'CCDC 1998518'
loop_
_audit_author_name
_audit_author_address
'Youdong Shao'
;Department of Chemistry and Chemical Engineering, Heze University
China
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-07-14 downloaded from the CCDC.
;
_audit_creation_date             2020-03-16
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H21 Cl2 N'
_chemical_formula_sum            'C29 H21 Cl2 N'
_chemical_formula_weight         454.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.3640 0.7020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 '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                   10.8865(3)
_cell_length_b                   8.8581(3)
_cell_length_c                   12.0837(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.528(2)
_cell_angle_gamma                90
_cell_volume                     1155.23(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7594
_cell_measurement_temperature    299.60(10)
_cell_measurement_theta_max      76.5410
_cell_measurement_theta_min      4.1040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             472
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12833
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.873
_diffrn_reflns_theta_min         3.690
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.60(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00 -23.00   0.50    0.05    --  -46.62 125.00  90.00   52
  2  ω    -25.00  39.00   0.50    0.05    --   46.62 -37.00-150.00  128
  3  ω     38.00  81.00   0.50    0.05    --   46.62 -99.00   0.00   86
  4  ω    -27.00  39.00   0.50    0.05    --   46.62 -37.00 -30.00  132
  5  ω     -3.00  28.00   0.50    0.05    --   46.62 -99.00-150.00   62
  6  ω    -27.00  39.00   0.50    0.05    --   46.62 -37.00  90.00  132
  7  ω     36.00  73.00   0.50    0.05    --   46.62 -99.00-150.00   74
  8  ω     -8.00  22.00   0.50    0.05    --   46.62 -19.00  90.00   60
  9  ω     -7.00  34.00   0.50    0.05    --   46.62 -99.00   0.00   82
 10  ω    -83.00 -45.00   0.50    0.15    -- -100.00 125.00   0.00   76
 11  ω    -53.00 -27.00   0.50    0.15    -- -100.00  45.00 150.00   52
 12  ω    -64.00 -27.00   0.50    0.15    -- -100.00  61.00-150.00   74
 13  ω   -112.00 -28.00   0.50    0.15    -- -100.00 125.00  30.00  168
 14  ω   -164.00-138.00   0.50    0.15    -- -100.00 -61.00   0.00   52
 15  ω   -139.00 -84.00   0.50    0.15    -- -100.00-125.00 -30.00  110
 16  ω   -163.00-130.00   0.50    0.15    -- -100.00 -15.00 -60.00   66
 17  ω   -152.00 -87.00   0.50    0.15    -- -100.00 -94.00  90.00  130
 18  ω   -116.00 -82.00   0.50    0.15    -- -100.00 -61.00   0.00   68
 19  ω   -126.00 -89.00   0.50    0.15    -- -100.00 -15.00 -60.00   74
 20  ω   -112.00 -80.00   0.50    0.15    -- -100.00 125.00-150.00   64
 21  ω    -68.00 -27.00   0.50    0.15    -- -100.00  61.00 -30.00   82
 22  ω    -74.00 -27.00   0.50    0.15    -- -100.00  61.00 -60.00   94
 23  ω    -53.00 -28.00   0.50    0.15    -- -100.00  45.00  60.00   50
 24  ω    -63.00 -28.00   0.50    0.15    -- -100.00 125.00-150.00   70
 25  ω    -68.00 -40.00   0.50    0.15    -- -100.00  61.00 120.00   56
 26  ω     77.00 103.00   0.50    0.15    --  107.75-125.00-180.00   52
 27  ω     42.00  67.00   0.50    0.15    --  107.75 -61.00  90.00   50
 28  ω     37.00 102.00   0.50    0.15    --  107.75 -77.00 150.00  130
 29  ω     92.00 159.00   0.50    0.15    --  107.75  30.00  30.00  134
 30  ω     41.00  80.00   0.50    0.15    --  107.75 -94.00 -90.00   78
 31  ω     46.00  95.00   0.50    0.15    --  107.75 -94.00 150.00   98
 32  ω     36.00 105.00   0.50    0.15    --  107.75 -94.00 -30.00  138
 33  ω     59.00 105.00   0.50    0.15    --  107.75 -94.00  90.00   92
 34  ω     78.00 112.00   0.50    0.15    --  107.75-125.00 -30.00   68
 35  ω     82.00 112.00   0.50    0.15    --  107.75-125.00 -90.00   60
 36  ω     40.00  71.00   0.50    0.15    --  107.75-125.00 -90.00   62
 37  ω    134.00 159.00   0.50    0.15    --  107.75  45.00-180.00   50
 38  ω     80.00 112.00   0.50    0.15    --  107.75-125.00  90.00   64
 39  ω     90.00 157.00   0.50    0.15    --  107.75  15.00-180.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0429144000
_diffrn_orient_matrix_UB_12      -0.1574307000
_diffrn_orient_matrix_UB_13      -0.0329997000
_diffrn_orient_matrix_UB_21      0.0150350000
_diffrn_orient_matrix_UB_22      0.0593611000
_diffrn_orient_matrix_UB_23      -0.1172994000
_diffrn_orient_matrix_UB_31      0.1353103000
_diffrn_orient_matrix_UB_32      0.0437495000
_diffrn_orient_matrix_UB_33      0.0412393000
_diffrn_oxdiff_digest_frames     
;
01464fd0855e5e0fc1acddecc12cb7e9fb03304ee11
;
_diffrn_oxdiff_digest_hkl        
;
0154c1c8076431cad9c2ca12a1b246b02f2568
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.802
_reflns_Friedel_fraction_max     0.722
_reflns_number_gt                3745
_reflns_number_total             4168
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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         0.262
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4168
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.079
_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)+(0.1255P)²+0.1362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.1934
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C23(H23A,H23B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C16(H16), C25(H25), C29(H29), C26(H26), C17(H17), C28(H28), C2(H2),
 C15(H15), C18(H18), C8(H8), C14(H14), C13(H13), C9(H9)
;
_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 0.28889(16) 0.5949(5) -0.09536(12) 0.1722(15) Uani 1 1 d . . . . .
Cl2 Cl 0.95760(14) 0.5412(3) 1.05878(11) 0.1108(6) Uani 1 1 d . . . . .
N1 N 0.3795(3) 0.5614(4) 0.3248(3) 0.0624(8) Uani 1 1 d . . . . .
C19 C 0.8074(4) 0.3418(5) 0.3431(4) 0.0703(10) Uani 1 1 d . . . . .
H19 H 0.722583 0.326313 0.340330 0.084 Uiso 1 1 calc R . . . .
C11 C 0.8518(3) 0.4896(5) 0.3384(3) 0.0599(9) Uani 1 1 d . . . . .
C5 C 0.5860(3) 0.5771(5) 0.4237(3) 0.0567(8) Uani 1 1 d . . . . .
C16 C 1.0595(4) 0.3822(7) 0.3545(5) 0.0860(15) Uani 1 1 d . . . . .
H16 H 1.144761 0.394705 0.358625 0.103 Uiso 1 1 calc R . . . .
C4 C 0.4553(3) 0.5586(5) 0.4182(3) 0.0555(7) Uani 1 1 d . . . . .
C12 C 0.9815(3) 0.5115(6) 0.3452(3) 0.0673(10) Uani 1 1 d . . . . .
C24 C 0.6883(3) 0.5785(5) 0.7427(3) 0.0619(9) Uani 1 1 d . . . . .
C6 C 0.6358(3) 0.5983(5) 0.3255(3) 0.0593(9) Uani 1 1 d . . . . .
C20 C 0.6683(3) 0.5738(6) 0.5351(3) 0.0651(10) Uani 1 1 d . . . . .
H20A H 0.731789 0.650577 0.534644 0.078 Uiso 1 1 calc R . . . .
H20B H 0.709537 0.476603 0.543389 0.078 Uiso 1 1 calc R . . . .
C3 C 0.4277(3) 0.5792(5) 0.2272(3) 0.0647(9) Uani 1 1 d . . . . .
C27 C 0.8554(4) 0.5548(6) 0.9354(3) 0.0712(10) Uani 1 1 d . . . . .
C21 C 0.6001(3) 0.5999(6) 0.6351(3) 0.0660(10) Uani 1 1 d . . . . .
H21 H 0.572025 0.705125 0.632611 0.079 Uiso 1 1 calc R . . . .
C10 C 0.7721(3) 0.6187(5) 0.3266(3) 0.0616(9) Uani 1 1 d . . . . .
C7 C 0.5552(3) 0.5980(6) 0.2226(3) 0.0672(10) Uani 1 1 d . . . . .
C23 C 0.3964(3) 0.5419(6) 0.5241(3) 0.0698(11) Uani 1 1 d . . . . .
H23A H 0.333012 0.464506 0.512465 0.084 Uiso 1 1 calc R . . . .
H23B H 0.355929 0.636119 0.538361 0.084 Uiso 1 1 calc R . . . .
