# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_3h
_database_code_depnum_ccdc_archive 'CCDC 1437686'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_date             2015-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H20 Cl N O6'
_chemical_formula_sum            'C21 H20 Cl N O6'
_chemical_formula_weight         417.83
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N1 O1'
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      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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.79637(17)
_cell_length_b                   13.3106(3)
_cell_length_c                   25.2934(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1951.47(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5810
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.2460
_cell_measurement_theta_min      4.7780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95169
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.0579
_exptl_crystal_size_mid          0.0409
_exptl_crystal_size_min          0.0215
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.737
_diffrn_reflns_theta_min         3.495
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -40.00    9.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -64.00  -14.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00   24.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  120.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega  -99.00  -73.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -32.00   -1.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -19.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega  -60.00   -2.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  125.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega -122.00  -41.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -19.0000  -60.0000 81

#__ type_ start__ end____ width___ exp.time_
  8 omega    9.00   67.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega    1.00   54.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013  -99.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   11.00  117.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000   60.0000 106

#__ type_ start__ end____ width___ exp.time_
 11 omega   11.00  114.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
 12 omega   80.00  105.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   11.00   72.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
 14 omega   43.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013 -125.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
 15 omega   74.00  174.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 16 omega   78.00  105.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   24.00  104.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
 18 omega   24.00   96.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
 19 omega   74.00  172.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
 20 omega   78.00  174.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
 21 omega   77.00  103.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   62.0000 -176.8667 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   80.00  129.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
 23 omega   36.00   86.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
 24 omega   78.00  104.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   74.00  100.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   33.00  116.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000  -60.0000 83

#__ type_ start__ end____ width___ exp.time_
 27 omega   81.00   85.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -30.0000 4
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2525942000
_diffrn_orient_matrix_UB_12      -0.0061741000
_diffrn_orient_matrix_UB_13      0.0186570000
_diffrn_orient_matrix_UB_21      -0.0799934000
_diffrn_orient_matrix_UB_22      -0.0094520000
_diffrn_orient_matrix_UB_23      -0.0579010000
_diffrn_orient_matrix_UB_31      0.0199832000
_diffrn_orient_matrix_UB_32      -0.1151414000
_diffrn_orient_matrix_UB_33      0.0037477000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3089
_reflns_number_total             3432
_reflns_odcompleteness_completeness 99.71
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.143
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1204 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.011(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.061
_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)+(0.0334P)²+0.0389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0697
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9), C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
Cl1 Cl 0.53179(14) 0.27171(6) 0.45124(3) 0.0399(2) Uani 1 1 d . . . . .
O1 O 0.2362(4) 0.93694(16) 0.44915(8) 0.0348(5) Uani 1 1 d . . . . .
O2 O 0.5225(4) 0.92182(15) 0.51253(7) 0.0321(5) Uani 1 1 d . . . . .
O3 O 1.0180(3) 0.82026(14) 0.28773(7) 0.0290(4) Uani 1 1 d . . . . .
O4 O 0.8918(4) 0.84176(18) 0.20847(8) 0.0427(6) Uani 1 1 d . . . . .
O5 O 0.0397(3) 0.59308(15) 0.24712(7) 0.0288(4) Uani 1 1 d . . . . .
O6 O 0.2632(3) 0.53882(15) 0.18015(7) 0.0291(5) Uani 1 1 d . . . . .
N1 N 0.8657(4) 0.81566(16) 0.25428(9) 0.0229(5) Uani 1 1 d . . . . .
C1 C 0.6379(5) 0.71329(19) 0.32054(10) 0.0193(5) Uani 1 1 d . . . . .
H1 H 0.7854 0.6773 0.3203 0.023 Uiso 1 1 calc R . . . .
C2 C 0.6165(4) 0.7682(2) 0.37259(10) 0.0193(5) Uani 1 1 d . . . . .
C3 C 0.7863(5) 0.7596(2) 0.41110(10) 0.0242(6) Uani 1 1 d . . . . .
H3 H 0.9145 0.7196 0.4042 0.029 Uiso 1 1 calc R . . . .
C4 C 0.7715(5) 0.8091(2) 0.46001(10) 0.0262(6) Uani 1 1 d . . . . .
