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

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

data_prm3_red
_database_code_depnum_ccdc_archive 'CCDC 2073287'
loop_
_audit_author_name
_audit_author_address
'Shinya Matsumoto'
;Yokohama National University
Japan
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-19
_audit_creation_method           
;
Olex2 1.2
(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         'C21 H16 Cl2 N2 O2'
_chemical_formula_sum            'C21 H16 Cl2 N2 O2'
_chemical_formula_weight         399.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H16O2N2Cl2
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1089(2)
_cell_length_b                   9.6567(5)
_cell_length_c                   15.8773(6)
_cell_angle_alpha                87.008(4)
_cell_angle_beta                 88.263(3)
_cell_angle_gamma                88.159(3)
_cell_volume                     934.49(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4345
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      72.3800
_cell_measurement_theta_min      4.5950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8759
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.689
_diffrn_reflns_theta_min         4.587
_diffrn_ambient_temperature      223(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     55.00  88.00   0.50    1.27    --    0.00  38.00-150.00   66
  2  ω     54.00  89.00   0.50    1.27    --    0.00  38.00   0.00   70
  3  ω     -3.00  23.00   0.50    1.27    --    0.00  38.00   0.00   52
  4  ω    -29.00   9.00   0.50    1.27    --    0.00  77.00 -60.00   76
  5  ω     18.00  48.00   0.50    1.27    --    0.00  77.00 -60.00   60
  6  ω     51.00  86.00   0.50    1.27    --    0.00  77.00 -60.00   70
  7  ω    -14.00  19.00   0.50    1.27    --    0.00  38.00-150.00   66
  8  ω     87.00 112.00   0.50    5.07    --   92.40 -82.00  60.00   50
  9  ω     10.00  58.00   0.50    5.07    --   92.40 -82.00  60.00   96
 10  ω      6.00  37.00   0.50    5.07    --   92.40 -30.00 150.00   62
 11  ω     89.00 119.00   0.50    5.07    --   92.40 -82.00-150.00   60
 12  ω      4.00 108.00   0.50    5.07    --   92.40 -61.00 -90.00  208
 13  ω     10.00  52.00   0.50    5.07    --   92.40 -45.00   0.00   84
 14  ω     76.00 112.00   0.50    5.07    --   92.40 -45.00   0.00   72
 15  ω     31.00  65.00   0.50    5.07    --   92.40 -82.00-150.00   68
 16  ω      8.00 114.00   0.50    5.07    --   92.40 -61.00  60.00  212
 17  ω      3.00 107.00   0.50    5.07    --   92.40 -30.00  60.00  208
 18  ω     78.00 176.00   0.50    5.07    --   92.40  15.00-180.00  196
 19  ω     35.00  61.00   0.50    5.07    --   92.40 -45.00-120.00   52
 20  ω     72.00 107.00   0.50    5.07    --   92.40 -45.00-120.00   70
 21  ω     68.00 109.00   0.50    5.07    --   92.40 -82.00 150.00   82
 22  ω     11.00  83.00   0.50    5.07    --   92.40 -61.00-150.00  144
 23  ω     69.00 100.00   0.50    5.07    --   92.40 -30.00 150.00   62
 24  ω     68.00 122.00   0.50    5.07    --   92.40 -82.00 -30.00  108
 25  ω     16.00  42.00   0.50    5.07    --   92.40 -82.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0192014000
_diffrn_orient_matrix_UB_12      -0.1427086000
_diffrn_orient_matrix_UB_13      -0.0377638000
_diffrn_orient_matrix_UB_21      -0.0122035000
_diffrn_orient_matrix_UB_22      0.0708902000
_diffrn_orient_matrix_UB_23      -0.0890055000
_diffrn_orient_matrix_UB_31      0.2513891000
_diffrn_orient_matrix_UB_32      -0.0123703000
_diffrn_orient_matrix_UB_33      -0.0100048000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2887
_reflns_number_total             3600
_reflns_odcompleteness_completeness 99.04
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.597
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3600
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.011
_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)+(0.1022P)²+0.4341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1754
_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.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C20(H20), C21(H21), C17(H17), C18(H18), C10(H10), C11(H11), C14(H14),
 C13(H13)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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
Cl22 Cl 0.59174(12) -0.12882(7) 0.75033(5) 0.0540(2) Uani 1 1 d . . . . .
Cl15 Cl 0.23208(18) 0.91406(11) 0.02712(6) 0.0885(4) Uani 1 1 d . . . . .
O24 O 0.0890(3) 0.57404(18) 0.39848(11) 0.0455(4) Uani 1 1 d . . . . .
O23 O 0.9076(3) 0.23308(19) 0.36989(12) 0.0483(5) Uani 1 1 d . . . . .
N6 N 0.2480(3) 0.39384(19) 0.47886(13) 0.0370(5) Uani 1 1 d . . . . .
H6 H 0.146862 0.388993 0.517702 0.044 Uiso 1 1 calc R . . . .
N2 N 0.7432(3) 0.4080(2) 0.28550(14) 0.0406(5) Uani 1 1 d . . . . .
C16 C 0.4705(4) 0.2002(2) 0.54355(15) 0.0349(5) Uani 1 1 d . . . . .
C4 C 0.5574(4) 0.3492(2) 0.40740(15) 0.0358(5) Uani 1 1 d . . . . .
C8 C 0.4426(4) 0.4592(2) 0.36266(15) 0.0366(5) Uani 1 1 d . . . . .
C5 C 0.4350(4) 0.3085(2) 0.47838(15) 0.0351(5) Uani 1 1 d . . . . .
C7 C 0.2419(4) 0.4876(2) 0.40998(15) 0.0367(5) Uani 1 1 d . . . . .
C3 C 0.7540(4) 0.3164(2) 0.35833(16) 0.0387(5) Uani 1 1 d . . . . .
C1 C 0.5559(4) 0.4937(2) 0.28760(15) 0.0369(5) Uani 1 1 d . . . . .
C20 C 0.7068(4) 0.0208(2) 0.60826(17) 0.0422(6) Uani 1 1 d . . . . .
H20 H 0.838918 -0.029735 0.609472 0.051 Uiso 1 1 calc R . . . .
C19 C 0.5436(4) -0.0057(2) 0.66905(17) 0.0415(6) Uani 1 1 d . . . . .
C21 C 0.6700(4) 0.1235(2) 0.54574(16) 0.0399(5) Uani 1 1 d . . . . .
H21 H 0.778481 0.142058 0.504715 0.048 Uiso 1 1 calc R . . . .