C25 C 0.7417(6) 0.4438(7) 0.7769(5) 0.0914(15) Uani 1 1 d . . . . .
H25 H 0.721277 0.357710 0.734389 0.110 Uiso 1 1 calc R . . . .
C29 C 0.7249(5) 0.7027(6) 0.8063(5) 0.0828(13) Uani 1 1 d . . . . .
H29 H 0.692023 0.796619 0.784339 0.099 Uiso 1 1 calc R . . . .
C26 C 0.8254(6) 0.4324(7) 0.8733(5) 0.0970(17) Uani 1 1 d . . . . .
H26 H 0.860649 0.339551 0.894632 0.116 Uiso 1 1 calc R . . . .
C17 C 1.0122(5) 0.2413(8) 0.3574(7) 0.1017(19) Uani 1 1 d . . . . .
H17 H 1.064860 0.158208 0.363270 0.122 Uiso 1 1 calc R . . . .
C28 C 0.8090(6) 0.6925(7) 0.9017(5) 0.0921(16) Uani 1 1 d . . . . .
H28 H 0.833782 0.778711 0.942610 0.111 Uiso 1 1 calc R . . . .
C2 C 0.3455(4) 0.5795(7) 0.1263(4) 0.0825(13) Uani 1 1 d . . . . .
H2 H 0.260740 0.569545 0.127797 0.099 Uiso 1 1 calc R . . . .
C15 C 0.8217(5) 0.7582(6) 0.3190(5) 0.0787(13) Uani 1 1 d . . . . .
H15 H 0.770152 0.842229 0.309324 0.094 Uiso 1 1 calc R . . . .
C22 C 0.4869(4) 0.5008(7) 0.6270(4) 0.0789(13) Uani 1 1 d . . . . .
H22A H 0.446621 0.513125 0.693487 0.095 Uiso 1 1 calc R . . . .
H22B H 0.511213 0.395832 0.622542 0.095 Uiso 1 1 calc R . . . .
C18 C 0.8837(5) 0.2205(7) 0.3517(6) 0.0940(16) Uani 1 1 d . . . . .
H18 H 0.851081 0.123704 0.353806 0.113 Uiso 1 1 calc R . . . .
C8 C 0.5977(4) 0.6121(9) 0.1172(4) 0.0952(18) Uani 1 1 d . . . . .
H8 H 0.681921 0.623335 0.113255 0.114 Uiso 1 1 calc R . . . .
C1 C 0.3901(5) 0.5941(12) 0.0281(4) 0.110(2) Uani 1 1 d . . . . .
C14 C 0.9516(5) 0.7761(7) 0.3257(6) 0.0948(17) Uani 1 1 d . . . . .
H14 H 0.984314 0.872401 0.320350 0.114 Uiso 1 1 calc R . . . .
C13 C 1.0286(4) 0.6575(7) 0.3394(4) 0.0795(13) Uani 1 1 d . . . . .
H13 H 1.113717 0.672618 0.345172 0.095 Uiso 1 1 calc R . . . .
C9 C 0.5170(5) 0.6096(13) 0.0224(4) 0.118(3) Uani 1 1 d . . . . .
H9 H 0.545656 0.617991 -0.046556 0.141 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
Cl1 C1 1.735(5) . ?
Cl2 C27 1.744(4) . ?
N1 C4 1.308(5) . ?
N1 C3 1.362(5) . ?
C19 C11 1.400(7) . ?
C19 C18 1.353(8) . ?
C11 C12 1.417(5) . ?
C11 C10 1.431(6) . ?
C5 C4 1.425(4) . ?
C5 C6 1.380(5) . ?
C5 C20 1.516(5) . ?
C16 C12 1.421(8) . ?
C16 C17 1.352(10) . ?
C4 C23 1.512(5) . ?
C12 C13 1.396(8) . ?
C24 C21 1.524(5) . ?
C24 C25 1.367(7) . ?
C24 C29 1.371(7) . ?
C6 C10 1.493(5) . ?
C6 C7 1.425(5) . ?
C20 C21 1.517(5) . ?
C3 C7 1.406(5) . ?
C3 C2 1.415(5) . ?
C27 C26 1.335(8) . ?
C27 C28 1.362(8) . ?
C21 C22 1.506(6) . ?
C10 C15 1.356(7) . ?
C7 C8 1.416(6) . ?
C23 C22 1.526(6) . ?
C25 C26 1.385(8) . ?
C29 C28 1.378(8) . ?
C17 C18 1.404(8) . ?
C2 C1 1.345(7) . ?
C15 C14 1.415(7) . ?
C8 C9 1.349(7) . ?
C1 C9 1.399(8) . ?
C14 C13 1.340(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
C4 N1 C3 118.5(3) . . ?
C18 C19 C11 122.3(4) . . ?
C19 C11 C12 118.2(4) . . ?
C19 C11 C10 122.9(3) . . ?
C12 C11 C10 118.9(4) . . ?
C4 C5 C20 120.6(3) . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 C20 120.8(3) . . ?
C17 C16 C12 121.4(4) . . ?
N1 C4 C5 123.5(3) . . ?
N1 C4 C23 116.2(3) . . ?
C5 C4 C23 120.2(3) . . ?
C11 C12 C16 118.3(4) . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 C16 122.1(4) . . ?
C25 C24 C21 124.2(4) . . ?
C25 C24 C29 116.8(4) . . ?
C29 C24 C21 118.8(4) . . ?
C5 C6 C10 120.7(3) . . ?
C5 C6 C7 118.9(3) . . ?
C7 C6 C10 120.4(3) . . ?
C5 C20 C21 114.2(3) . . ?
N1 C3 C7 122.9(3) . . ?
N1 C3 C2 118.3(3) . . ?
C7 C3 C2 118.8(4) . . ?
C26 C27 Cl2 120.4(4) . . ?
C26 C27 C28 120.3(4) . . ?
C28 C27 Cl2 119.2(4) . . ?
C20 C21 C24 109.9(3) . . ?
C22 C21 C24 113.7(4) . . ?
C22 C21 C20 110.0(4) . . ?
C11 C10 C6 119.5(4) . . ?
C15 C10 C11 119.6(3) . . ?
C15 C10 C6 120.9(4) . . ?
C3 C7 C6 117.6(3) . . ?
C3 C7 C8 119.1(4) . . ?
C8 C7 C6 123.3(3) . . ?
C4 C23 C22 114.4(3) . . ?
C24 C25 C26 121.6(5) . . ?
C24 C29 C28 121.9(5) . . ?
C27 C26 C25 120.0(5) . . ?
C16 C17 C18 120.0(5) . . ?
C27 C28 C29 119.3(5) . . ?
C1 C2 C3 120.0(4) . . ?
C10 C15 C14 120.1(5) . . ?
C21 C22 C23 110.4(4) . . ?
C19 C18 C17 119.8(6) . . ?
C9 C8 C7 120.6(4) . . ?
C2 C1 Cl1 119.8(4) . . ?
C2 C1 C9 121.7(4) . . ?
C9 C1 Cl1 118.5(4) . . ?
C13 C14 C15 121.6(5) . . ?
C14 C13 C12 120.3(4) . . ?
C8 C9 C1 119.8(4) . . ?

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 C1 C9 C8 178.8(8) . . . . ?
Cl2 C27 C26 C25 178.4(5) . . . . ?
Cl2 C27 C28 C29 -177.8(5) . . . . ?
N1 C4 C23 C22 165.8(4) . . . . ?
N1 C3 C7 C6 -0.1(7) . . . . ?
N1 C3 C7 C8 178.5(5) . . . . ?
N1 C3 C2 C1 -178.8(6) . . . . ?
C19 C11 C12 C16 1.2(6) . . . . ?
C19 C11 C12 C13 179.3(4) . . . . ?
C19 C11 C10 C6 3.5(5) . . . . ?
C19 C11 C10 C15 -177.9(4) . . . . ?
C11 C19 C18 C17 0.8(10) . . . . ?
C11 C12 C13 C14 -1.1(7) . . . . ?
C11 C10 C15 C14 -1.7(7) . . . . ?
C5 C4 C23 C22 -17.0(6) . . . . ?
C5 C6 C10 C11 78.9(5) . . . . ?
C5 C6 C10 C15 -99.7(5) . . . . ?
C5 C6 C7 C3 1.4(6) . . . . ?
C5 C6 C7 C8 -177.1(5) . . . . ?
C5 C20 C21 C24 174.3(4) . . . . ?
C5 C20 C21 C22 48.3(6) . . . . ?
C16 C12 C13 C14 177.0(5) . . . . ?
C16 C17 C18 C19 0.1(12) . . . . ?
C4 N1 C3 C7 -1.4(7) . . . . ?
C4 N1 C3 C2 178.9(4) . . . . ?
C4 C5 C6 C10 179.8(4) . . . . ?
C4 C5 C6 C7 -1.2(6) . . . . ?
C4 C5 C20 C21 -18.4(6) . . . . ?
C4 C23 C22 C21 47.1(6) . . . . ?
