# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_xnkd-1109-1
_database_code_depnum_ccdc_archive 'CCDC 1448025'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;
_audit_creation_date             2016-09-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        'AP/B18C6 cocrystal'
_chemical_formula_moiety         'Cl O4, C16 H24 O6, H4 N'
_chemical_formula_sum            'C16 H28 Cl N O10'
_chemical_formula_weight         429.84
_chemical_melting_point          414.25
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.2783(2)
_cell_length_b                   9.93551(15)
_cell_length_c                   14.7043(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.5877(17)
_cell_angle_gamma                90
_cell_volume                     2056.85(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4368
_cell_measurement_temperature    292.36(10)
_cell_measurement_theta_max      72.2100
_cell_measurement_theta_min      5.3750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56120
_exptl_absorpt_correction_type   multi-scan
_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.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11060
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.046
_diffrn_reflns_theta_max         67.046
_diffrn_reflns_theta_min         4.728
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.36(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   53.00   1.0000    1.5800
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00  104.00   1.0000    1.5800
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   75.00   1.0000    1.5800
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   63.00   1.0000    1.5800
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -77.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00  104.00   1.0000    1.5800
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   10.00  104.00   1.0000    1.5800
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000   60.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00  109.00   1.0000    6.3100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000    6.3100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   98.00   1.0000    6.3100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   91.00  176.00   1.0000    6.3100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000    6.3100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00  109.00   1.0000    6.3100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   91.00   1.0000    6.3100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00  135.00   1.0000    6.3100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
 15 omega   10.00  104.00   1.0000    1.5800
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
 16 omega  -33.00   55.00   1.0000    1.5800
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000  120.0000 88

#__ type_ start__ end____ width___ exp.time_
 17 omega  -33.00   55.00   1.0000    1.5800
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000   30.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0515869000
_diffrn_orient_matrix_UB_12      -0.0235504000
_diffrn_orient_matrix_UB_13      0.0993607000
_diffrn_orient_matrix_UB_21      -0.0963748000
_diffrn_orient_matrix_UB_22      -0.0207471000
_diffrn_orient_matrix_UB_23      0.0320351000
_diffrn_orient_matrix_UB_31      0.0051421000
_diffrn_orient_matrix_UB_32      -0.1518420000
_diffrn_orient_matrix_UB_33      -0.0197398000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3130
_reflns_number_total             3671
_reflns_odcompleteness_completeness 99.90
_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         0.758
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0706
_refine_ls_restrained_S_all      1.055
_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)+(0.1360P)²+0.8300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2059
_refine_ls_wR_factor_ref         0.2167
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N006-H
 0.98 with sigma of 0.02
 N006-H00Y
 0.98 with sigma of 0.02
 N006-HA
 0.98 with sigma of 0.02
 N006-HB
 0.85 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00E(H00C,H00D), C00H(H00E,H00H), C00I(H00I,H00J), C00J(H00K,
 H00L), C00O(H00Q,H00R), C00Q(H00S,H00T), C00R(H00U,H00V), C00S(H00W,H00X)
3.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00K(H00M), C00L(H00N)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.25183(5) -0.02326(7) 0.37451(5) 0.0631(3) Uani 1 1 d . . . . .
O002 O 0.45007(13) 0.3503(2) 0.62888(14) 0.0570(5) Uani 1 1 d . . . . .
O003 O 0.31943(15) 0.4907(2) 0.52641(15) 0.0608(5) Uani 1 1 d . . . . .
O004 O 0.40606(16) 0.1185(2) 0.72241(16) 0.0685(6) Uani 1 1 d . . . . .
O005 O 0.12501(15) 0.4159(3) 0.49199(14) 0.0695(6) Uani 1 1 d . . . . .
N006 N 0.27514(19) 0.2157(3) 0.56138(19) 0.0618(6) Uani 1 1 d D . . . .
O007 O 0.08082(17) 0.1675(4) 0.5692(2) 0.0935(9) Uani 1 1 d . . . . .
O008 O 0.3335(2) -0.0051(3) 0.4446(2) 0.0913(8) Uani 1 1 d . . . . .
O009 O 0.1934(3) 0.0885(4) 0.3702(3) 0.1162(12) Uani 1 1 d . . . . .
O00A O 0.2137(2) 0.0524(4) 0.7104(3) 0.1243(14) Uani 1 1 d . . . . .