H4 H 0.8859 0.8025 0.4855 0.031 Uiso 1 1 calc R . . . .
C5 C 0.5810(5) 0.8672(2) 0.46824(10) 0.0231(6) Uani 1 1 d . . . . .
C6 C 0.4097(5) 0.8760(2) 0.43040(10) 0.0227(6) Uani 1 1 d . . . . .
C7 C 0.4211(5) 0.8281(2) 0.38264(10) 0.0220(6) Uani 1 1 d . . . . .
H7 H 0.3040 0.8347 0.3577 0.026 Uiso 1 1 calc R . . . .
C8 C 0.3056(6) 0.9684(2) 0.50064(11) 0.0372(8) Uani 1 1 d . . . . .
H8A H 0.1908 0.9486 0.5265 0.045 Uiso 1 1 calc R . . . .
H8B H 0.3212 1.0409 0.5017 0.045 Uiso 1 1 calc R . . . .
C9 C 0.4422(5) 0.63637(18) 0.31069(9) 0.0193(5) Uani 1 1 d . . . . .
H9 H 0.2947 0.6687 0.3189 0.023 Uiso 1 1 calc R . . . .
C10 C 0.4643(5) 0.54294(19) 0.34445(9) 0.0194(5) Uani 1 1 d . . . . .
C11 C 0.6569(5) 0.4806(2) 0.34152(10) 0.0226(6) Uani 1 1 d . . . . .
H11 H 0.7734 0.4956 0.3175 0.027 Uiso 1 1 calc R . . . .
C12 C 0.6785(5) 0.3966(2) 0.37357(10) 0.0234(6) Uani 1 1 d . . . . .
H12 H 0.8085 0.3559 0.3714 0.028 Uiso 1 1 calc R . . . .
C13 C 0.5038(5) 0.37455(19) 0.40885(10) 0.0244(6) Uani 1 1 d . . . . .
C14 C 0.3102(5) 0.4339(2) 0.41275(11) 0.0272(6) Uani 1 1 d . . . . .
H14 H 0.1937 0.4181 0.4366 0.033 Uiso 1 1 calc R . . . .
C15 C 0.2917(5) 0.5180(2) 0.38043(10) 0.0247(6) Uani 1 1 d . . . . .
H15 H 0.1612 0.5584 0.3829 0.030 Uiso 1 1 calc R . . . .
C16 C 0.4523(5) 0.6174(2) 0.25085(9) 0.0211(5) Uani 1 1 d . . . . .
H16 H 0.5770 0.5703 0.2425 0.025 Uiso 1 1 calc R . . . .
C17 C 0.5056(5) 0.7222(2) 0.22715(10) 0.0279(6) Uani 1 1 d . . . . .
H17A H 0.6046 0.7160 0.1964 0.033 Uiso 1 1 calc R . . . .
H17B H 0.3642 0.7558 0.2167 0.033 Uiso 1 1 calc R . . . .
C18 C 0.6271(4) 0.7808(2) 0.27090(9) 0.0209(5) Uani 1 1 d . . . . .
H18 H 0.5340 0.8402 0.2793 0.025 Uiso 1 1 calc R . . . .
C19 C 0.2279(5) 0.5808(2) 0.22752(9) 0.0212(6) Uani 1 1 d . . . . .
C20 C 0.0585(5) 0.5226(2) 0.14718(11) 0.0299(7) Uani 1 1 d . . . . .
H20A H -0.0689 0.5002 0.1691 0.036 Uiso 1 1 calc R . . . .
H20B H 0.0902 0.4707 0.1212 0.036 Uiso 1 1 calc R . . . .
C21 C -0.0063(7) 0.6187(2) 0.11941(12) 0.0437(8) Uani 1 1 d . . . . .
H21A H 0.1165 0.6385 0.0962 0.066 Uiso 1 1 calc GR . . . .
H21B H -0.0323 0.6705 0.1451 0.066 Uiso 1 1 calc GR . . . .
H21C H -0.1445 0.6083 0.0992 0.066 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
Cl1 C13 1.746(3) . ?
O1 C6 1.377(3) . ?
O1 C8 1.426(3) . ?
O2 C5 1.378(3) . ?
O2 C8 1.433(4) . ?
O3 N1 1.224(3) . ?