C12 C11 C10 C6 -176.7(3) . . . . ?
C12 C11 C10 C15 1.9(5) . . . . ?
C12 C16 C17 C18 -0.2(11) . . . . ?
C24 C21 C22 C23 173.4(4) . . . . ?
C24 C25 C26 C27 0.2(10) . . . . ?
C24 C29 C28 C27 -1.4(9) . . . . ?
C6 C5 C4 N1 -0.4(6) . . . . ?
C6 C5 C4 C23 -177.3(4) . . . . ?
C6 C5 C20 C21 161.4(4) . . . . ?
C6 C10 C15 C14 176.9(5) . . . . ?
C6 C7 C8 C9 179.3(7) . . . . ?
C20 C5 C4 N1 179.5(4) . . . . ?
C20 C5 C4 C23 2.5(6) . . . . ?
C20 C5 C6 C10 -0.1(6) . . . . ?
C20 C5 C6 C7 178.9(4) . . . . ?
C20 C21 C22 C23 -62.9(5) . . . . ?
C3 N1 C4 C5 1.7(6) . . . . ?
C3 N1 C4 C23 178.7(4) . . . . ?
C3 C7 C8 C9 0.8(11) . . . . ?
C3 C2 C1 Cl1 -179.8(6) . . . . ?
C3 C2 C1 C9 -0.1(13) . . . . ?
C21 C24 C25 C26 177.2(5) . . . . ?
C21 C24 C29 C28 -176.9(5) . . . . ?
C10 C11 C12 C16 -178.7(4) . . . . ?
C10 C11 C12 C13 -0.6(6) . . . . ?
C10 C6 C7 C3 -179.6(4) . . . . ?
C10 C6 C7 C8 1.9(8) . . . . ?
C10 C15 C14 C13 0.1(9) . . . . ?
C7 C6 C10 C11 -100.1(5) . . . . ?
C7 C6 C10 C15 81.3(5) . . . . ?
C7 C3 C2 C1 1.5(9) . . . . ?
C7 C8 C9 C1 0.6(14) . . . . ?
C25 C24 C21 C20 -66.0(6) . . . . ?
C25 C24 C21 C22 57.8(6) . . . . ?
C25 C24 C29 C28 -1.6(8) . . . . ?
C29 C24 C21 C20 109.0(5) . . . . ?
C29 C24 C21 C22 -127.3(5) . . . . ?
C29 C24 C25 C26 2.2(9) . . . . ?
C26 C27 C28 C29 3.9(9) . . . . ?
C17 C16 C12 C11 -0.4(8) . . . . ?
C17 C16 C12 C13 -178.5(6) . . . . ?
C28 C27 C26 C25 -3.4(10) . . . . ?
C2 C3 C7 C6 179.6(4) . . . . ?
C2 C3 C7 C8 -1.8(8) . . . . ?
C2 C1 C9 C8 -1.0(16) . . . . ?
C15 C14 C13 C12 1.4(9) . . . . ?
C18 C19 C11 C12 -1.4(7) . . . . ?
C18 C19 C11 C10 178.5(5) . . . . ?

_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 1.827
_oxdiff_exptl_absorpt_empirical_full_min 0.720
####################################################################### 
# 
# 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_ndj-hz-3-300k
_database_code_depnum_ccdc_archive 'CCDC 1998526'
loop_
_audit_author_name
_audit_author_address
'Youdong  Shao'
;Department of Chemistry and Chemical Engineering, Heze University
China
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-07-14 downloaded from the CCDC.
;
_audit_creation_date             2020-03-16
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Cl N'
_chemical_formula_sum            'C23 H18 Cl N'
_chemical_formula_weight         343.83
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.3640 0.7020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 '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                   9.4300(2)
_cell_length_b                   8.4784(2)
_cell_length_c                   11.9996(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.650(2)
_cell_angle_gamma                90
_cell_volume                     897.74(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6127
_cell_measurement_temperature    299.61(10)
_cell_measurement_theta_max      75.9120
_cell_measurement_theta_min      3.9210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             360
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9452
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.831
_diffrn_reflns_theta_min         3.937
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.61(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  27.00   0.50    0.05    --  -46.62  37.00 -30.00  142
  2  ω    -83.00 -34.00   0.50    0.05    --  -46.62 -19.00-180.00   98
  3  ω   -114.00 -87.00   0.50    0.05    --  -46.62 -19.00-180.00   54
  4  ω    -28.00  22.00   0.50    0.05    --  -46.62  19.00 120.00  100
  5  ω   -107.00 -32.00   0.50    0.05    --  -46.62 -37.00 150.00  150
  6  ω    -69.00   0.00   0.50    0.05    --  -46.62  77.00 -30.00  138
  7  ω    -25.00  14.00   0.50    0.05    --   46.62 -19.00  90.00   78
  8  ω    -90.00 -27.00   0.50    0.20    -- -100.00 125.00  90.00  126
  9  ω    -53.00 -28.00   0.50    0.20    -- -100.00  45.00 120.00   50
 10  ω   -107.00 -28.00   0.50    0.20    -- -100.00 125.00  60.00  158
 11  ω   -166.00-116.00   0.50    0.20    -- -100.00 -30.00   0.00  100
 12  ω    -63.00 -30.00   0.50    0.20    -- -100.00  61.00-180.00   66
 13  ω   -168.00-124.00   0.50    0.20    -- -100.00 -94.00 -60.00   88
 14  ω    -92.00 -63.00   0.50    0.20    -- -100.00 125.00 120.00   58
 15  ω   -117.00 -87.00   0.50    0.20    -- -100.00 -94.00 -60.00   60
 16  ω    -92.00 -27.00   0.50    0.20    -- -100.00 125.00 -90.00  130
 17  ω   -164.00 -82.00   0.50    0.20    -- -100.00-125.00-180.00  164
 18  ω   -166.00 -94.00   0.50    0.20    -- -100.00 -45.00  30.00  144
 19  ω   -141.00 -85.00   0.50    0.20    -- -100.00 -30.00-120.00  112
 20  ω     55.00 112.00   0.50    0.20    --  107.75-125.00 -60.00  114
 21  ω     83.00 112.00   0.50    0.20    --  107.75-125.00 -30.00   58
 22  ω     44.00  78.00   0.50    0.20    --  107.75 -94.00-120.00   68
 23  ω    114.00 159.00   0.50    0.20    --  107.75  45.00 -90.00   90
 24  ω    105.00 169.00   0.50    0.20    --  107.75  30.00-150.00  128
 25  ω     40.00  78.00   0.50    0.20    --  107.75 -94.00  30.00   76
 26  ω     38.00 101.00   0.50    0.20    --  107.75 -94.00-180.00  126
 27  ω     40.00  67.00   0.50    0.20    --  107.75 -61.00-180.00   54
 28  ω     40.00  81.00   0.50    0.20    --  107.75 -77.00 -30.00   82
 29  ω     42.00  67.00   0.50    0.20    --  107.75 -61.00  30.00   50
 30  ω     77.00 108.00   0.50    0.20    --  107.75-125.00  30.00   62
 31  ω     80.00 112.00   0.50    0.20    --  107.75-125.00  90.00   64
 32  ω     84.00 112.00   0.50    0.20    --  107.75-125.00-180.00   56
 33  ω     42.00  72.00   0.50    0.20    --  107.75-125.00  30.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0561679000
_diffrn_orient_matrix_UB_12      -0.1702917000
_diffrn_orient_matrix_UB_13      0.0016104000
_diffrn_orient_matrix_UB_21      -0.1653032000
_diffrn_orient_matrix_UB_22      0.0576239000
_diffrn_orient_matrix_UB_23      -0.0533294000
_diffrn_orient_matrix_UB_31      0.0021748000
_diffrn_orient_matrix_UB_32      -0.0264915000
_diffrn_orient_matrix_UB_33      -0.1263855000
_diffrn_oxdiff_digest_frames     
;
01b7b6477beda7cf4f58a39e8eb2f82ef6031046976
;
_diffrn_oxdiff_digest_hkl        
;
019e26fe36e7d7a6c8dc0899209f0bef335867
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.814
_reflns_number_gt                3017
_reflns_number_total             3392
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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         0.247
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.313
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.328
_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)+(0.0617P)²+0.1481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1547
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C21-C20 = C21A-C20 = C23-C22A = C23-C22 = C22-C21 = C22A-C21A
 1.48 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C22A) \\sim Ueq, Uanis(C21A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H23C)=Sof(H23D)=Sof(H20C)=Sof(H20D)=Sof(C22A)=Sof(H22C)=Sof(H22D)=
 Sof(C21A)=Sof(H21C)=Sof(H21D)=1-FVAR(1)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H23A)=Sof(H23B)=Sof(H20A)=Sof(H20B)=Sof(C22)=
 Sof(H22A)=Sof(H22B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C23(H23A,H23B), C23(H23C,H23D), C20(H20A,H20B), C20(H20C,
 H20D), C22(H22A,H22B), C22A(H22C,H22D), C21A(H21C,H21D)
5.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C15(H15), C14(H14), C8(H8), C13(H13), C2(H2), C18(H18),
 C9(H9), C17(H17)
;
_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 0.01917(12) 0.4424(3) 0.11092(8) 0.1023(6) Uani 1 1 d . . . . .