C00B C 0.4717(2) 0.4839(3) 0.61856(19) 0.0534(6) Uani 1 1 d . . . . .
C00C C 0.4008(2) 0.5602(3) 0.56353(19) 0.0560(7) Uani 1 1 d . . . . .
C00D C 0.4875(2) 0.1272(3) 0.6786(2) 0.0673(8) Uani 1 1 d . . . . .
H00A H 0.4715 0.0976 0.6150 0.081 Uiso 1 1 calc R . . . .
H00B H 0.5373 0.0692 0.7099 0.081 Uiso 1 1 calc R . . . .
C00E C 0.5214(2) 0.2686(3) 0.6815(2) 0.0630(7) Uani 1 1 d . . . . .
H00C H 0.5341 0.3000 0.7449 0.076 Uiso 1 1 calc R . . . .
H00D H 0.5798 0.2743 0.6563 0.076 Uiso 1 1 calc R . . . .
C00F C 0.5548(2) 0.5449(4) 0.6578(2) 0.0674(8) Uani 1 1 d . . . . .
H00F H 0.6016 0.4952 0.6947 0.081 Uiso 1 1 calc R . . . .
C00G C 0.4156(3) 0.6944(3) 0.5497(3) 0.0720(9) Uani 1 1 d . . . . .
H00G H 0.3686 0.7455 0.5141 0.086 Uiso 1 1 calc R . . . .
C00H C 0.0458(3) 0.3320(4) 0.4555(3) 0.0816(11) Uani 1 1 d . . . . .
H00E H 0.0649 0.2671 0.4128 0.098 Uiso 1 1 calc R . . . .
H00H H -0.0049 0.3868 0.4222 0.098 Uiso 1 1 calc R . . . .
C00I C 0.2482(2) 0.5635(4) 0.4655(2) 0.0746(9) Uani 1 1 d . . . . .
H00I H 0.2765 0.6067 0.4175 0.090 Uiso 1 1 calc R . . . .
H00J H 0.2209 0.6327 0.4996 0.090 Uiso 1 1 calc R . . . .
C00J C 0.1730(2) 0.4684(4) 0.4236(2) 0.0755(10) Uani 1 1 d . . . . .
H00K H 0.1283 0.5147 0.3772 0.091 Uiso 1 1 calc R . . . .
H00L H 0.2014 0.3955 0.3938 0.091 Uiso 1 1 calc R . . . .
C00K C 0.5694(3) 0.6806(4) 0.6427(3) 0.0804(10) Uani 1 1 d . . . . .
H00M H 0.6260 0.7214 0.6691 0.096 Uiso 1 1 calc R . . . .
C00L C 0.5006(3) 0.7542(4) 0.5889(3) 0.0844(11) Uani 1 1 d . . . . .
H00N H 0.5109 0.8449 0.5784 0.101 Uiso 1 1 calc R . . . .
O00M O 0.2818(3) -0.0398(8) 0.2917(3) 0.188(3) Uani 1 1 d . . . . .
C00N C 0.0563(3) 0.0820(6) 0.6375(5) 0.0999(15) Uani 1 1 d . . . . .
C00O C 0.0115(2) 0.2610(5) 0.5318(3) 0.0825(11) Uani 1 1 d . . . . .
H00Q H 0.0004 0.3248 0.5788 0.099 Uiso 1 1 calc R . . . .
H00R H -0.0478 0.2152 0.5091 0.099 Uiso 1 1 calc R . . . .
O00P O 0.1998(4) -0.1324(5) 0.3905(6) 0.207(3) Uani 1 1 d . . . . .
C00Q C 0.3732(3) -0.0168(4) 0.7255(4) 0.0967(13) Uani 1 1 d . . . . .
H00S H 0.3621 -0.0544 0.6638 0.116 Uiso 1 1 calc R . . . .
H00T H 0.4212 -0.0710 0.7633 0.116 Uiso 1 1 calc R . . . .
C00R C 0.1330(4) -0.0094(6) 0.6719(4) 0.1094(16) Uani 1 1 d . . . . .
H00U H 0.1124 -0.0683 0.7174 0.131 Uiso 1 1 calc R . . . .
H00V H 0.1461 -0.0652 0.6214 0.131 Uiso 1 1 calc R . . . .
C00S C 0.2875(4) -0.0207(7) 0.7629(5) 0.130(2) Uani 1 1 d . . . . .
H00W H 0.2677 -0.1136 0.7667 0.156 Uiso 1 1 calc R . . . .