O4 N1 1.219(3) . ?
O5 C19 1.210(3) . ?
O6 C19 1.338(3) . ?
O6 C20 1.466(3) . ?
N1 C18 1.518(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.511(3) . ?
C1 C9 1.548(4) . ?
C1 C18 1.546(3) . ?
C2 C3 1.390(4) . ?
C2 C7 1.408(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.404(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.367(4) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9800 . ?
C9 C10 1.514(3) . ?
C9 C16 1.536(3) . ?
C10 C11 1.393(4) . ?
C10 C15 1.392(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(4) . ?
C13 C14 1.376(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9800 . ?
C16 C17 1.549(4) . ?
C16 C19 1.509(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.527(4) . ?
C18 H18 0.9800 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.507(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C6 O1 C8 106.4(2) . . ?
C5 O2 C8 105.9(2) . . ?
C19 O6 C20 116.6(2) . . ?
O3 N1 C18 118.7(2) . . ?
O4 N1 O3 123.6(2) . . ?
O4 N1 C18 117.6(2) . . ?
C2 C1 H1 108.3 . . ?
C2 C1 C9 113.6(2) . . ?
C2 C1 C18 115.0(2) . . ?
C9 C1 H1 108.3 . . ?
C18 C1 H1 108.3 . . ?
C18 C1 C9 103.0(2) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 C7 119.3(2) . . ?
C7 C2 C1 119.8(2) . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.4(3) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.7(2) . . ?
C5 C4 H4 121.6 . . ?
O2 C5 C6 109.9(2) . . ?
C4 C5 O2 128.5(2) . . ?
C4 C5 C6 121.5(2) . . ?
O1 C6 C5 109.6(2) . . ?
C7 C6 O1 127.9(2) . . ?
C7 C6 C5 122.5(3) . . ?
C2 C7 H7 121.2 . . ?
C6 C7 C2 117.5(2) . . ?
C6 C7 H7 121.2 . . ?
O1 C8 O2 108.2(2) . . ?
O1 C8 H8A 110.1 . . ?
O1 C8 H8B 110.1 . . ?
O2 C8 H8A 110.1 . . ?
O2 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C1 C9 H9 108.3 . . ?
C10 C9 C1 113.0(2) . . ?
C10 C9 H9 108.3 . . ?
C10 C9 C16 114.7(2) . . ?
C16 C9 C1 103.9(2) . . ?
C16 C9 H9 108.3 . . ?
C11 C10 C9 121.8(2) . . ?
C15 C10 C9 120.3(2) . . ?
C15 C10 C11 117.9(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 Cl1 119.7(2) . . ?
C14 C13 Cl1 118.8(2) . . ?
C14 C13 C12 121.5(2) . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.9(3) . . ?
C15 C14 H14 120.6 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C9 C16 H16 110.2 . . ?
C9 C16 C17 103.9(2) . . ?
C17 C16 H16 110.2 . . ?
C19 C16 C9 114.0(2) . . ?
C19 C16 H16 110.2 . . ?
C19 C16 C17 108.2(2) . . ?
C16 C17 H17A 110.6 . . ?
C16 C17 H17B 110.6 . . ?
H17A C17 H17B 108.7 . . ?
C18 C17 C16 105.8(2) . . ?
C18 C17 H17A 110.6 . . ?
C18 C17 H17B 110.6 . . ?
N1 C18 C1 111.5(2) . . ?
N1 C18 C17 112.1(2) . . ?
N1 C18 H18 108.4 . . ?
C1 C18 H18 108.4 . . ?
C17 C18 C1 108.1(2) . . ?
C17 C18 H18 108.4 . . ?
O5 C19 O6 124.1(2) . . ?
O5 C19 C16 125.0(2) . . ?
O6 C19 C16 110.7(2) . . ?
O6 C20 H20A 109.7 . . ?
O6 C20 H20B 109.7 . . ?
O6 C20 C21 110.0(2) . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 H20A 109.7 . . ?
C21 C20 H20B 109.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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 C13 C14 C15 177.6(2) . . . . ?
O1 C6 C7 C2 -179.2(3) . . . . ?
O2 C5 C6 O1 0.2(3) . . . . ?
O2 C5 C6 C7 -179.0(2) . . . . ?