C9 C 0.4878(4) 0.5958(3) 0.22162(16) 0.0416(6) Uani 1 1 d . . . . .
C17 C 0.3077(4) 0.1687(3) 0.60492(17) 0.0435(6) Uani 1 1 d . . . . .
H17 H 0.173716 0.217208 0.603627 0.052 Uiso 1 1 calc R . . . .
C25 C 0.9282(4) 0.4127(3) 0.22546(17) 0.0444(6) Uani 1 1 d . . . . .
H25A H 1.062342 0.397614 0.256236 0.053 Uiso 1 1 calc R . . . .
H25B H 0.931905 0.504924 0.198187 0.053 Uiso 1 1 calc R . . . .
C18 C 0.3440(4) 0.0662(3) 0.66735(18) 0.0481(6) Uani 1 1 d . . . . .
H18 H 0.235219 0.045674 0.707911 0.058 Uiso 1 1 calc R . . . .
C10 C 0.3355(5) 0.6976(3) 0.24264(17) 0.0480(6) Uani 1 1 d . . . . .
H10 H 0.285444 0.701692 0.298384 0.058 Uiso 1 1 calc R . . . .
C11 C 0.2552(5) 0.7940(3) 0.1827(2) 0.0554(7) Uani 1 1 d . . . . .
H11 H 0.150585 0.860670 0.198254 0.066 Uiso 1 1 calc R . . . .
C26 C 0.9236(5) 0.3079(3) 0.1582(2) 0.0567(7) Uani 1 1 d . . . . .
H26A H 0.783240 0.315280 0.131076 0.068 Uiso 1 1 calc R . . . .
H26B H 0.939588 0.215096 0.184170 0.068 Uiso 1 1 calc R . . . .
C12 C 0.3292(5) 0.7912(3) 0.1013(2) 0.0606(8) Uani 1 1 d . . . . .
C14 C 0.5488(6) 0.5887(4) 0.1360(2) 0.0692(9) Uani 1 1 d . . . . .
H14 H 0.643760 0.517476 0.119127 0.083 Uiso 1 1 calc R . . . .
C27 C 1.1063(6) 0.3309(4) 0.0921(2) 0.0725(10) Uani 1 1 d . . . . .
H27A H 1.108009 0.257912 0.053255 0.109 Uiso 1 1 calc GR . . . .
H27B H 1.244538 0.330650 0.119341 0.109 Uiso 1 1 calc GR . . . .
H27C H 1.081744 0.418577 0.062041 0.109 Uiso 1 1 calc GR . . . .
C13 C 0.4701(6) 0.6859(4) 0.0760(2) 0.0776(11) Uani 1 1 d . . . . .
H13 H 0.511961 0.680116 0.019497 0.093 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
Cl22 C19 1.734(2) . ?
Cl15 C12 1.731(3) . ?
O24 C7 1.244(3) . ?
O23 C3 1.228(3) . ?
N6 H6 0.8600 . ?
N6 C5 1.387(3) . ?
N6 C7 1.384(3) . ?
N2 C3 1.421(3) . ?
N2 C1 1.391(3) . ?
N2 C25 1.456(3) . ?
C16 C5 1.448(3) . ?
C16 C21 1.406(3) . ?
C16 C17 1.401(4) . ?
C4 C8 1.424(3) . ?
C4 C5 1.380(3) . ?
C4 C3 1.447(3) . ?
C8 C7 1.445(3) . ?
C8 C1 1.390(3) . ?
C1 C9 1.462(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.387(4) . ?
C20 C21 1.385(3) . ?
C19 C18 1.384(4) . ?
C21 H21 0.9300 . ?
C9 C10 1.378(4) . ?
C9 C14 1.404(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.511(4) . ?
C18 H18 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.385(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.358(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.522(4) . ?
C12 C13 1.379(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.387(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C13 H13 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
C5 N6 H6 123.7 . . ?
C7 N6 H6 123.7 . . ?
C7 N6 C5 112.6(2) . . ?
C3 N2 C25 119.4(2) . . ?
C1 N2 C3 111.5(2) . . ?
C1 N2 C25 128.7(2) . . ?
C21 C16 C5 120.2(2) . . ?
C17 C16 C5 121.1(2) . . ?
C17 C16 C21 118.7(2) . . ?
C8 C4 C3 107.4(2) . . ?
C5 C4 C8 109.1(2) . . ?
C5 C4 C3 143.4(2) . . ?
C4 C8 C7 107.3(2) . . ?
C1 C8 C4 109.6(2) . . ?
C1 C8 C7 143.0(2) . . ?
N6 C5 C16 121.5(2) . . ?
C4 C5 N6 106.5(2) . . ?
C4 C5 C16 132.1(2) . . ?
O24 C7 N6 123.0(2) . . ?
O24 C7 C8 132.4(2) . . ?
N6 C7 C8 104.61(19) . . ?
O23 C3 N2 122.3(2) . . ?
O23 C3 C4 133.0(2) . . ?
N2 C3 C4 104.63(19) . . ?
N2 C1 C9 126.3(2) . . ?
C8 C1 N2 106.8(2) . . ?
C8 C1 C9 126.9(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C21 C20 C19 119.0(2) . . ?
C20 C19 Cl22 119.51(19) . . ?
C18 C19 Cl22 119.1(2) . . ?
C18 C19 C20 121.4(2) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C10 C9 C1 118.2(2) . . ?
C10 C9 C14 117.2(2) . . ?
C14 C9 C1 124.2(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
N2 C25 H25A 108.6 . . ?
N2 C25 H25B 108.6 . . ?
N2 C25 C26 114.6(2) . . ?
H25A C25 H25B 107.6 . . ?
C26 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C19 C18 H18 120.3 . . ?
C17 C18 C19 119.5(3) . . ?
C17 C18 H18 120.3 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C25 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C25 C26 C27 111.3(3) . . ?
H26A C26 H26B 108.0 . . ?
C27 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
C11 C12 Cl15 119.8(2) . . ?
C11 C12 C13 120.4(3) . . ?
C13 C12 Cl15 119.6(3) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?