H00X H 0.2995 0.0155 0.8250 0.156 Uiso 1 1 calc R . . . .
H00Y H 0.293(3) 0.147(3) 0.522(3) 0.097(13) Uiso 1 1 d D . . . .
H H 0.302(3) 0.300(3) 0.550(3) 0.116(17) Uiso 1 1 d D . . . .
HA H 0.303(4) 0.191(6) 0.623(2) 0.14(2) Uiso 1 1 d D . . . .
H00O H 0.004(4) 0.042(5) 0.614(3) 0.106(16) Uiso 1 1 d . . . . .
H00P H 0.064(5) 0.121(8) 0.696(6) 0.17(3) Uiso 1 1 d . . . . .
HB H 0.2194(16) 0.242(5) 0.563(4) 0.125(19) Uiso 1 1 d 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
Cl01 O008 1.433(3) . ?
Cl01 O009 1.383(3) . ?
Cl01 O00M 1.366(4) . ?
Cl01 O00P 1.357(4) . ?
O002 C00B 1.377(4) . ?
O002 C00E 1.426(3) . ?
O003 C00C 1.383(4) . ?
O003 C00I 1.434(4) . ?
O004 C00D 1.423(4) . ?
O004 C00Q 1.427(5) . ?
O005 C00H 1.435(4) . ?
O005 C00J 1.408(4) . ?
N006 H00Y 0.962(19) . ?
N006 H 0.95(2) . ?
N006 HA 0.96(2) . ?
N006 HB 0.843(10) . ?
O007 C00N 1.403(6) . ?
O007 C00O 1.401(5) . ?
O00A C00R 1.344(6) . ?
O00A C00S 1.401(6) . ?
C00B C00C 1.407(4) . ?
C00B C00F 1.371(4) . ?
C00C C00G 1.371(5) . ?
C00D H00A 0.9700 . ?
C00D H00B 0.9700 . ?
C00D C00E 1.485(5) . ?
C00E H00C 0.9700 . ?
C00E H00D 0.9700 . ?
C00F H00F 0.9300 . ?
C00F C00K 1.388(5) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.388(6) . ?
C00H H00E 0.9700 . ?
C00H H00H 0.9700 . ?
C00H C00O 1.477(6) . ?
C00I H00I 0.9700 . ?
C00I H00J 0.9700 . ?
C00I C00J 1.484(6) . ?
C00J H00K 0.9700 . ?
C00J H00L 0.9700 . ?
C00K H00M 0.9300 . ?
C00K C00L 1.366(6) . ?
C00L H00N 0.9300 . ?
C00N C00R 1.448(8) . ?
C00N H00O 0.87(6) . ?
C00N H00P 0.93(8) . ?
C00O H00Q 0.9700 . ?
C00O H00R 0.9700 . ?
C00Q H00S 0.9700 . ?
C00Q H00T 0.9700 . ?
C00Q C00S 1.423(8) . ?
C00R H00U 0.9700 . ?
C00R H00V 0.9700 . ?
C00S H00W 0.9700 . ?
C00S H00X 0.9700 . ?

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
O009 Cl01 O008 110.11(19) . . ?
O00M Cl01 O008 108.5(2) . . ?
O00M Cl01 O009 109.3(3) . . ?
O00P Cl01 O008 112.3(3) . . ?
O00P Cl01 O009 107.8(3) . . ?
O00P Cl01 O00M 108.7(5) . . ?
C00B O002 C00E 117.1(2) . . ?
C00C O003 C00I 117.1(3) . . ?
C00D O004 C00Q 111.7(3) . . ?
C00J O005 C00H 113.3(3) . . ?
H00Y N006 H 112(4) . . ?
H00Y N006 HA 107(4) . . ?
H00Y N006 HB 126(5) . . ?
H N006 HA 106(4) . . ?
H N006 HB 98(5) . . ?
HA N006 HB 107(5) . . ?
C00O O007 C00N 115.9(3) . . ?
C00R O00A C00S 120.6(5) . . ?
O002 C00B C00C 115.4(3) . . ?
C00F C00B O002 125.1(3) . . ?
C00F C00B C00C 119.5(3) . . ?
O003 C00C C00B 115.7(3) . . ?
C00G C00C O003 124.6(3) . . ?
C00G C00C C00B 119.7(3) . . ?
O004 C00D H00A 109.8 . . ?
O004 C00D H00B 109.8 . . ?