N1 N 0.5411(3) 0.4407(5) 0.4265(2) 0.0544(8) Uani 1 1 d . . . . .
C21 C 0.8601(12) 0.372(2) 0.7682(13) 0.070(4) Uani 0.43(2) 1 d D U P A 1
H21A H 0.870348 0.261620 0.750506 0.084 Uiso 0.43(2) 1 calc R . P A 1
H21B H 0.929414 0.392879 0.848327 0.084 Uiso 0.43(2) 1 calc R . P A 1
C16 C 0.3020(5) 0.6157(6) 0.9535(4) 0.0617(10) Uani 1 1 d . . . . .
H16 H 0.267237 0.600535 1.016294 0.074 Uiso 1 1 calc R . . . .
C11 C 0.3620(4) 0.5116(5) 0.7859(3) 0.0491(8) Uani 1 1 d . . . . .
C12 C 0.3096(4) 0.4850(5) 0.8823(3) 0.0504(9) Uani 1 1 d . . . . .
C7 C 0.3288(4) 0.4139(5) 0.4967(3) 0.0504(8) Uani 1 1 d . . . . .
C19 C 0.4004(5) 0.6668(5) 0.7647(4) 0.0576(10) Uani 1 1 d . . . . .
H19 H 0.431605 0.686369 0.700579 0.069 Uiso 1 1 calc R . . . .
C6 C 0.4324(4) 0.4037(5) 0.6152(3) 0.0503(8) Uani 1 1 d . . . . .
C4 C 0.6345(4) 0.4314(6) 0.5372(3) 0.0522(8) Uani 1 1 d . . . . .
C5 C 0.5861(4) 0.4124(5) 0.6372(3) 0.0521(8) Uani 1 1 d . . . . .
C10 C 0.3739(4) 0.3803(5) 0.7156(3) 0.0500(9) Uani 1 1 d . . . . .
C3 C 0.3896(4) 0.4317(6) 0.4046(3) 0.0522(8) Uani 1 1 d . . . . .
C15 C 0.3334(5) 0.2334(5) 0.7397(4) 0.0578(10) Uani 1 1 d . . . . .
H15 H 0.341565 0.148360 0.693347 0.069 Uiso 1 1 calc R . . . .
C14 C 0.2791(5) 0.2086(6) 0.8342(4) 0.0613(10) Uani 1 1 d . . . . .
H14 H 0.251009 0.107892 0.849024 0.074 Uiso 1 1 calc R . . . .
C8 C 0.1694(4) 0.4073(6) 0.4639(3) 0.0628(11) Uani 1 1 d . . . . .
H8 H 0.127469 0.396122 0.522967 0.075 Uiso 1 1 calc R . . . .
C13 C 0.2679(5) 0.3312(5) 0.9031(3) 0.0568(10) Uani 1 1 d . . . . .
H13 H 0.232199 0.313512 0.965000 0.068 Uiso 1 1 calc R . . . .
C2 C 0.2909(4) 0.4396(7) 0.2853(3) 0.0603(10) Uani 1 1 d . . . . .
H2 H 0.329962 0.450189 0.224510 0.072 Uiso 1 1 calc R . . . .
C23 C 0.8009(4) 0.4398(8) 0.5552(3) 0.0709(12) Uani 1 1 d D . . . .
H23A H 0.831732 0.340234 0.531005 0.085 Uiso 0.43(2) 1 calc R . P A 1
H23B H 0.816102 0.521381 0.503812 0.085 Uiso 0.43(2) 1 calc R . P A 1
H23C H 0.819418 0.374192 0.495502 0.085 Uiso 0.57(2) 1 calc R . P A 2
H23D H 0.825145 0.547583 0.541424 0.085 Uiso 0.57(2) 1 calc R . P A 2
C20 C 0.7014(5) 0.4029(7) 0.7613(3) 0.0697(13) Uani 1 1 d D . . . .
H20A H 0.699801 0.501516 0.801936 0.084 Uiso 0.43(2) 1 calc R . P A 1
H20B H 0.671197 0.319939 0.804000 0.084 Uiso 0.43(2) 1 calc R . P A 1
H20C H 0.710150 0.294132 0.787899 0.084 Uiso 0.57(2) 1 calc R . P A 2
H20D H 0.665679 0.464416 0.814381 0.084 Uiso 0.57(2) 1 calc R . P A 2
C18 C 0.3926(6) 0.7887(6) 0.8366(4) 0.0673(11) Uani 1 1 d . . . . .
H18 H 0.419679 0.889849 0.821731 0.081 Uiso 1 1 calc R . . . .
C9 C 0.0754(4) 0.4168(8) 0.3477(3) 0.0705(12) Uani 1 1 d . . . . .
H9 H -0.029203 0.413440 0.327749 0.085 Uiso 1 1 calc R . . . .
C17 C 0.3441(6) 0.7621(6) 0.9325(4) 0.0687(12) Uani 1 1 d . . . . .
H17 H 0.340692 0.845349 0.982008 0.082 Uiso 1 1 calc R . . . .
C1 C 0.1393(4) 0.4318(7) 0.2590(3) 0.0669(11) Uani 1 1 d . . . . .
C22 C 0.9006(18) 0.474(2) 0.6813(9) 0.070(4) Uani 0.43(2) 1 d D U P A 1
H22A H 0.890138 0.584087 0.699025 0.084 Uiso 0.43(2) 1 calc R . P A 1
H22B H 1.005568 0.455768 0.690051 0.084 Uiso 0.43(2) 1 calc R . P A 1
C22A C 0.9054(13) 0.390(2) 0.6742(7) 0.076(4) Uani 0.57(2) 1 d D U P A 2
H22C H 1.007827 0.423179 0.684851 0.092 Uiso 0.57(2) 1 calc R . P A 2
H22D H 0.904815 0.275868 0.680234 0.092 Uiso 0.57(2) 1 calc R . P A 2
C21A C 0.8568(10) 0.462(2) 0.7704(9) 0.072(3) Uani 0.57(2) 1 d D U P A 2
H21C H 0.854233 0.576376 0.762506 0.086 Uiso 0.57(2) 1 calc R . P A 2
H21D H 0.929988 0.435887 0.848035 0.086 Uiso 0.57(2) 1 calc R . P A 2


_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 C1 1.740(4) . ?
N1 C4 1.311(4) . ?
N1 C3 1.361(4) . ?
C21 C20 1.493(10) . ?
C21 C22 1.506(12) . ?
C16 C12 1.416(6) . ?
C16 C17 1.354(7) . ?
C11 C12 1.428(4) . ?
C11 C19 1.412(6) . ?
C11 C10 1.424(5) . ?
C12 C13 1.409(6) . ?
C7 C6 1.415(5) . ?
C7 C3 1.422(4) . ?
C7 C8 1.415(5) . ?
C19 C18 1.365(6) . ?
C6 C5 1.381(5) . ?
C6 C10 1.505(4) . ?
C4 C5 1.435(4) . ?
C4 C23 1.509(5) . ?
C5 C20 1.505(5) . ?
C10 C15 1.363(6) . ?
C3 C2 1.407(5) . ?
C15 C14 1.415(5) . ?
C14 C13 1.355(6) . ?
C8 C9 1.365(6) . ?
C2 C1 1.353(5) . ?
C23 C22 1.501(10) . ?
C23 C22A 1.483(9) . ?
C20 C21A 1.518(9) . ?
C18 C17 1.399(6) . ?
C9 C1 1.402(5) . ?
C22A C21A 1.515(11) . ?

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
C4 N1 C3 118.5(3) . . ?
C20 C21 C22 110.8(12) . . ?
C17 C16 C12 121.6(4) . . ?
C19 C11 C12 118.5(3) . . ?
C19 C11 C10 122.9(3) . . ?
C10 C11 C12 118.6(3) . . ?
C16 C12 C11 118.1(4) . . ?
C13 C12 C16 122.7(3) . . ?
C13 C12 C11 119.1(3) . . ?
C6 C7 C3 117.6(3) . . ?
C8 C7 C6 124.5(3) . . ?
C8 C7 C3 117.9(3) . . ?
C18 C19 C11 121.2(4) . . ?
C7 C6 C10 119.6(3) . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 C10 120.7(3) . . ?
N1 C4 C5 123.8(3) . . ?
N1 C4 C23 115.8(3) . . ?
C5 C4 C23 120.4(3) . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 C20 122.0(3) . . ?
C4 C5 C20 120.2(3) . . ?
C11 C10 C6 119.9(3) . . ?
C15 C10 C11 120.1(3) . . ?
C15 C10 C6 120.0(3) . . ?