_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 2.264
_oxdiff_exptl_absorpt_empirical_full_min 0.481
####################################################################### 
# 
# 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_prm3v3rd
_database_code_depnum_ccdc_archive 'CCDC 2073289'
loop_
_audit_author_name
_audit_author_address
'Shinya Matsumoto'
;Yokohama National University
Japan
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-18
_audit_creation_method           
;
Olex2 1.2
(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         'C21 H16 Cl2 N2 O2'
_chemical_formula_sum            'C21 H16 Cl2 N2 O2'
_chemical_formula_weight         399.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H16O2N2Cl2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5775(9)
_cell_length_b                   7.9456(8)
_cell_length_c                   16.2096(13)
_cell_angle_alpha                103.927(8)
_cell_angle_beta                 96.226(8)
_cell_angle_gamma                104.186(10)
_cell_volume                     903.71(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2173
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      29.3770
_cell_measurement_theta_min      3.1650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.756
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.029
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14758
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.271
_diffrn_reflns_theta_min         3.238
_diffrn_ambient_temperature      223(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.870
_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 -15.00   0.50   27.09    --   -0.10 -82.00  60.00  148
  2  ω    -16.00  29.00   0.50   27.09    --   -0.10  77.00  60.00   90
  3  ω     49.00  77.00   0.50   27.09    --   -0.10  77.00  60.00   56
  4  ω    -84.00 -30.00   0.50   27.09    --   -0.10 -77.00-150.00  108
  5  ω    -45.00  27.00   0.50   27.09    --   -0.10 -77.00 -90.00  144
  6  ω    -67.00  81.00   0.50   27.09    --   -0.10   0.00 -90.00  296
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0651429000
_diffrn_orient_matrix_UB_12      -0.0590265000
_diffrn_orient_matrix_UB_13      0.0159541000
_diffrn_orient_matrix_UB_21      -0.0125669000
_diffrn_orient_matrix_UB_22      -0.0698038000
_diffrn_orient_matrix_UB_23      -0.0386507000
_diffrn_orient_matrix_UB_31      0.0722855000
_diffrn_orient_matrix_UB_32      -0.0287712000
_diffrn_orient_matrix_UB_33      0.0187234000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          '?crystal_description Value'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2746
_reflns_number_total             4700
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.349
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4700
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      0.998
_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)+(0.0727P)²+0.2850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1571
_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.a Secondary CH2 refined with riding coordinates:
 C00I(H00a,H00b), C00L(H00c,H00d)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00H(H00H), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q)
2.c Idealised Me refined as rotating group:
 C00R(H00e,H00f,H00g)
;
_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
Cl01 Cl -0.21168(10) 0.08628(11) 0.21592(5) 0.0484(2) Uani 1 1 d . . . . .
Cl02 Cl 0.99730(12) 1.32143(11) 1.04568(5) 0.0542(2) Uani 1 1 d . . . . .
O003 O 0.6144(3) 1.0426(3) 0.61501(12) 0.0417(5) Uani 1 1 d . . . . .
O004 O 0.2945(3) 0.2963(3) 0.63246(13) 0.0418(5) Uani 1 1 d . . . . .
N005 N 0.4821(3) 0.5611(3) 0.73050(13) 0.0317(5) Uani 1 1 d . . . . .
N006 N 0.4079(3) 0.7849(3) 0.52106(13) 0.0344(5) Uani 1 1 d . . . . .
H006 H 0.389904 0.828975 0.478383 0.041 Uiso 1 1 calc R . . . .
C007 C 0.3894(4) 0.5866(3) 0.59817(15) 0.0296(5) Uani 1 1 d . . . . .
C008 C 0.5627(3) 0.7380(3) 0.73129(15) 0.0284(5) Uani 1 1 d . . . . .
C009 C 0.1942(4) 0.4816(4) 0.44436(16) 0.0312(6) Uani 1 1 d . . . . .
C00A C 0.5238(4) 0.8849(4) 0.59977(16) 0.0314(6) Uani 1 1 d . . . . .
C00B C 0.3736(4) 0.4566(4) 0.64830(16) 0.0313(6) Uani 1 1 d . . . . .
C00C C 0.5093(3) 0.7546(3) 0.65027(15) 0.0288(5) Uani 1 1 d . . . . .
C00D C 0.8689(4) 1.1534(4) 0.95412(17) 0.0354(6) Uani 1 1 d . . . . .
C00E C 0.6695(4) 0.8801(3) 0.80875(15) 0.0296(5) Uani 1 1 d . . . . .
C00F C 0.3251(4) 0.6073(3) 0.51893(16) 0.0301(5) Uani 1 1 d . . . . .
C00G C -0.0559(4) 0.2389(4) 0.30430(17) 0.0352(6) Uani 1 1 d . . . . .
C00H C 0.1153(4) 0.3040(4) 0.44567(17) 0.0353(6) Uani 1 1 d . . . . .
H00H H 0.148389 0.267705 0.494129 0.042 Uiso 1 1 calc R . . . .
C00I C 0.3919(4) 0.4058(4) 0.84323(17) 0.0359(6) Uani 1 1 d . . . . .
H00A H 0.282125 0.321234 0.805015 0.043 Uiso 1 1 calc R . . . .
H00B H 0.357713 0.510514 0.873964 0.043 Uiso 1 1 calc R . . . .
C00J C 0.7993(4) 1.0288(4) 0.80061(17) 0.0336(6) Uani 1 1 d . . . . .
H00J H 0.819335 1.036807 0.745907 0.040 Uiso 1 1 calc R . . . .
C00K C 0.0197(4) 0.4119(4) 0.30107(17) 0.0386(6) Uani 1 1 d . . . . .
H00K H -0.012934 0.447071 0.252189 0.046 Uiso 1 1 calc R . . . .
C00L C 0.5379(4) 0.4633(4) 0.79064(16) 0.0340(6) Uani 1 1 d . . . . .
H00C H 0.650141 0.539932 0.829838 0.041 Uiso 1 1 calc R . . . .
H00D H 0.565948 0.356634 0.757906 0.041 Uiso 1 1 calc R . . . .
C00M C -0.0109(4) 0.1813(4) 0.37644(18) 0.0386(6) Uani 1 1 d . . . . .
H00M H -0.064194 0.063738 0.377939 0.046 Uiso 1 1 calc R . . . .
C00N C 0.7368(4) 1.0118(4) 0.96379(17) 0.0391(7) Uani 1 1 d . . . . .
H00N H 0.714321 1.007255 1.018603 0.047 Uiso 1 1 calc R . . . .
C00O C 0.9003(4) 1.1666(4) 0.87296(19) 0.0382(6) Uani 1 1 d . . . . .
H00O H 0.987492 1.265914 0.866937 0.046 Uiso 1 1 calc R . . . .
C00P C 0.1450(4) 0.5340(4) 0.37109(17) 0.0358(6) Uani 1 1 d . . . . .
H00P H 0.196683 0.651692 0.369217 0.043 Uiso 1 1 calc R . . . .