O004 C00D C00E 109.3(3) . . ?
H00A C00D H00B 108.3 . . ?
C00E C00D H00A 109.8 . . ?
C00E C00D H00B 109.8 . . ?
O002 C00E C00D 108.9(2) . . ?
O002 C00E H00C 109.9 . . ?
O002 C00E H00D 109.9 . . ?
C00D C00E H00C 109.9 . . ?
C00D C00E H00D 109.9 . . ?
H00C C00E H00D 108.3 . . ?
C00B C00F H00F 119.8 . . ?
C00B C00F C00K 120.3(4) . . ?
C00K C00F H00F 119.8 . . ?
C00C C00G H00G 120.0 . . ?
C00C C00G C00L 120.1(4) . . ?
C00L C00G H00G 120.0 . . ?
O005 C00H H00E 109.8 . . ?
O005 C00H H00H 109.8 . . ?
O005 C00H C00O 109.5(3) . . ?
H00E C00H H00H 108.2 . . ?
C00O C00H H00E 109.8 . . ?
C00O C00H H00H 109.8 . . ?
O003 C00I H00I 109.9 . . ?
O003 C00I H00J 109.9 . . ?
O003 C00I C00J 109.1(3) . . ?
H00I C00I H00J 108.3 . . ?
C00J C00I H00I 109.9 . . ?
C00J C00I H00J 109.9 . . ?
O005 C00J C00I 110.1(3) . . ?
O005 C00J H00K 109.6 . . ?
O005 C00J H00L 109.6 . . ?
C00I C00J H00K 109.6 . . ?
C00I C00J H00L 109.6 . . ?
H00K C00J H00L 108.1 . . ?
C00F C00K H00M 120.0 . . ?
C00L C00K C00F 120.0(4) . . ?
C00L C00K H00M 120.0 . . ?
C00G C00L H00N 119.8 . . ?
C00K C00L C00G 120.4(3) . . ?
C00K C00L H00N 119.8 . . ?
O007 C00N C00R 111.5(4) . . ?
O007 C00N H00O 108(3) . . ?
O007 C00N H00P 114(5) . . ?
C00R C00N H00O 113(4) . . ?
C00R C00N H00P 88(5) . . ?
H00O C00N H00P 121(6) . . ?
O007 C00O C00H 108.2(3) . . ?
O007 C00O H00Q 110.0 . . ?
O007 C00O H00R 110.0 . . ?
C00H C00O H00Q 110.0 . . ?
C00H C00O H00R 110.0 . . ?
H00Q C00O H00R 108.4 . . ?
O004 C00Q H00S 109.6 . . ?
O004 C00Q H00T 109.6 . . ?
H00S C00Q H00T 108.1 . . ?
C00S C00Q O004 110.3(5) . . ?
C00S C00Q H00S 109.6 . . ?
C00S C00Q H00T 109.6 . . ?
O00A C00R C00N 113.9(5) . . ?
O00A C00R H00U 108.8 . . ?
O00A C00R H00V 108.8 . . ?
C00N C00R H00U 108.8 . . ?
C00N C00R H00V 108.8 . . ?
H00U C00R H00V 107.7 . . ?
O00A C00S C00Q 112.9(4) . . ?
O00A C00S H00W 109.0 . . ?
O00A C00S H00X 109.0 . . ?
C00Q C00S H00W 109.0 . . ?
C00Q C00S H00X 109.0 . . ?
H00W C00S H00X 107.8 . . ?

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
O002 C00B C00C O003 -0.7(3) . . . . ?
O002 C00B C00C C00G 179.6(3) . . . . ?
O002 C00B C00F C00K 179.8(3) . . . . ?
O003 C00C C00G C00L -178.9(3) . . . . ?
O003 C00I C00J O005 65.6(4) . . . . ?
O004 C00D C00E O002 -64.1(3) . . . . ?
O004 C00Q C00S O00A 61.0(7) . . . . ?
O005 C00H C00O O007 -68.6(4) . . . . ?
O007 C00N C00R O00A 60.3(7) . . . . ?
C00B O002 C00E C00D -175.7(2) . . . . ?
C00B C00C C00G C00L 0.9(5) . . . . ?
C00B C00F C00K C00L 0.4(5) . . . . ?
C00C O003 C00I C00J 172.7(2) . . . . ?
C00C C00B C00F C00K -0.7(5) . . . . ?
C00C C00G C00L C00K -1.2(5) . . . . ?