N1 C3 C7 122.6(3) . . ?
N1 C3 C2 117.8(3) . . ?
C2 C3 C7 119.5(3) . . ?
C10 C15 C14 120.9(4) . . ?
C13 C14 C15 120.2(4) . . ?
C9 C8 C7 121.7(3) . . ?
C14 C13 C12 121.0(3) . . ?
C1 C2 C3 120.0(3) . . ?
C22 C23 C4 113.8(7) . . ?
C22A C23 C4 115.4(6) . . ?
C21 C20 C5 115.1(6) . . ?
C5 C20 C21A 113.3(5) . . ?
C19 C18 C17 120.3(4) . . ?
C8 C9 C1 118.9(3) . . ?
C16 C17 C18 120.2(4) . . ?
C2 C1 Cl1 119.3(3) . . ?
C2 C1 C9 121.9(3) . . ?
C9 C1 Cl1 118.7(3) . . ?
C23 C22 C21 111.4(11) . . ?
C23 C22A C21A 110.0(9) . . ?
C22A C21A C20 110.8(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C5 C6 0.0(7) . . . . ?
N1 C4 C5 C20 -179.9(4) . . . . ?
N1 C4 C23 C22 163.8(9) . . . . ?
N1 C4 C23 C22A -165.4(9) . . . . ?
N1 C3 C2 C1 -179.7(5) . . . . ?
C16 C12 C13 C14 -178.9(4) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C11 C19 C18 C17 -0.8(7) . . . . ?
C11 C10 C15 C14 0.0(6) . . . . ?
C12 C16 C17 C18 1.8(7) . . . . ?
C12 C11 C19 C18 2.1(6) . . . . ?
C12 C11 C10 C6 -178.5(3) . . . . ?
C12 C11 C10 C15 1.1(5) . . . . ?
C7 C6 C5 C4 -0.1(6) . . . . ?
C7 C6 C5 C20 179.8(4) . . . . ?
C7 C6 C10 C11 -99.9(4) . . . . ?
C7 C6 C10 C15 80.5(5) . . . . ?
C7 C3 C2 C1 0.6(8) . . . . ?
C7 C8 C9 C1 0.7(8) . . . . ?
C19 C11 C12 C16 -1.4(5) . . . . ?
C19 C11 C12 C13 178.7(4) . . . . ?
C19 C11 C10 C6 1.2(6) . . . . ?
C19 C11 C10 C15 -179.2(4) . . . . ?
C19 C18 C17 C16 -1.1(7) . . . . ?
C6 C7 C3 N1 -0.7(6) . . . . ?
C6 C7 C3 C2 178.9(4) . . . . ?
C6 C7 C8 C9 -179.6(5) . . . . ?
C6 C5 C20 C21 164.6(9) . . . . ?
C6 C5 C20 C21A -162.9(7) . . . . ?
C6 C10 C15 C14 179.6(4) . . . . ?
C4 N1 C3 C7 0.5(7) . . . . ?
C4 N1 C3 C2 -179.1(5) . . . . ?
C4 C5 C20 C21 -15.5(11) . . . . ?
C4 C5 C20 C21A 17.0(9) . . . . ?
C4 C23 C22 C21 47.0(18) . . . . ?
C4 C23 C22A C21A -45.3(16) . . . . ?
C5 C6 C10 C11 81.3(5) . . . . ?
C5 C6 C10 C15 -98.3(5) . . . . ?
C5 C4 C23 C22 -16.8(10) . . . . ?
C5 C4 C23 C22A 14.0(10) . . . . ?
C5 C20 C21A C22A -48.8(14) . . . . ?
C10 C11 C12 C16 178.3(3) . . . . ?
C10 C11 C12 C13 -1.6(5) . . . . ?
C10 C11 C19 C18 -177.6(4) . . . . ?
C10 C6 C5 C4 178.6(4) . . . . ?
C10 C6 C5 C20 -1.5(7) . . . . ?
C10 C15 C14 C13 -0.6(7) . . . . ?
C3 N1 C4 C5 -0.1(7) . . . . ?
C3 N1 C4 C23 179.2(4) . . . . ?
C3 C7 C6 C5 0.5(6) . . . . ?
C3 C7 C6 C10 -178.3(4) . . . . ?
C3 C7 C8 C9 0.3(7) . . . . ?
C3 C2 C1 Cl1 179.8(4) . . . . ?
C3 C2 C1 C9 0.4(9) . . . . ?
C15 C14 C13 C12 0.1(6) . . . . ?
C8 C7 C6 C5 -179.6(4) . . . . ?
C8 C7 C6 C10 1.6(6) . . . . ?
C8 C7 C3 N1 179.4(4) . . . . ?
C8 C7 C3 C2 -1.0(7) . . . . ?
C8 C9 C1 Cl1 179.5(5) . . . . ?
C8 C9 C1 C2 -1.1(9) . . . . ?
C23 C4 C5 C6 -179.3(4) . . . . ?
C23 C4 C5 C20 0.8(7) . . . . ?
C23 C22A C21A C20 63.5(18) . . . . ?
C20 C21 C22 C23 -62(2) . . . . ?
C17 C16 C12 C11 -0.6(6) . . . . ?
C17 C16 C12 C13 179.3(4) . . . . ?
C22 C21 C20 C5 45.3(17) . . . . ?

_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 1.637
_oxdiff_exptl_absorpt_empirical_full_min 0.249
####################################################################### 
# 
# 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_ndj-hz-2-300k
_database_code_depnum_ccdc_archive 'CCDC 1998519'
loop_
_audit_author_name
_audit_author_address
'Youdong  Shao'
;Department of Chemistry and Chemical Engineering, Heze University
China
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-07-14 downloaded from the CCDC.
;
_audit_creation_date             2020-03-16
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Cl N O'
_chemical_formula_sum            'C22 H16 Cl N O'
_chemical_formula_weight         345.81
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.3640 0.7020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.35760(10)
_cell_length_b                   18.24240(10)
_cell_length_c                   20.28210(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3462.26(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    30698
_cell_measurement_temperature    299.69(10)
_cell_measurement_theta_max      77.0750
_cell_measurement_theta_min      4.3530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.011
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            46005
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.281
_diffrn_reflns_theta_min         3.258
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.69(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00 -24.00   0.50    0.05    --  -46.62 125.00 150.00  122
  2  ω    -25.00   1.00   0.50    0.05    --   46.62 -19.00-180.00   52
  3  ω     59.00  89.00   0.50    0.05    --   46.62-125.00  30.00   60
  4  ω    -24.00  63.00   0.50    0.05    --   46.62 -57.00  30.00  174
  5  ω     17.00  56.00   0.50    0.05    --   46.62-125.00  30.00   78
  6  ω     12.00  38.00   0.50    0.05    --   46.62 -37.00  30.00   52
  7  ω      1.00  39.00   0.50    0.05    --   46.62 -37.00 120.00   76
  8  ω     27.00 120.00   0.50    0.05    --   46.62  77.00 150.00  186
  9  ω    -53.00 -27.00   0.50    0.15    -- -100.00  45.00-120.00   52
 10  ω   -109.00 -84.00   0.50    0.15    -- -100.00 -30.00   0.00   50
 11  ω   -108.00 -71.00   0.50    0.15    -- -100.00 112.00  77.02   74
 12  ω    -59.00 -30.00   0.50    0.15    -- -100.00  61.00 150.00   58
 13  ω   -153.00 -85.00   0.50    0.15    -- -100.00 -30.00  30.00  136
 14  ω   -166.00-115.00   0.50    0.15    -- -100.00 -30.00   0.00  102
 15  ω    -65.00 -33.00   0.50    0.15    -- -100.00 112.00  77.02   64
 16  ω   -108.00 -42.00   0.50    0.15    -- -100.00  77.00  30.00  132
 17  ω   -112.00 -65.00   0.50    0.15    -- -100.00 125.00 150.00   94
 18  ω    -71.00 -46.00   0.50    0.15    -- -100.00  61.00 -60.00   50
 19  ω   -164.00 -92.00   0.50    0.15    -- -100.00 -45.00  90.00  144
 20  ω    -60.00 -35.00   0.50    0.15    -- -100.00 125.00 150.00   50
 21  ω   -138.00-112.00   0.50    0.15    -- -100.00 -77.00-150.00   52
 22  ω   -102.00 -77.00   0.50    0.15    -- -100.00 -77.00-150.00   50
 23  ω   -132.00 -84.00   0.50    0.15    -- -100.00 -30.00 -60.00   96
 24  ω    -69.00 -37.00   0.50    0.15    -- -100.00  77.00-180.00   64
 25  ω    -66.00 -30.00   0.50    0.15    -- -100.00 115.00-162.20   72
 26  ω   -167.00-135.00   0.50    0.15    -- -100.00 -30.00 -90.00   64
 27  ω   -167.00-136.00   0.50    0.15    -- -100.00 -30.00 -60.00   62