O3 N1 C18 C1 -25.4(3) . . . . ?
O3 N1 C18 C17 -146.6(2) . . . . ?
O4 N1 C18 C1 157.8(2) . . . . ?
O4 N1 C18 C17 36.5(3) . . . . ?
C1 C2 C3 C4 -179.6(2) . . . . ?
C1 C2 C7 C6 179.8(2) . . . . ?
C1 C9 C10 C11 -60.1(3) . . . . ?
C1 C9 C10 C15 118.7(3) . . . . ?
C1 C9 C16 C17 -38.5(3) . . . . ?
C1 C9 C16 C19 -156.0(2) . . . . ?
C2 C1 C9 C10 -73.2(3) . . . . ?
C2 C1 C9 C16 161.9(2) . . . . ?
C2 C1 C18 N1 90.9(3) . . . . ?
C2 C1 C18 C17 -145.5(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C2 C7 C6 0.6(4) . . . . ?
C3 C4 C5 O2 178.9(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 O1 178.7(2) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 O2 C8 O1 1.8(3) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C6 O1 C8 O2 -1.7(3) . . . . ?
C7 C2 C3 C4 -0.4(4) . . . . ?
C8 O1 C6 C5 0.9(3) . . . . ?
C8 O1 C6 C7 -179.9(3) . . . . ?
C8 O2 C5 C4 -179.6(3) . . . . ?
C8 O2 C5 C6 -1.3(3) . . . . ?
C9 C1 C2 C3 118.2(3) . . . . ?
C9 C1 C2 C7 -61.0(3) . . . . ?
C9 C1 C18 N1 -145.0(2) . . . . ?
C9 C1 C18 C17 -21.4(3) . . . . ?
C9 C10 C11 C12 178.3(2) . . . . ?
C9 C10 C15 C14 -178.5(2) . . . . ?
C9 C16 C17 C18 25.0(3) . . . . ?
C9 C16 C19 O5 22.2(4) . . . . ?
C9 C16 C19 O6 -162.2(2) . . . . ?
C10 C9 C16 C17 -162.3(2) . . . . ?
C10 C9 C16 C19 80.2(3) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C10 C15 C14 0.4(4) . . . . ?
C11 C12 C13 Cl1 -177.8(2) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C10 0.0(4) . . . . ?
C15 C10 C11 C12 -0.6(4) . . . . ?
C16 C9 C10 C11 58.7(3) . . . . ?
C16 C9 C10 C15 -122.5(3) . . . . ?
C16 C17 C18 N1 121.2(2) . . . . ?
C16 C17 C18 C1 -2.0(3) . . . . ?
C17 C16 C19 O5 -92.8(3) . . . . ?
C17 C16 C19 O6 82.8(3) . . . . ?
C18 C1 C2 C3 -123.5(3) . . . . ?
C18 C1 C2 C7 57.3(3) . . . . ?
C18 C1 C9 C10 161.7(2) . . . . ?
C18 C1 C9 C16 36.8(2) . . . . ?
C19 O6 C20 C21 81.3(3) . . . . ?
C19 C16 C17 C18 146.4(2) . . . . ?
C20 O6 C19 O5 10.3(4) . . . . ?
C20 O6 C19 C16 -165.3(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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 -9 1 0.0199 0.0006 -8.9953 0.9985 0.0740 0.0272 1.0395
0 9 -1 0.0148 -0.0006 8.9953 -0.9985 -0.0740 -0.0272 -1.0395
-4 0 0 0.0214 -3.9979 -0.0029 -0.0135 1.0096 0.3206 -0.0796
4 -1 0 0.0348 3.9980 -0.9966 0.0133 -1.0035 -0.3112 0.1947
0 -6 -12 0.0128 0.0043 -5.9930 -12.0113 -0.1882 0.7518 0.6451
0 7 11 0.0070 -0.0041 6.9927 11.0107 0.1633 -0.7033 -0.7640
0 -4 15 0.0169 -0.0042 -4.0023 15.0112 0.3058 -0.8310 0.5170
0 2 -16 0.0192 0.0047 2.0038 -16.0125 -0.3123 0.9078 -0.2906

_olex2_submission_special_instructions 'No special instructions were received'