C00D O004 C00Q C00S -175.3(4) . . . . ?
C00E O002 C00B C00C 177.9(2) . . . . ?
C00E O002 C00B C00F -2.6(4) . . . . ?
C00F C00B C00C O003 179.8(3) . . . . ?
C00F C00B C00C C00G 0.0(4) . . . . ?
C00F C00K C00L C00G 0.6(5) . . . . ?
C00H O005 C00J C00I 174.9(3) . . . . ?
C00I O003 C00C C00B -176.3(3) . . . . ?
C00I O003 C00C C00G 3.4(4) . . . . ?
C00J O005 C00H C00O 169.1(3) . . . . ?
C00N O007 C00O C00H -174.5(4) . . . . ?
C00O O007 C00N C00R -179.4(5) . . . . ?
C00Q O004 C00D C00E -177.1(3) . . . . ?
C00R O00A C00S C00Q 118.9(6) . . . . ?
C00S O00A C00R C00N 167.2(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-09
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/methyl tert-butyl ether'
####################################################################### 
# 
# 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_xnkd-11-13-02
_database_code_depnum_ccdc_archive 'CCDC 1448026'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        'AP/DB18C6 cocrystal'
_chemical_formula_moiety         'Cl O4, 1.5(C20 H24 O6), H4 N'
_chemical_formula_sum            'C30 H40 Cl N O13'
_chemical_formula_weight         658.08
_chemical_melting_point          470.65
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6348(2)
_cell_length_b                   12.9180(2)
_cell_length_c                   20.7752(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.3603(17)
_cell_angle_gamma                90
_cell_volume                     3236.38(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8264
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      72.3030
_cell_measurement_theta_min      4.8080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66423
_exptl_absorpt_correction_type   multi-scan
_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.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19153
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.051
_diffrn_reflns_theta_max         67.051
_diffrn_reflns_theta_min         5.017
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   53.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00  104.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00  104.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   53.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00  104.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega    7.00  108.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -       36.5421   19.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
  7 omega   23.00   90.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000  -30.0000 67

#__ type_ start__ end____ width___ exp.time_
  8 omega   23.00   90.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
  9 omega    1.00   75.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
 10 omega  -31.00   53.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000   12.0400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   91.00   1.0000   12.0400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   91.00   1.0000   12.0400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   98.00   1.0000   12.0400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00  109.00   1.0000   12.0400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
 16 omega   40.00  135.00   1.0000   12.0400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00  116.00   1.0000   12.0400
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00   98.00   1.0000   12.0400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   98.00   1.0000   12.0400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 20 omega   39.00   64.00   1.0000   12.0400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1136508000
_diffrn_orient_matrix_UB_12      0.0130282000
_diffrn_orient_matrix_UB_13      -0.0122830000
_diffrn_orient_matrix_UB_21      -0.0338226000
_diffrn_orient_matrix_UB_22      -0.0796560000
_diffrn_orient_matrix_UB_23      -0.0577442000
_diffrn_orient_matrix_UB_31      -0.0475187000
_diffrn_orient_matrix_UB_32      0.0877588000
_diffrn_orient_matrix_UB_33      -0.0505278000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4734
_reflns_number_total             5551
_reflns_odcompleteness_completeness 95.63
_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         1.067
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5551
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0823
_refine_ls_restrained_S_all      1.049
_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)+(0.1769P)²+1.6310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2480
_refine_ls_wR_factor_ref         0.2600
_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 N(H,H) groups
2. Restrained distances
 N00B-HB
 0.85 with sigma of 0.01
3.a Free rotating group:
 N00B(H0AA,H)
3.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B), C00K(H00C,H00D), C00L(H00E,H00F), C00P(H00G,H00H), C00Q(H00Q,
 H00T), C00T(H00U,H00W), C00U(H00X,H00Y), C00W(H00I,H00J), C00X(H00,HC),
 C00Y(H00K,H00L), C013(H01A,H01B), C014(H01C,H01D)
3.c Aromatic/amide H refined with riding coordinates:
 C00I(H00P), C00M(H00M), C00N(H00N), C00O(H00O), C00R(H00R), C00S(H00S),
 C00V(H00V), C00Z(H00Z), C010(H010), C012(H012), C015(H015), C018(H018)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl01 Cl 0.82356(9) 0.00140(7) 0.61826(4) 0.0722(3) Uani 1 1 d . . . . .