C00Q C 0.6360(4) 0.8743(4) 0.89164(16) 0.0345(6) Uani 1 1 d . . . . .
H00Q H 0.545771 0.777896 0.898253 0.041 Uiso 1 1 calc R . . . .
C00R C 0.4668(5) 0.3170(4) 0.90777(19) 0.0444(7) Uani 1 1 d . . . . .
H00E H 0.497801 0.211904 0.877091 0.067 Uiso 1 1 calc GR . . . .
H00F H 0.374243 0.282244 0.941226 0.067 Uiso 1 1 calc GR . . . .
H00G H 0.575288 0.401074 0.945506 0.067 Uiso 1 1 calc GR . . . .


_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
Cl01 C00G 1.735(3) . ?
Cl02 C00D 1.740(3) . ?
O003 C00A 1.223(3) . ?
O004 C00B 1.217(3) . ?
N005 C008 1.384(3) . ?
N005 C00B 1.427(3) . ?
N005 C00L 1.473(3) . ?
N006 C00A 1.399(3) . ?
N006 C00F 1.387(3) . ?
C007 C00B 1.451(4) . ?
C007 C00C 1.420(3) . ?
C007 C00F 1.385(3) . ?
C008 C00C 1.379(3) . ?
C008 C00E 1.468(3) . ?
C009 C00F 1.455(3) . ?
C009 C00H 1.397(4) . ?
C009 C00P 1.393(4) . ?
C00A C00C 1.458(4) . ?
C00D C00N 1.364(4) . ?
C00D C00O 1.386(4) . ?
C00E C00J 1.383(4) . ?
C00E C00Q 1.403(3) . ?
C00G C00K 1.370(4) . ?
C00G C00M 1.393(4) . ?
C00H C00M 1.381(4) . ?
C00I C00L 1.518(4) . ?
C00I C00R 1.529(4) . ?
C00J C00O 1.391(4) . ?
C00K C00P 1.384(4) . ?
C00N C00Q 1.388(4) . ?

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
C008 N005 C00B 111.9(2) . . ?
C008 N005 C00L 127.6(2) . . ?
C00B N005 C00L 117.7(2) . . ?
C00F N006 C00A 113.1(2) . . ?
C00C C007 C00B 108.5(2) . . ?
C00F C007 C00B 142.7(2) . . ?
C00F C007 C00C 108.8(2) . . ?
N005 C008 C00E 124.0(2) . . ?
C00C C008 N005 107.5(2) . . ?
C00C C008 C00E 128.3(2) . . ?
C00H C009 C00F 119.7(2) . . ?
C00P C009 C00F 121.5(2) . . ?
C00P C009 C00H 118.9(2) . . ?
O003 C00A N006 124.1(2) . . ?
O003 C00A C00C 132.6(2) . . ?
N006 C00A C00C 103.3(2) . . ?
O004 C00B N005 122.9(2) . . ?
O004 C00B C007 133.9(2) . . ?
N005 C00B C007 103.2(2) . . ?
C007 C00C C00A 108.2(2) . . ?
C008 C00C C007 108.9(2) . . ?
C008 C00C C00A 142.8(2) . . ?
C00N C00D Cl02 119.0(2) . . ?
C00N C00D C00O 121.1(2) . . ?
C00O C00D Cl02 119.8(2) . . ?
C00J C00E C008 120.0(2) . . ?
C00J C00E C00Q 118.5(2) . . ?
C00Q C00E C008 121.4(2) . . ?
N006 C00F C009 122.1(2) . . ?
C007 C00F N006 106.6(2) . . ?
C007 C00F C009 131.3(2) . . ?
C00K C00G Cl01 119.2(2) . . ?
C00K C00G C00M 121.9(2) . . ?
C00M C00G Cl01 118.9(2) . . ?
C00M C00H C009 121.3(3) . . ?
C00L C00I C00R 109.9(2) . . ?
C00E C00J C00O 121.0(2) . . ?
C00G C00K C00P 119.5(3) . . ?
N005 C00L C00I 113.7(2) . . ?
C00H C00M C00G 118.1(3) . . ?
C00D C00N C00Q 119.8(3) . . ?
C00D C00O C00J 119.0(3) . . ?
C00K C00P C009 120.3(3) . . ?
C00N C00Q C00E 120.4(3) . . ?

_olex2_submission_original_sample_id PRM3V
_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 2.430
_oxdiff_exptl_absorpt_empirical_full_min 0.573
####################################################################### 
# 
# 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_exp_582
_database_code_depnum_ccdc_archive 'CCDC 2073288'
loop_
_audit_author_name
_audit_author_address
'Shinya Matsumoto'
;Yokohama National University
Japan
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-19
_audit_creation_method           
;
Olex2 1.2
(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         'C21 H16 Cl2 N2 O2'
_chemical_formula_sum            'C21 H16 Cl2 N2 O2'
_chemical_formula_weight         399.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H16O2N2Cl2
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0941(2)
_cell_length_b                   10.1582(2)
_cell_length_c                   10.8283(3)
_cell_angle_alpha                63.183(2)
_cell_angle_beta                 70.379(2)
_cell_angle_gamma                80.704(2)
_cell_volume                     933.30(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5602
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      72.6990
_cell_measurement_theta_min      4.6710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -6 0 0.0331
0 6 0 0.0255
0 -6 -4 0.0155
-5 -1 2 0.0965
1 7 4 0.0256
0 -5 2 0.0420
0 5 -2 0.0305
5 5 5 0.1084
3 3 7 0.0787
0 0 6 0.0775
-5 -5 -1 0.0811
0 1 -6 0.0346

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.047
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
0.1804 -5.8131 0.1579 -0.5626 -0.4258 -0.7087
-0.1804 5.8131 -0.1579 0.5626 0.4258 0.7087
-0.3446 -6.4380 -4.0224 -0.0692 -0.8100 -0.5823
-5.2621 -1.1863 1.5149 0.0532 0.5957 -0.8015
0.6887 6.5101 3.9198 0.0656 0.7703 0.6342
0.3276 -4.9960 1.6891 -0.6866 -0.2377 -0.6871
-0.1314 5.0515 -1.5912 0.6666 0.2308 0.7088
4.8400 5.0131 4.6592 -0.4373 0.3055 0.8459
2.7486 2.6027 6.9864 -0.8061 0.5635 0.1807
0.1564 -0.1646 5.9563 -0.7602 0.5316 -0.3735
-4.5657 -4.8927 -1.4838 0.0383 -0.0266 -0.9989
0.3639 0.7079 -5.5348 0.7234 -0.5058 0.4699

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9702
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.109
_diffrn_reflns_theta_min         4.651