 28  ω   -109.00 -79.00   0.50    0.15    -- -100.00 115.00-162.20   60
 29  ω    -56.00 -31.00   0.50    0.15    -- -100.00  61.00-180.00   50
 30  ω   -165.00 -93.00   0.50    0.15    -- -100.00-125.00  30.00  144
 31  ω   -106.00 -74.00   0.50    0.15    -- -100.00  77.00-180.00   64
 32  ω    -73.00 -47.00   0.50    0.15    -- -100.00  61.00 -30.00   52
 33  ω   -116.00 -84.00   0.50    0.15    -- -100.00 -30.00 -90.00   64
 34  ω     64.00 112.00   0.50    0.15    --  107.75-125.00 -90.00   96
 35  ω     73.00 105.00   0.50    0.15    --  107.75 -94.00 -30.00   64
 36  ω     40.00  69.00   0.50    0.15    --  107.75 -94.00 -30.00   58
 37  ω     35.00  68.00   0.50    0.15    --  107.75 -61.00  30.00   66
 38  ω     73.00  98.00   0.50    0.15    --  107.75 -94.00 120.00   50
 39  ω     86.00 112.00   0.50    0.15    --  107.75-125.00 -30.00   52
 40  ω    142.00 168.00   0.50    0.15    --  107.75  45.00   0.00   52
 41  ω     49.00 106.00   0.50    0.15    --  107.75 -94.00  30.00  114
 42  ω     93.00 132.00   0.50    0.15    --  107.75  45.00   0.00   78
 43  ω     40.00 112.00   0.50    0.15    --  107.75-125.00 -60.00  144
 44  ω     71.00 106.00   0.50    0.15    --  107.75 -94.00 -90.00   70
 45  ω    113.00 168.00   0.50    0.15    --  107.75  45.00 -90.00  110
 46  ω     73.00 112.00   0.50    0.15    --  107.75-125.00  60.00   78
 47  ω     46.00  80.00   0.50    0.15    --  107.75 -94.00  90.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0144378000
_diffrn_orient_matrix_UB_12      -0.0400442000
_diffrn_orient_matrix_UB_13      -0.0665191000
_diffrn_orient_matrix_UB_21      0.1453394000
_diffrn_orient_matrix_UB_22      -0.0313384000
_diffrn_orient_matrix_UB_23      0.0219729000
_diffrn_orient_matrix_UB_31      -0.0760155000
_diffrn_orient_matrix_UB_32      -0.0674177000
_diffrn_orient_matrix_UB_33      0.0293461000
_diffrn_oxdiff_digest_frames     
;
01fe9b598f065bf496e040597e2a048b87038001de6
;
_diffrn_oxdiff_digest_hkl        
;
01b3377d977ed2ccd4dae612ea4cb799f50676
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                6719
_reflns_number_total             7109
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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         0.503
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 2794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.051
_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)+(0.0723P)²+0.3654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1162
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B), C28(H28A,H28B), C30(H30A,H30B),
 C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C22(H22), C12(H12), C18(H18), C19(H19), C16(H16), C17(H17),
 C21(H21), C20(H20), C24(H24), C44(H44), C34(H34), C38(H38), C33(H33), C40(H40),
  C41(H41), C43(H43), C42(H42), C39(H39)
;
_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 0.69941(9) 0.38651(4) 0.75946(4) 0.0735(2) Uani 1 1 d . . . . .
O1 O 0.0047(3) 0.08292(15) 0.63030(14) 0.0898(7) Uani 1 1 d . . . . .
N1 N 0.3456(2) 0.18174(11) 0.72124(10) 0.0506(4) Uani 1 1 d . . . . .
C3 C 0.3960(3) 0.24754(12) 0.69947(11) 0.0470(5) Uani 1 1 d . . . . .
C10 C 0.3445(3) 0.28173(13) 0.64139(11) 0.0485(5) Uani 1 1 d . . . . .
C4 C 0.2460(3) 0.14918(13) 0.68633(12) 0.0506(5) Uani 1 1 d . . . . .
C5 C 0.1865(3) 0.17881(14) 0.62739(12) 0.0527(5) Uani 1 1 d . . . . .
C9 C 0.2358(3) 0.24534(14) 0.60508(11) 0.0503(5) Uani 1 1 d . . . . .
C2 C 0.5054(3) 0.28111(13) 0.73631(11) 0.0514(5) Uani 1 1 d . . . . .
H2 H 0.538626 0.259441 0.774878 0.062 Uiso 1 1 calc R . . . .
C11 C 0.4074(3) 0.34906(15) 0.62166(13) 0.0578(6) Uani 1 1 d . . . . .
H11 H 0.374762 0.372229 0.583684 0.069 Uiso 1 1 calc R . . . .
C13 C 0.1808(3) 0.27911(15) 0.54242(12) 0.0551(6) Uani 1 1 d . . . . .
C14 C 0.0826(3) 0.33835(15) 0.54442(13) 0.0574(6) Uani 1 1 d . . . . .
C1 C 0.5620(3) 0.34554(14) 0.71499(13) 0.0548(5) Uani 1 1 d . . . . .
C22 C 0.0249(4) 0.36651(17) 0.60351(16) 0.0678(7) Uani 1 1 d . . . . .
H22 H 0.052077 0.346389 0.643737 0.081 Uiso 1 1 calc R . . . .
C6 C 0.0736(3) 0.13619(18) 0.59041(15) 0.0673(7) Uani 1 1 d . . . . .
H6A H 0.002632 0.170086 0.573530 0.081 Uiso 1 1 calc R . . . .
H6B H 0.117635 0.111919 0.553011 0.081 Uiso 1 1 calc R . . . .
C15 C 0.0384(3) 0.37000(17) 0.48326(15) 0.0691(8) Uani 1 1 d . . . . .
C8 C 0.1915(3) 0.07693(14) 0.71196(16) 0.0644(7) Uani 1 1 d . . . . .
H8A H 0.272096 0.046294 0.724022 0.077 Uiso 1 1 calc R . . . .
H8B H 0.135214 0.085466 0.751380 0.077 Uiso 1 1 calc R . . . .
C12 C 0.5140(3) 0.38022(15) 0.65715(14) 0.0607(6) Uani 1 1 d . . . . .
H12 H 0.555087 0.424064 0.643403 0.073 Uiso 1 1 calc R . . . .
C18 C 0.2297(4) 0.2521(2) 0.48320(13) 0.0699(7) Uani 1 1 d . . . . .
H18 H 0.292408 0.212509 0.482845 0.084 Uiso 1 1 calc R . . . .
C19 C -0.0609(4) 0.4280(2) 0.4844(2) 0.0887(11) Uani 1 1 d . . . . .
H19 H -0.089711 0.449179 0.444890 0.106 Uiso 1 1 calc R . . . .
C16 C 0.0932(4) 0.3412(2) 0.42363(15) 0.0806(10) Uani 1 1 d . . . . .
H16 H 0.065486 0.362064 0.383805 0.097 Uiso 1 1 calc R . . . .
C17 C 0.1859(4) 0.2835(2) 0.42329(15) 0.0818(10) Uani 1 1 d . . . . .
H17 H 0.219916 0.265032 0.383545 0.098 Uiso 1 1 calc R . . . .
C21 C -0.0707(5) 0.4233(2) 0.6020(2) 0.0896(10) Uani 1 1 d . . . . .
H21 H -0.106690 0.441875 0.641333 0.108 Uiso 1 1 calc R . . . .
C7 C 0.1018(4) 0.03737(18) 0.6622(2) 0.0823(9) Uani 1 1 d . . . . .
H7A H 0.163937 0.015053 0.629642 0.099 Uiso 1 1 calc R . . . .
H7B H 0.049892 -0.001655 0.684195 0.099 Uiso 1 1 calc R . . . .
C20 C -0.1154(5) 0.4538(2) 0.5418(3) 0.1023(14) Uani 1 1 d . . . . .
H20 H -0.182129 0.491537 0.541308 0.123 Uiso 1 1 calc R . . . .
Cl2 Cl 0.41427(10) 0.51826(4) 0.79209(4) 0.0784(2) Uani 1 1 d . . . . .
O2 O -0.0885(3) 0.10357(15) 0.82609(14) 0.0917(7) Uani 1 1 d . . . . .
N2 N 0.0659(2) 0.30678(14) 0.77608(10) 0.0576(5) Uani 1 1 d . . . . .
C36 C 0.3401(3) 0.15260(13) 0.95021(12) 0.0522(5) Uani 1 1 d . . . . .
C25 C 0.1733(3) 0.33820(14) 0.81146(12) 0.0514(5) Uani 1 1 d . . . . .
C35 C 0.2258(3) 0.20402(14) 0.95325(12) 0.0554(6) Uani 1 1 d . . . . .
C37 C 0.3952(3) 0.12319(14) 1.01017(12) 0.0553(5) Uani 1 1 d . . . . .
C24 C 0.2301(3) 0.40524(15) 0.78801(13) 0.0571(6) Uani 1 1 d . . . . .