O002 O 0.66939(17) 0.36974(17) 0.50536(10) 0.0538(5) Uani 1 1 d . . . . .
O003 O 0.79390(17) 0.32334(17) 0.74660(10) 0.0536(5) Uani 1 1 d . . . . .
O004 O 0.84238(16) 0.38885(18) 0.62797(10) 0.0529(5) Uani 1 1 d . . . . .
O005 O 0.60372(19) 0.24095(19) 0.74095(12) 0.0627(6) Uani 1 1 d . . . . .
O006 O 0.48348(18) 0.2750(2) 0.49739(12) 0.0621(6) Uani 1 1 d . . . . .
O007 O 0.8749(2) 0.67229(18) 0.46245(12) 0.0635(6) Uani 1 1 d . . . . .
O008 O 0.7978(2) 0.53405(18) 0.37156(11) 0.0671(7) Uani 1 1 d . . . . .
O009 O 1.0489(2) 0.6373(2) 0.59258(12) 0.0706(7) Uani 1 1 d . . . . .
O00A O 0.4450(2) 0.1998(2) 0.61703(14) 0.0736(7) Uani 1 1 d . . . . .
N00B N 0.6662(2) 0.2436(2) 0.61742(14) 0.0559(6) Uani 1 1 d D . . . .
H0AA H 0.6903 0.2439 0.6602 0.084 Uiso 1 1 d G . . . .
H H 0.6946 0.2938 0.6019 0.084 Uiso 1 1 d G . . . .
C00C C 0.5768(2) 0.4060(2) 0.45762(14) 0.0499(7) Uani 1 1 d . . . . .
C00D C 0.4769(3) 0.3546(3) 0.45323(15) 0.0538(7) Uani 1 1 d . . . . .
C00E C 0.8078(2) 0.6308(2) 0.34788(16) 0.0484(7) Uani 1 1 d . . . . .
C00F C 0.7576(3) 0.3387(2) 0.80208(15) 0.0528(7) Uani 1 1 d . . . . .
C00G C 0.6558(3) 0.2961(2) 0.79892(16) 0.0574(8) Uani 1 1 d . . . . .
C00H C 0.8971(2) 0.3687(3) 0.74711(16) 0.0545(7) Uani 1 1 d . . . . .
H00A H 0.9559 0.3442 0.7857 0.065 Uiso 1 1 calc R . . . .
H00B H 0.8930 0.4435 0.7500 0.065 Uiso 1 1 calc R . . . .
C00I C 0.7787(3) 0.6577(3) 0.28085(17) 0.0605(8) Uani 1 1 d . . . . .
H00P H 0.7505 0.6077 0.2480 0.073 Uiso 1 1 calc R . . . .
C00J C 0.8479(3) 0.7065(2) 0.39766(17) 0.0540(7) Uani 1 1 d . . . . .
C00K C 0.9204(2) 0.3382(3) 0.68293(16) 0.0539(7) Uani 1 1 d . . . . .
H00C H 0.9952 0.3583 0.6848 0.065 Uiso 1 1 calc R . . . .
H00D H 0.9139 0.2637 0.6770 0.065 Uiso 1 1 calc R . . . .
C00L C 0.7727(3) 0.4195(3) 0.51011(16) 0.0629(8) Uani 1 1 d . . . . .
H00E H 0.7682 0.4924 0.5201 0.075 Uiso 1 1 calc R . . . .
H00F H 0.7892 0.4134 0.4676 0.075 Uiso 1 1 calc R . . . .
C00M C 0.5768(3) 0.4877(3) 0.41489(17) 0.0616(8) Uani 1 1 d . . . . .
H00M H 0.6426 0.5223 0.4178 0.074 Uiso 1 1 calc R . . . .
C00N C 0.8175(4) 0.3917(3) 0.85980(17) 0.0674(9) Uani 1 1 d . . . . .
H00N H 0.8859 0.4207 0.8621 0.081 Uiso 1 1 calc R . . . .
C00O C 0.3812(3) 0.3871(3) 0.40574(18) 0.0688(10) Uani 1 1 d . . . . .
H00O H 0.3148 0.3535 0.4026 0.083 Uiso 1 1 calc R . . . .
C00P C 0.8614(3) 0.3690(3) 0.56472(16) 0.0623(8) Uani 1 1 d . . . . .
H00G H 0.8612 0.2950 0.5568 0.075 Uiso 1 1 calc R . . . .