_diffrn_ambient_temperature      223(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  51.00   0.50    0.73    --    0.00  65.00 124.00   70
  2  ω    111.00 182.00   0.50    2.90    --   92.40  65.00 124.00  142
  3  ω     83.00 112.00   0.50    2.90    --   92.40 -65.00 -10.00   58
  4  ω     44.00  70.00   0.50    2.90    --   92.40 -65.00 -10.00   52
  5  ω    -62.00   1.00   0.50    0.73    --    0.00 -65.00 -10.00  126
  6  ω     29.00  56.00   0.50    0.73    --    0.00  38.00  90.00   54
  7  ω    -11.00  21.00   0.50    0.73    --    0.00 -57.00  90.00   64
  8  ω     40.00  80.00   0.50    0.73    --    0.00  19.00 -30.00   80
  9  ω    -60.00 -20.00   0.50    0.73    --    0.00 -57.00  90.00   80
 10  ω    -17.00  28.00   0.50    0.73    --    0.00  19.00 -30.00   90
 11  ω      3.00  61.00   0.50    2.90    --   92.40 -15.00   0.00  116
 12  ω      3.00  67.00   0.50    2.90    --   92.40 -77.00 -30.00  128
 13  ω      4.00  72.00   0.50    2.90    --   92.40 -30.00-180.00  136
 14  ω     67.00 102.00   0.50    2.90    --   92.40 -61.00  90.00   70
 15  ω     79.00 124.00   0.50    2.90    --   92.40 -82.00-180.00   90
 16  ω      8.00  53.00   0.50    2.90    --   92.40 -82.00 -90.00   90
 17  ω     57.00 124.00   0.50    2.90    --   92.40 -82.00 -90.00  134
 18  ω      9.00 105.00   0.50    2.90    --   92.40 -30.00 -30.00  192
 19  ω     76.00 123.00   0.50    2.90    --   92.40 -82.00  90.00   94
 20  ω     24.00  93.00   0.50    2.90    --   92.40 -45.00-120.00  138
 21  ω     11.00  41.00   0.50    2.90    --   92.40 -82.00-180.00   60
 22  ω      4.00  50.00   0.50    2.90    --   92.40 -61.00 120.00   92
 23  ω     64.00 123.00   0.50    2.90    --   92.40 -82.00   0.00  118
 24  ω      4.00  60.00   0.50    2.90    --   92.40 -61.00  90.00  112
 25  ω     82.00 108.00   0.50    2.90    --   92.40 -15.00   0.00   52
 26  ω     50.00  75.00   0.50    2.90    --   92.40 -82.00  90.00   50
 27  ω     20.00  88.00   0.50    2.90    --   92.40 -61.00-180.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0662174000
_diffrn_orient_matrix_UB_12      0.0913708000
_diffrn_orient_matrix_UB_13      -0.1233709000
_diffrn_orient_matrix_UB_21      -0.1025275000
_diffrn_orient_matrix_UB_22      0.0726154000
_diffrn_orient_matrix_UB_23      0.0939420000
_diffrn_orient_matrix_UB_31      0.1065847000
_diffrn_orient_matrix_UB_32      0.1235311000
_diffrn_orient_matrix_UB_33      -0.0620875000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3141
_reflns_number_total             3618
_reflns_odcompleteness_completeness 99.58
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.284
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.073
_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)+(0.0761P)²+0.1252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1289
_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.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C17(H17), C10(H10), C14(H14), C21(H21), C20(H20), C18(H18), C11(H11),
 C13(H13)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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
Cl22 Cl 0.98639(6) -0.09476(6) 0.22631(7) 0.0696(2) Uani 1 1 d . . . . .
Cl15 Cl 0.37916(8) 0.88194(7) 0.99717(7) 0.0830(2) Uani 1 1 d . . . . .
O24 O 0.84902(12) 0.55891(15) 0.61937(15) 0.0542(3) Uani 1 1 d . . . . .
O23 O 0.43008(12) 0.20575(15) 0.63031(14) 0.0532(3) Uani 1 1 d . . . . .
N6 N 0.86121(13) 0.38795(15) 0.52934(15) 0.0416(3) Uani 1 1 d . . . . .
H6 H 0.950894 0.389526 0.490476 0.050 Uiso 1 1 calc R . . . .
N2 N 0.41943(13) 0.37431(16) 0.72391(15) 0.0426(3) Uani 1 1 d . . . . .
C5 C 0.77180(16) 0.29967(18) 0.52559(17) 0.0393(3) Uani 1 1 d . . . . .
C8 C 0.64431(16) 0.43654(18) 0.64547(18) 0.0409(4) Uani 1 1 d . . . . .
C4 C 0.63739(16) 0.32817(18) 0.59872(17) 0.0404(3) Uani 1 1 d . . . . .
C9 C 0.47121(16) 0.56815(19) 0.78739(18) 0.0419(4) Uani 1 1 d . . . . .
C1 C 0.51144(16) 0.46464(18) 0.72096(17) 0.0408(3) Uani 1 1 d . . . . .
C16 C 0.82487(17) 0.20472(17) 0.45144(17) 0.0404(3) Uani 1 1 d . . . . .
C7 C 0.79018(16) 0.47311(19) 0.60248(18) 0.0428(4) Uani 1 1 d . . . . .
C17 C 0.96880(18) 0.1968(2) 0.38180(19) 0.0459(4) Uani 1 1 d . . . . .
H17 H 1.031891 0.253957 0.382097 0.055 Uiso 1 1 calc R . . . .
C3 C 0.49073(16) 0.28826(18) 0.64726(18) 0.0430(4) Uani 1 1 d . . . . .
C25 C 0.26564(15) 0.38933(19) 0.76194(18) 0.0440(4) Uani 1 1 d . . . . .
H25A H 0.236008 0.390881 0.684848 0.053 Uiso 1 1 calc R . . . .
H25B H 0.239349 0.483654 0.766302 0.053 Uiso 1 1 calc R . . . .
C10 C 0.36446(16) 0.5388(2) 0.91827(19) 0.0467(4) Uani 1 1 d . . . . .
H10 H 0.311993 0.453416 0.962477 0.056 Uiso 1 1 calc R . . . .
C14 C 0.54761(19) 0.69711(19) 0.7226(2) 0.0491(4) Uani 1 1 d . . . . .
H14 H 0.619197 0.718087 0.635690 0.059 Uiso 1 1 calc R . . . .
C21 C 0.73155(18) 0.11954(19) 0.44750(19) 0.0469(4) Uani 1 1 d . . . . .