H24 H 0.193959 0.426858 0.749974 0.068 Uiso 1 1 calc R . . . .
C32 C 0.2292(3) 0.30601(15) 0.86971(12) 0.0520(5) Uani 1 1 d . . . . .
C23 C 0.3378(3) 0.43731(15) 0.82187(13) 0.0597(6) Uani 1 1 d . . . . .
C44 C 0.4032(3) 0.13007(16) 0.89009(13) 0.0623(6) Uani 1 1 d . . . . .
H44 H 0.367806 0.147857 0.850353 0.075 Uiso 1 1 calc R . . . .
C26 C 0.0127(3) 0.24443(16) 0.79748(13) 0.0572(6) Uani 1 1 d . . . . .
C31 C 0.1698(3) 0.23875(15) 0.89154(12) 0.0542(5) Uani 1 1 d . . . . .
C34 C 0.3954(4) 0.40738(16) 0.87957(15) 0.0663(7) Uani 1 1 d . . . . .
H34 H 0.469260 0.431016 0.901665 0.080 Uiso 1 1 calc R . . . .
C38 C 0.3337(4) 0.14558(17) 1.07089(13) 0.0653(7) Uani 1 1 d . . . . .
H38 H 0.369483 0.127204 1.110338 0.078 Uiso 1 1 calc R . . . .
C33 C 0.3414(3) 0.34307(17) 0.90282(14) 0.0634(7) Uani 1 1 d . . . . .
H33 H 0.378930 0.323016 0.941257 0.076 Uiso 1 1 calc R . . . .
C40 C 0.1697(4) 0.22363(18) 1.01276(14) 0.0687(7) Uani 1 1 d . . . . .
H40 H 0.095258 0.257336 1.014382 0.082 Uiso 1 1 calc R . . . .
C27 C 0.0615(3) 0.20836(16) 0.85560(13) 0.0587(6) Uani 1 1 d . . . . .
C41 C 0.5106(4) 0.07378(17) 1.00795(16) 0.0702(7) Uani 1 1 d . . . . .
H41 H 0.547234 0.054664 1.046948 0.084 Uiso 1 1 calc R . . . .
C43 C 0.5159(4) 0.08240(19) 0.89003(17) 0.0771(8) Uani 1 1 d . . . . .
H43 H 0.557563 0.068886 0.850221 0.093 Uiso 1 1 calc R . . . .
C42 C 0.5693(4) 0.0537(2) 0.94892(19) 0.0825(9) Uani 1 1 d . . . . .
H42 H 0.645060 0.020703 0.947983 0.099 Uiso 1 1 calc R . . . .
C39 C 0.2230(4) 0.19354(19) 1.07178(14) 0.0732(8) Uani 1 1 d . . . . .
H39 H 0.181916 0.206728 1.111800 0.088 Uiso 1 1 calc R . . . .
C28 C -0.0120(4) 0.13810(19) 0.87694(18) 0.0795(9) Uani 1 1 d . . . . .
H28A H 0.059435 0.104356 0.893633 0.095 Uiso 1 1 calc R . . . .
H28B H -0.077217 0.149163 0.912767 0.095 Uiso 1 1 calc R . . . .
C30 C -0.1042(3) 0.2104(2) 0.75731(17) 0.0738(8) Uani 1 1 d . . . . .
H30A H -0.169879 0.248321 0.743060 0.089 Uiso 1 1 calc R . . . .
H30B H -0.063118 0.188053 0.718256 0.089 Uiso 1 1 calc R . . . .
C29 C -0.1844(4) 0.1538(2) 0.7950(2) 0.0939(11) Uani 1 1 d . . . . .
H29A H -0.242935 0.177454 0.828270 0.113 Uiso 1 1 calc R . . . .
H29B H -0.247220 0.127253 0.765418 0.113 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
Cl1 C1 1.740(3) . ?
O1 C6 1.420(4) . ?
O1 C7 1.391(5) . ?
N1 C3 1.363(3) . ?
N1 C4 1.312(3) . ?
C3 C10 1.417(3) . ?
C3 C2 1.407(4) . ?
C10 C9 1.421(3) . ?
C10 C11 1.420(4) . ?
C4 C5 1.425(4) . ?
C4 C8 1.506(4) . ?
C5 C9 1.375(4) . ?
C5 C6 1.511(4) . ?
C9 C13 1.503(3) . ?
C2 C1 1.360(4) . ?
C11 C12 1.356(4) . ?
C13 C14 1.420(4) . ?
C13 C18 1.377(4) . ?
C14 C22 1.411(4) . ?
C14 C15 1.429(4) . ?
C1 C12 1.406(4) . ?
C22 C21 1.369(5) . ?
C15 C19 1.409(5) . ?
C15 C16 1.415(5) . ?
C8 C7 1.498(5) . ?
C18 C17 1.405(5) . ?
C19 C20 1.353(7) . ?
C16 C17 1.363(6) . ?
C21 C20 1.406(6) . ?
Cl2 C23 1.748(3) . ?
O2 C28 1.404(4) . ?
O2 C29 1.429(5) . ?
N2 C25 1.361(3) . ?
N2 C26 1.315(4) . ?
C36 C35 1.424(4) . ?
C36 C37 1.426(4) . ?
C36 C44 1.416(4) . ?
C25 C24 1.416(4) . ?
C25 C32 1.419(3) . ?
C35 C31 1.497(3) . ?
C35 C40 1.364(4) . ?
C37 C38 1.419(4) . ?
C37 C41 1.407(4) . ?
C24 C23 1.353(4) . ?
C32 C31 1.418(4) . ?
C32 C33 1.418(4) . ?
C23 C34 1.399(4) . ?
C44 C43 1.366(5) . ?
C26 C27 1.425(4) . ?
C26 C30 1.499(4) . ?
C31 C27 1.366(4) . ?
C34 C33 1.362(4) . ?
C38 C39 1.356(5) . ?
C40 C39 1.408(4) . ?
C27 C28 1.518(4) . ?
C41 C42 1.367(5) . ?
C43 C42 1.397(5) . ?
C30 C29 1.488(6) . ?

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
C7 O1 C6 112.2(3) . . ?
C4 N1 C3 118.0(2) . . ?
N1 C3 C10 122.6(2) . . ?
N1 C3 C2 117.6(2) . . ?
C2 C3 C10 119.8(2) . . ?
C3 C10 C9 118.0(2) . . ?
C3 C10 C11 118.3(2) . . ?
C11 C10 C9 123.7(2) . . ?
N1 C4 C5 123.9(2) . . ?
N1 C4 C8 116.8(2) . . ?
C5 C4 C8 119.3(2) . . ?
C4 C5 C6 119.6(2) . . ?
C9 C5 C4 118.7(2) . . ?
C9 C5 C6 121.7(2) . . ?
C10 C9 C13 119.5(2) . . ?
C5 C9 C10 118.8(2) . . ?
C5 C9 C13 121.7(2) . . ?
C1 C2 C3 119.4(2) . . ?
C12 C11 C10 121.2(2) . . ?
C14 C13 C9 120.6(2) . . ?
C18 C13 C9 118.5(3) . . ?
C18 C13 C14 120.9(2) . . ?
C13 C14 C15 118.0(3) . . ?
C22 C14 C13 123.3(2) . . ?
C22 C14 C15 118.7(3) . . ?
C2 C1 Cl1 119.6(2) . . ?
C2 C1 C12 122.0(2) . . ?
C12 C1 Cl1 118.4(2) . . ?
C21 C22 C14 120.4(3) . . ?
O1 C6 C5 112.8(2) . . ?
C19 C15 C14 118.6(3) . . ?
C19 C15 C16 122.2(3) . . ?
C16 C15 C14 119.1(3) . . ?
C7 C8 C4 112.3(3) . . ?
C11 C12 C1 119.3(2) . . ?
C13 C18 C17 120.8(3) . . ?
C20 C19 C15 121.6(3) . . ?
C17 C16 C15 121.4(3) . . ?
C16 C17 C18 119.8(3) . . ?
C22 C21 C20 120.9(4) . . ?
O1 C7 C8 113.1(3) . . ?
C19 C20 C21 119.8(4) . . ?
C28 O2 C29 110.9(3) . . ?
C26 N2 C25 118.0(2) . . ?
C35 C36 C37 118.9(2) . . ?
C44 C36 C35 122.8(2) . . ?
C44 C36 C37 118.3(2) . . ?
N2 C25 C24 117.6(2) . . ?
N2 C25 C32 122.5(2) . . ?
C24 C25 C32 119.9(2) . . ?
C36 C35 C31 120.3(2) . . ?
C40 C35 C36 120.0(2) . . ?
C40 C35 C31 119.6(3) . . ?
C38 C37 C36 119.0(2) . . ?
C41 C37 C36 119.4(2) . . ?
C41 C37 C38 121.6(3) . . ?
C23 C24 C25 118.9(2) . . ?