H00H H 0.9332 0.3961 0.5652 0.075 Uiso 1 1 calc R . . . .
C00Q C 0.7992(4) 0.4463(3) 0.33061(17) 0.0709(10) Uani 1 1 d . . . . .
H00Q H 0.7681 0.4654 0.2836 0.085 Uiso 1 1 calc R . . . .
H00T H 0.7527 0.3926 0.3405 0.085 Uiso 1 1 calc R . . . .
C00R C 0.3818(3) 0.4683(4) 0.36282(19) 0.0770(11) Uani 1 1 d . . . . .
H00R H 0.3164 0.4887 0.3309 0.092 Uiso 1 1 calc R . . . .
C00S C 0.4788(4) 0.5184(3) 0.36747(19) 0.0711(10) Uani 1 1 d . . . . .
H00S H 0.4794 0.5735 0.3388 0.085 Uiso 1 1 calc R . . . .
C00T C 0.9221(3) 0.7452(3) 0.5148(2) 0.0714(10) Uani 1 1 d . . . . .
H00U H 0.8701 0.8011 0.5132 0.086 Uiso 1 1 calc R . . . .
H00W H 0.9891 0.7745 0.5087 0.086 Uiso 1 1 calc R . . . .
C00U C 1.0875(4) 0.5951(3) 0.65852(18) 0.0761(11) Uani 1 1 d . . . . .
H00X H 1.0383 0.5401 0.6636 0.091 Uiso 1 1 calc R . . . .
H00Y H 1.0885 0.6483 0.6916 0.091 Uiso 1 1 calc R . . . .
C00V C 0.6145(4) 0.3079(3) 0.8534(2) 0.0799(12) Uani 1 1 d . . . . .
H00V H 0.5458 0.2799 0.8514 0.096 Uiso 1 1 calc R . . . .
C00W C 0.3813(3) 0.2289(4) 0.4989(2) 0.0800(11) Uani 1 1 d . . . . .
H00I H 0.3447 0.1968 0.4558 0.096 Uiso 1 1 calc R . . . .
H00J H 0.3323 0.2813 0.5076 0.096 Uiso 1 1 calc R . . . .
C00X C 0.9481(3) 0.6917(4) 0.5804(2) 0.0766(11) Uani 1 1 d . . . . .
H00 H 0.9539 0.7419 0.6160 0.092 Uiso 1 1 calc R . . . .
HC H 0.8889 0.6437 0.5802 0.092 Uiso 1 1 calc R . . . .
C00Y C 0.4996(4) 0.1933(4) 0.7364(2) 0.0816(12) Uani 1 1 d . . . . .
H00K H 0.4443 0.2458 0.7356 0.098 Uiso 1 1 calc R . . . .
H00L H 0.5067 0.1490 0.7752 0.098 Uiso 1 1 calc R . . . .
C00Z C 0.7754(5) 0.4011(3) 0.9138(2) 0.0860(14) Uani 1 1 d . . . . .
H00Z H 0.8162 0.4351 0.9528 0.103 Uiso 1 1 calc R . . . .
C010 C 0.8591(4) 0.8064(3) 0.3775(3) 0.0855(13) Uani 1 1 d . . . . .
H010 H 0.8849 0.8579 0.4097 0.103 Uiso 1 1 calc R . . . .
O011 O 0.8190(5) -0.1053(4) 0.6295(3) 0.1514(19) Uani 1 1 d . . . . .
C012 C 0.6739(5) 0.3604(4) 0.9099(2) 0.0885(14) Uani 1 1 d . . . . .
H012 H 0.6450 0.3685 0.9458 0.106 Uiso 1 1 calc R . . . .
C013 C 0.4652(4) 0.1309(4) 0.6733(3) 0.0893(13) Uani 1 1 d . . . . .
H01A H 0.5233 0.0822 0.6726 0.107 Uiso 1 1 calc R . . . .
H01B H 0.3985 0.0921 0.6711 0.107 Uiso 1 1 calc R . . . .
C014 C 0.4064(4) 0.1496(4) 0.5533(2) 0.0892(13) Uani 1 1 d . . . . .
H01C H 0.3401 0.1100 0.5509 0.107 Uiso 1 1 calc R . . . .
H01D H 0.4626 0.1023 0.5477 0.107 Uiso 1 1 calc R . . . .
C015 C 0.7912(4) 0.7579(4) 0.2622(2) 0.0893(13) Uani 1 1 d . . . . .