H21 H 0.635700 0.124915 0.492002 0.056 Uiso 1 1 calc R . . . .
C20 C 0.78016(19) 0.0274(2) 0.3782(2) 0.0504(4) Uani 1 1 d . . . . .
H20 H 0.717799 -0.029000 0.375868 0.060 Uiso 1 1 calc R . . . .
C18 C 1.01751(19) 0.1050(2) 0.3129(2) 0.0498(4) Uani 1 1 d . . . . .
H18 H 1.113061 0.099849 0.267079 0.060 Uiso 1 1 calc R . . . .
C26 C 0.18593(17) 0.2692(2) 0.90417(19) 0.0474(4) Uani 1 1 d . . . . .
H26A H 0.220195 0.259207 0.981657 0.057 Uiso 1 1 calc R . . . .
H26B H 0.199975 0.175603 0.897442 0.057 Uiso 1 1 calc R . . . .
C11 C 0.33572(18) 0.6347(2) 0.9830(2) 0.0528(4) Uani 1 1 d . . . . .
H11 H 0.265387 0.613661 1.070706 0.063 Uiso 1 1 calc R . . . .
C19 C 0.9231(2) 0.0206(2) 0.3124(2) 0.0493(4) Uani 1 1 d . . . . .
C27 C 0.03038(18) 0.3105(2) 0.9362(2) 0.0563(5) Uani 1 1 d . . . . .
H27A H 0.000302 0.333266 0.853497 0.084 Uiso 1 1 calc GR . . . .
H27B H 0.015551 0.395057 0.957063 0.084 Uiso 1 1 calc GR . . . .
H27C H -0.022875 0.229229 1.018434 0.084 Uiso 1 1 calc GR . . . .
C13 C 0.5185(2) 0.7944(2) 0.7856(2) 0.0557(5) Uani 1 1 d . . . . .
H13 H 0.569462 0.880779 0.741086 0.067 Uiso 1 1 calc R . . . .
C12 C 0.4129(2) 0.7623(2) 0.9155(2) 0.0540(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl22 C19 1.7309(18) . ?
Cl15 C12 1.7348(19) . ?
O24 C7 1.237(2) . ?
O23 C3 1.2211(19) . ?
N6 H6 0.8600 . ?
N6 C5 1.3926(19) . ?
N6 C7 1.388(2) . ?
N2 C1 1.391(2) . ?
N2 C3 1.422(2) . ?
N2 C25 1.4675(19) . ?
C5 C4 1.382(2) . ?
C5 C16 1.451(2) . ?
C8 C4 1.423(2) . ?
C8 C1 1.378(2) . ?
C8 C7 1.443(2) . ?
C4 C3 1.453(2) . ?
C9 C1 1.462(2) . ?
C9 C10 1.398(2) . ?
C9 C14 1.392(2) . ?
C16 C17 1.403(2) . ?
C16 C21 1.401(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.516(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.382(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.385(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.521(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C12 1.383(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N6 H6 123.6 . . ?
C7 N6 H6 123.6 . . ?
C7 N6 C5 112.82(13) . . ?
C1 N2 C3 111.64(12) . . ?
C1 N2 C25 126.31(14) . . ?
C3 N2 C25 120.00(13) . . ?
N6 C5 C16 121.50(14) . . ?
C4 C5 N6 106.29(13) . . ?
C4 C5 C16 132.19(14) . . ?
C4 C8 C7 108.02(14) . . ?
C1 C8 C4 109.71(14) . . ?
C1 C8 C7 142.17(15) . . ?
C5 C4 C8 108.82(13) . . ?
C5 C4 C3 143.66(15) . . ?
C8 C4 C3 107.52(14) . . ?
C10 C9 C1 122.62(15) . . ?
C14 C9 C1 118.76(14) . . ?
C14 C9 C10 118.51(16) . . ?
N2 C1 C9 125.26(13) . . ?
C8 C1 N2 107.06(14) . . ?
C8 C1 C9 127.68(14) . . ?
C17 C16 C5 121.32(14) . . ?
C21 C16 C5 119.95(14) . . ?
C21 C16 C17 118.73(15) . . ?
O24 C7 N6 123.67(14) . . ?
O24 C7 C8 132.30(15) . . ?
N6 C7 C8 104.03(13) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.52(15) . . ?
C18 C17 H17 119.7 . . ?
O23 C3 N2 123.01(14) . . ?
O23 C3 C4 132.92(16) . . ?
N2 C3 C4 104.04(13) . . ?
N2 C25 H25A 108.5 . . ?
N2 C25 H25B 108.5 . . ?
N2 C25 C26 115.24(14) . . ?
H25A C25 H25B 107.5 . . ?
C26 C25 H25A 108.5 . . ?
C26 C25 H25B 108.5 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.00(17) . . ?
C11 C10 H10 119.5 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.85(16) . . ?
C13 C14 H14 119.6 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.87(16) . . ?
C20 C21 H21 119.6 . . ?
C21 C20 H20 120.6 . . ?
C19 C20 C21 118.88(16) . . ?
C19 C20 H20 120.6 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.47(16) . . ?
C19 C18 H18 120.3 . . ?
C25 C26 H26A 110.0 . . ?
C25 C26 H26B 110.0 . . ?
C25 C26 C27 108.60(15) . . ?
H26A C26 H26B 108.4 . . ?
C27 C26 H26A 110.0 . . ?
C27 C26 H26B 110.0 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.10(17) . . ?
C12 C11 H11 120.4 . . ?
C20 C19 Cl22 119.70(14) . . ?
C18 C19 Cl22 118.77(14) . . ?
C18 C19 C20 121.52(16) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C14 C13 H13 120.3 . . ?
C14 C13 C12 119.47(18) . . ?
C12 C13 H13 120.3 . . ?
C11 C12 Cl15 119.40(15) . . ?
C11 C12 C13 121.06(17) . . ?
C13 C12 Cl15 119.53(16) . . ?