C31 C32 C25 118.3(2) . . ?
C33 C32 C25 118.0(2) . . ?
C33 C32 C31 123.7(2) . . ?
C24 C23 Cl2 119.7(2) . . ?
C24 C23 C34 122.9(3) . . ?
C34 C23 Cl2 117.5(2) . . ?
C43 C44 C36 120.5(3) . . ?
N2 C26 C27 123.5(3) . . ?
N2 C26 C30 117.1(3) . . ?
C27 C26 C30 119.5(3) . . ?
C32 C31 C35 119.4(2) . . ?
C27 C31 C35 122.3(2) . . ?
C27 C31 C32 118.4(2) . . ?
C33 C34 C23 118.9(3) . . ?
C39 C38 C37 120.5(3) . . ?
C34 C33 C32 121.4(3) . . ?
C35 C40 C39 120.9(3) . . ?
C26 C27 C28 118.7(3) . . ?
C31 C27 C26 119.4(2) . . ?
C31 C27 C28 121.8(3) . . ?
C42 C41 C37 120.5(3) . . ?
C44 C43 C42 120.9(3) . . ?
C41 C42 C43 120.3(3) . . ?
C38 C39 C40 120.7(3) . . ?
O2 C28 C27 113.6(3) . . ?
C29 C30 C26 112.1(3) . . ?
O2 C29 C30 110.8(3) . . ?

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 C1 C12 C11 179.8(2) . . . . ?
N1 C3 C10 C9 0.2(3) . . . . ?
N1 C3 C10 C11 -177.9(2) . . . . ?
N1 C3 C2 C1 177.8(2) . . . . ?
N1 C4 C5 C9 0.2(4) . . . . ?
N1 C4 C5 C6 179.1(2) . . . . ?
N1 C4 C8 C7 -168.2(3) . . . . ?
C3 N1 C4 C5 -0.6(4) . . . . ?
C3 N1 C4 C8 -179.4(2) . . . . ?
C3 C10 C9 C5 -0.5(3) . . . . ?
C3 C10 C9 C13 -178.6(2) . . . . ?
C3 C10 C11 C12 0.0(4) . . . . ?
C3 C2 C1 Cl1 -178.84(19) . . . . ?
C3 C2 C1 C12 0.4(4) . . . . ?
C10 C3 C2 C1 -1.1(4) . . . . ?
C10 C9 C13 C14 -77.9(3) . . . . ?
C10 C9 C13 C18 101.1(3) . . . . ?
C10 C11 C12 C1 -0.8(4) . . . . ?
C4 N1 C3 C10 0.4(3) . . . . ?
C4 N1 C3 C2 -178.4(2) . . . . ?
C4 C5 C9 C10 0.4(4) . . . . ?
C4 C5 C9 C13 178.4(2) . . . . ?
C4 C5 C6 O1 20.3(4) . . . . ?
C4 C8 C7 O1 -44.2(4) . . . . ?
C5 C4 C8 C7 12.9(4) . . . . ?
C5 C9 C13 C14 104.1(3) . . . . ?
C5 C9 C13 C18 -76.9(3) . . . . ?
C9 C10 C11 C12 -177.9(3) . . . . ?
C9 C5 C6 O1 -160.8(3) . . . . ?
C9 C13 C14 C22 -3.4(4) . . . . ?
C9 C13 C14 C15 177.6(2) . . . . ?
C9 C13 C18 C17 -177.6(3) . . . . ?
C2 C3 C10 C9 178.9(2) . . . . ?
C2 C3 C10 C11 0.9(4) . . . . ?
C2 C1 C12 C11 0.6(4) . . . . ?
C11 C10 C9 C5 177.4(2) . . . . ?
C11 C10 C9 C13 -0.7(4) . . . . ?
C13 C14 C22 C21 -179.3(3) . . . . ?
C13 C14 C15 C19 179.0(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C13 C18 C17 C16 -0.4(5) . . . . ?
C14 C13 C18 C17 1.4(5) . . . . ?
C14 C22 C21 C20 1.1(6) . . . . ?
C14 C15 C19 C20 -0.4(5) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C22 C14 C15 C19 0.0(4) . . . . ?
C22 C14 C15 C16 -178.7(3) . . . . ?
C22 C21 C20 C19 -1.5(7) . . . . ?
C6 O1 C7 C8 65.8(4) . . . . ?
C6 C5 C9 C10 -178.5(2) . . . . ?
C6 C5 C9 C13 -0.5(4) . . . . ?
C15 C14 C22 C21 -0.3(5) . . . . ?
C15 C19 C20 C21 1.2(6) . . . . ?
C15 C16 C17 C18 -0.7(5) . . . . ?
C8 C4 C5 C9 179.0(2) . . . . ?
C8 C4 C5 C6 -2.1(4) . . . . ?
C18 C13 C14 C22 177.6(3) . . . . ?
C18 C13 C14 C15 -1.3(4) . . . . ?
C19 C15 C16 C17 -177.9(3) . . . . ?
C16 C15 C19 C20 178.2(4) . . . . ?
C7 O1 C6 C5 -51.9(4) . . . . ?
Cl2 C23 C34 C33 -177.8(3) . . . . ?
N2 C25 C24 C23 -179.4(2) . . . . ?
N2 C25 C32 C31 -0.3(4) . . . . ?
N2 C25 C32 C33 179.8(2) . . . . ?
N2 C26 C27 C31 -0.6(4) . . . . ?
N2 C26 C27 C28 177.6(3) . . . . ?
N2 C26 C30 C29 -163.1(3) . . . . ?
C36 C35 C31 C32 -91.1(3) . . . . ?
C36 C35 C31 C27 89.8(3) . . . . ?
C36 C35 C40 C39 -0.2(5) . . . . ?
C36 C37 C38 C39 0.8(4) . . . . ?
C36 C37 C41 C42 -0.4(5) . . . . ?
C36 C44 C43 C42 1.4(5) . . . . ?
C25 N2 C26 C27 0.1(4) . . . . ?
C25 N2 C26 C30 -179.3(2) . . . . ?
C25 C24 C23 Cl2 177.5(2) . . . . ?
C25 C24 C23 C34 -0.4(4) . . . . ?
C25 C32 C31 C35 -179.3(2) . . . . ?
C25 C32 C31 C27 -0.2(4) . . . . ?
C25 C32 C33 C34 -0.5(4) . . . . ?
C35 C36 C37 C38 0.5(4) . . . . ?
C35 C36 C37 C41 -178.4(2) . . . . ?
C35 C36 C44 C43 177.8(3) . . . . ?
C35 C31 C27 C26 179.7(2) . . . . ?
C35 C31 C27 C28 1.6(4) . . . . ?
C35 C40 C39 C38 1.5(5) . . . . ?
C37 C36 C35 C31 177.1(2) . . . . ?
C37 C36 C35 C40 -0.8(4) . . . . ?
C37 C36 C44 C43 -1.2(4) . . . . ?
C37 C38 C39 C40 -1.8(5) . . . . ?
C37 C41 C42 C43 0.5(5) . . . . ?
C24 C25 C32 C31 -179.8(2) . . . . ?
C24 C25 C32 C33 0.2(4) . . . . ?
C24 C23 C34 C33 0.2(5) . . . . ?
C32 C25 C24 C23 0.2(4) . . . . ?
C32 C31 C27 C26 0.6(4) . . . . ?
C32 C31 C27 C28 -177.5(3) . . . . ?
C23 C34 C33 C32 0.3(5) . . . . ?
C44 C36 C35 C31 -1.9(4) . . . . ?
C44 C36 C35 C40 -179.9(3) . . . . ?
C44 C36 C37 C38 179.6(3) . . . . ?
C44 C36 C37 C41 0.7(4) . . . . ?
C44 C43 C42 C41 -1.0(6) . . . . ?
C26 N2 C25 C24 179.9(2) . . . . ?
C26 N2 C25 C32 0.3(4) . . . . ?
C26 C27 C28 O2 19.8(5) . . . . ?
C26 C30 C29 O2 -49.2(4) . . . . ?
C31 C35 C40 C39 -178.1(3) . . . . ?
C31 C32 C33 C34 179.6(3) . . . . ?
C31 C27 C28 O2 -162.1(3) . . . . ?
C38 C37 C41 C42 -179.2(3) . . . . ?
C33 C32 C31 C35 0.6(4) . . . . ?
C33 C32 C31 C27 179.7(3) . . . . ?
C40 C35 C31 C32 86.8(3) . . . . ?
C40 C35 C31 C27 -92.3(4) . . . . ?
C27 C26 C30 C29 17.5(4) . . . . ?
C41 C37 C38 C39 179.6(3) . . . . ?
C28 O2 C29 C30 68.7(4) . . . . ?
C30 C26 C27 C31 178.8(3) . . . . ?
C30 C26 C27 C28 -3.0(4) . . . . ?
C29 O2 C28 C27 -52.2(4) . . . . ?

_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 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.826