_olex2_submission_original_sample_id PRM3O
_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 2.003
_oxdiff_exptl_absorpt_empirical_full_min 0.689
####################################################################### 
# 
# 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_prm3_turnorange
_database_code_depnum_ccdc_archive 'CCDC 2073290'
loop_
_audit_author_name
_audit_author_address
'Shinya Matsumoto'
;Yokohama National University
Japan
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-19
_audit_creation_method           
;
Olex2 1.2
(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         'C21 H16 Cl2 N2 O2'
_chemical_formula_sum            'C21 H16 Cl2 N2 O2'
_chemical_formula_weight         399.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H16O2N2Cl2
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0975(3)
_cell_length_b                   10.1452(4)
_cell_length_c                   10.8422(5)
_cell_angle_alpha                63.157(4)
_cell_angle_beta                 70.317(3)
_cell_angle_gamma                80.642(3)
_cell_volume                     933.03(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4976
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      72.0830
_cell_measurement_theta_min      4.6470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.483
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10831
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.424
_diffrn_reflns_theta_min         4.651
_diffrn_ambient_temperature      223(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  -3.00   0.50    0.99    --    0.00 -23.00 117.00  112
  2  ω     24.00  68.00   0.50    3.94    --   92.40 -23.00 117.00   88
  3  ω    119.00 179.00   0.50    3.94    --   92.40  23.00 -76.00  120
  4  ω     84.00 112.00   0.50    3.94    --   92.40  23.00 -76.00   56
  5  ω     31.00  87.00   0.50    0.99    --    0.00  77.00-120.00  112
  6  ω     50.00  88.00   0.50    0.99    --    0.00  23.00 -76.00   76
  7  ω    -77.00 -52.00   0.50    0.99    --    0.00 -57.00 -60.00   50
  8  ω     -1.00  24.00   0.50    0.99    --    0.00  77.00-120.00   50
  9  ω    -45.00  22.00   0.50    0.99    --    0.00 -57.00 -60.00  134
 10  ω      9.00  34.00   0.50    0.99    --    0.00  38.00 120.00   50
 11  ω      5.00 114.00   0.50    3.94    --   92.40 -61.00-150.00  218
 12  ω     67.00 106.00   0.50    3.94    --   92.40 -45.00 -60.00   78
 13  ω      5.00 124.00   0.50    3.94    --   92.40 -82.00-150.00  238
 14  ω     73.00 100.00   0.50    3.94    --   92.40 -82.00-180.00   54
 15  ω     78.00 103.00   0.50    3.94    --   92.40 -82.00-120.00   50
 16  ω     64.00 159.00   0.50    3.94    --   92.40  77.00  30.00  190
 17  ω     10.00 115.00   0.50    3.94    --   92.40 -61.00  60.00  210
 18  ω     57.00 122.00   0.50    3.94    --   92.40 -82.00 -60.00  130
 19  ω      4.00 116.00   0.50    3.94    --   92.40 -15.00-120.00  224
 20  ω     24.00  65.00   0.50    3.94    --   92.40 -45.00 -60.00   82
 21  ω    133.00 182.00   0.50    3.94    --   92.40  30.00-180.00   98
 22  ω     83.00 108.00   0.50    3.94    --   92.40  30.00-180.00   50
 23  ω     61.00  86.00   0.50    3.94    --   92.40 -77.00  60.00   50
 24  ω     97.00 122.00   0.50    3.94    --   92.40 -77.00  60.00   50
 25  ω     70.00 119.00   0.50    3.94    --   92.40 -82.00  90.00   98
 26  ω      5.00  30.00   0.50    3.94    --   92.40 -82.00  90.00   50
 27  ω     16.00 112.00   0.50    3.94    --   92.40 -45.00  60.00  192
 28  ω     75.00 100.00   0.50    3.94    --   92.40 -82.00   0.00   50
 29  ω     57.00  84.00   0.50    3.94    --   92.40 -77.00   0.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0452368000
_diffrn_orient_matrix_UB_12      0.0160101000
_diffrn_orient_matrix_UB_13      -0.1566887000
_diffrn_orient_matrix_UB_21      0.0173801000
_diffrn_orient_matrix_UB_22      0.1674816000
_diffrn_orient_matrix_UB_23      -0.0574603000
_diffrn_orient_matrix_UB_31      0.1546328000
_diffrn_orient_matrix_UB_32      -0.0257428000
_diffrn_orient_matrix_UB_33      -0.0000272000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2863
_reflns_number_total             3606
_reflns_odcompleteness_completeness 99.64
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.082
_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)+(0.0700P)²+0.1908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1359
_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.a Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b), C26(H26a,H26b)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C21(H21), C10(H10), C14(H14), C20(H20), C18(H18), C11(H11), C17(H17),
 C13(H13)
2.c Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl22 Cl 0.01359(8) 1.09498(8) 0.77357(8) 0.0749(2) Uani 1 1 d . . . . .
Cl15 Cl 0.62075(10) 0.11829(8) 0.00262(9) 0.0882(3) Uani 1 1 d . . . . .
O24 O 0.15086(15) 0.44114(19) 0.38067(18) 0.0588(4) Uani 1 1 d . . . . .
O23 O 0.56988(15) 0.79414(18) 0.36967(17) 0.0569(4) Uani 1 1 d . . . . .
N6 N 0.13880(17) 0.61184(19) 0.47124(18) 0.0464(4) Uani 1 1 d . . . . .
H6 H 0.049177 0.609902 0.510644 0.056 Uiso 1 1 calc R . . . .
N2 N 0.58092(16) 0.6255(2) 0.27579(18) 0.0464(4) Uani 1 1 d . . . . .
C8 C 0.3554(2) 0.5636(2) 0.3543(2) 0.0450(4) Uani 1 1 d . . . . .
C4 C 0.3627(2) 0.6716(2) 0.4015(2) 0.0447(4) Uani 1 1 d . . . . .
C16 C 0.1750(2) 0.7953(2) 0.5488(2) 0.0445(4) Uani 1 1 d . . . . .
C5 C 0.2279(2) 0.7003(2) 0.4743(2) 0.0442(4) Uani 1 1 d . . . . .
C9 C 0.5289(2) 0.4318(2) 0.2125(2) 0.0466(4) Uani 1 1 d . . . . .
C1 C 0.4887(2) 0.5353(2) 0.2794(2) 0.0448(4) Uani 1 1 d . . . . .
C3 C 0.5097(2) 0.7117(2) 0.3530(2) 0.0466(5) Uani 1 1 d . . . . .
C21 C 0.0313(2) 0.8031(2) 0.6180(2) 0.0500(5) Uani 1 1 d . . . . .
H21 H -0.031835 0.746330 0.617280 0.060 Uiso 1 1 calc R . . . .
C7 C 0.2099(2) 0.5266(2) 0.3976(2) 0.0474(5) Uani 1 1 d . . . . .
C10 C 0.6353(2) 0.4613(3) 0.0816(2) 0.0510(5) Uani 1 1 d . . . . .
H10 H 0.687611 0.546885 0.037309 0.061 Uiso 1 1 calc R . . . .
C25 C 0.7345(2) 0.6109(2) 0.2376(2) 0.0489(5) Uani 1 1 d . . . . .
H25A H 0.760959 0.516447 0.233154 0.059 Uiso 1 1 calc R . . . .
H25B H 0.763961 0.609154 0.314731 0.059 Uiso 1 1 calc R . . . .
C14 C 0.4527(2) 0.3023(2) 0.2776(2) 0.0526(5) Uani 1 1 d . . . . .
H14 H 0.381518 0.280929 0.364759 0.063 Uiso 1 1 calc R . . . .
C19 C 0.0768(2) 0.9796(2) 0.6873(2) 0.0530(5) Uani 1 1 d . . . . .
C20 C -0.0173(2) 0.8950(3) 0.6874(2) 0.0546(5) Uani 1 1 d . . . . .
H20 H -0.112724 0.899673 0.733942 0.065 Uiso 1 1 calc R . . . .
C18 C 0.2197(2) 0.9725(3) 0.6220(3) 0.0553(5) Uani 1 1 d . . . . .
H18 H 0.282063 1.028435 0.624731 0.066 Uiso 1 1 calc R . . . .
C11 C 0.6642(2) 0.3654(3) 0.0169(2) 0.0562(5) Uani 1 1 d . . . . .
H11 H 0.734597 0.386360 -0.070744 0.067 Uiso 1 1 calc R . . . .
C17 C 0.2683(2) 0.8806(2) 0.5523(2) 0.0509(5) Uani 1 1 d . . . . .
H17 H 0.364081 0.875475 0.507374 0.061 Uiso 1 1 calc R . . . .
C12 C 0.5871(3) 0.2382(3) 0.0844(3) 0.0580(6) Uani 1 1 d . . . . .
C26 C 0.8144(2) 0.7309(3) 0.0960(2) 0.0527(5) Uani 1 1 d . . . . .
H26A H 0.800635 0.824415 0.103065 0.063 Uiso 1 1 calc R . . . .
H26B H 0.779782 0.741543 0.018591 0.063 Uiso 1 1 calc R . . . .
C13 C 0.4817(3) 0.2055(3) 0.2144(3) 0.0604(6) Uani 1 1 d . . . . .
H13 H 0.430824 0.118948 0.258773 0.073 Uiso 1 1 calc R . . . .
C27 C 0.9699(2) 0.6896(3) 0.0630(3) 0.0609(6) Uani 1 1 d . . . . .
H27A H 1.023339 0.772764 -0.016078 0.091 Uiso 1 1 calc GR . . . .
H27B H 0.985118 0.608255 0.037070 0.091 Uiso 1 1 calc GR . . . .
H27C H 0.999332 0.661564 0.147041 0.091 Uiso 1 1 calc GR . . . .


_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
Cl22 C19 1.731(2) . ?
Cl15 C12 1.737(2) . ?
O24 C7 1.235(2) . ?
O23 C3 1.216(2) . ?
N6 H6 0.8600 . ?
N6 C5 1.388(2) . ?
N6 C7 1.392(2) . ?
N2 C1 1.388(3) . ?
N2 C3 1.426(3) . ?
N2 C25 1.465(2) . ?
C8 C4 1.423(3) . ?
C8 C1 1.379(3) . ?
C8 C7 1.441(3) . ?
C4 C5 1.385(3) . ?
C4 C3 1.457(3) . ?
C16 C5 1.453(3) . ?
C16 C21 1.399(3) . ?
C16 C17 1.398(3) . ?
C9 C1 1.465(3) . ?
C9 C10 1.397(3) . ?
C9 C14 1.393(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.383(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.513(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.378(3) . ?
C19 C20 1.379(3) . ?
C19 C18 1.383(3) . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(3) . ?
C17 H17 0.9300 . ?
C12 C13 1.382(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.521(3) . ?
C13 H13 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
C5 N6 H6 123.6 . . ?
C5 N6 C7 112.84(16) . . ?
C7 N6 H6 123.6 . . ?
C1 N2 C3 111.51(15) . . ?
C1 N2 C25 126.64(17) . . ?
C3 N2 C25 119.74(16) . . ?
C4 C8 C7 108.25(17) . . ?
C1 C8 C4 109.35(17) . . ?
C1 C8 C7 142.34(19) . . ?
C8 C4 C3 107.77(17) . . ?
C5 C4 C8 108.55(17) . . ?
C5 C4 C3 143.67(19) . . ?
C21 C16 C5 121.04(18) . . ?
C17 C16 C5 119.95(18) . . ?
C17 C16 C21 119.01(19) . . ?
N6 C5 C16 121.56(17) . . ?
C4 C5 N6 106.44(17) . . ?
C4 C5 C16 131.96(18) . . ?
C10 C9 C1 122.71(19) . . ?
C14 C9 C1 118.68(18) . . ?
C14 C9 C10 118.50(19) . . ?
N2 C1 C9 125.05(17) . . ?
C8 C1 N2 107.51(17) . . ?
C8 C1 C9 127.43(18) . . ?
O23 C3 N2 123.21(18) . . ?
O23 C3 C4 132.9(2) . . ?
N2 C3 C4 103.83(16) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.23(19) . . ?
C20 C21 H21 119.9 . . ?
O24 C7 N6 123.60(18) . . ?
O24 C7 C8 132.50(19) . . ?
N6 C7 C8 103.89(16) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.5 . . ?
N2 C25 H25A 108.4 . . ?
N2 C25 H25B 108.4 . . ?
N2 C25 C26 115.49(18) . . ?
H25A C25 H25B 107.5 . . ?
C26 C25 H25A 108.4 . . ?
C26 C25 H25B 108.4 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C20 C19 Cl22 118.81(18) . . ?
C20 C19 C18 121.5(2) . . ?
C18 C19 Cl22 119.67(17) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 C21 119.6(2) . . ?
C19 C20 H20 120.2 . . ?
C19 C18 H18 120.6 . . ?
C19 C18 C17 118.9(2) . . ?
C17 C18 H18 120.6 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.9(2) . . ?
C12 C11 H11 120.6 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C11 C12 Cl15 119.25(18) . . ?
C11 C12 C13 121.4(2) . . ?
C13 C12 Cl15 119.4(2) . . ?
C25 C26 H26A 109.9 . . ?
C25 C26 H26B 109.9 . . ?
C25 C26 C27 108.92(19) . . ?
H26A C26 H26B 108.3 . . ?
C27 C26 H26A 109.9 . . ?
C27 C26 H26B 109.9 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_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 1.986
_oxdiff_exptl_absorpt_empirical_full_min 0.505