H015 H 0.7715 0.7759 0.2168 0.107 Uiso 1 1 calc R . . . .
O016 O 0.8605(7) 0.0498(5) 0.6788(3) 0.184(3) Uani 1 1 d . . . . .
O017 O 0.7292(6) 0.0370(6) 0.5736(3) 0.197(3) Uani 1 1 d . . . . .
C018 C 0.8326(6) 0.8304(4) 0.3104(3) 0.1104(19) Uani 1 1 d . . . . .
H018 H 0.8430 0.8977 0.2976 0.133 Uiso 1 1 calc R . . . .
O019 O 0.9001(8) 0.0045(11) 0.5808(4) 0.274(6) Uani 1 1 d . . . . .
HA H 0.698(4) 0.189(3) 0.615(2) 0.069(12) Uiso 1 1 d . . . . .
HB H 0.5973(12) 0.247(5) 0.598(2) 0.108(18) Uiso 1 1 d 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
Cl01 O011 1.402(5) . ?
Cl01 O016 1.356(4) . ?
Cl01 O017 1.354(5) . ?
Cl01 O019 1.412(8) . ?
O002 C00C 1.371(4) . ?
O002 C00L 1.431(4) . ?
O003 C00F 1.376(4) . ?
O003 C00H 1.427(4) . ?
O004 C00K 1.425(4) . ?
O004 C00P 1.428(4) . ?
O005 C00G 1.385(4) . ?
O005 C00Y 1.430(5) . ?
O006 C00D 1.364(4) . ?
O006 C00W 1.431(4) . ?
O007 C00J 1.360(4) . ?
O007 C00T 1.427(4) . ?
O008 C00E 1.363(4) . ?
O008 C00Q 1.420(4) . ?
O009 C00U 1.419(5) . ?
O009 C00X 1.410(5) . ?
O00A C013 1.431(5) . ?
O00A C014 1.423(6) . ?
N00B H0AA 0.8496 . ?
N00B H 0.8497 . ?
N00B HA 0.83(5) . ?
N00B HB 0.844(10) . ?
C00C C00D 1.404(5) . ?
C00C C00M 1.379(5) . ?
C00D C00O 1.378(5) . ?
C00E C00I 1.374(5) . ?
C00E C00J 1.404(4) . ?
C00F C00G 1.382(5) . ?
C00F C00N 1.392(5) . ?
C00G C00V 1.389(5) . ?
C00H H00A 0.9700 . ?
C00H H00B 0.9700 . ?
C00H C00K 1.501(5) . ?
C00I H00P 0.9300 . ?
C00I C015 1.374(6) . ?
C00J C010 1.376(5) . ?
C00K H00C 0.9700 . ?
C00K H00D 0.9700 . ?
C00L H00E 0.9700 . ?
C00L H00F 0.9700 . ?
C00L C00P 1.487(5) . ?
C00M H00M 0.9300 . ?
C00M C00S 1.390(5) . ?
C00N H00N 0.9300 . ?
C00N C00Z 1.384(6) . ?
C00O H00O 0.9300 . ?
C00O C00R 1.378(6) . ?
C00P H00G 0.9700 . ?
C00P H00H 0.9700 . ?
C00Q H00Q 0.9700 . ?
C00Q H00T 0.9700 . ?
C00Q C00U 1.481(6) 3_766 ?
C00R H00R 0.9300 . ?
C00R C00S 1.364(7) . ?
C00S H00S 0.9300 . ?
C00T H00U 0.9700 . ?
C00T H00W 0.9700 . ?
C00T C00X 1.475(6) . ?
C00U C00Q 1.481(6) 3_766 ?
C00U H00X 0.9700 . ?
C00U H00Y 0.9700 . ?
C00V H00V 0.9300 . ?
C00V C012 1.370(7) . ?
C00W H00I 0.9700 . ?
C00W H00J 0.9700 . ?
C00W C014 1.487(7) . ?
C00X H00 0.9700 . ?
C00X HC 0.9700 . ?
C00Y H00K 0.9700 . ?
C00Y H00L 0.9700 . ?
C00Y C013 1.489(7) . ?
C00Z H00Z 0.9300 . ?
C00Z C012 1.365(7) . ?
C010 H010 0.9300 . ?
C010 C018 1.368(7) . ?
C012 H012 0.9300 . ?
C013 H01A 0.9700 . ?
C013 H01B 0.9700 . ?
C014 H01C 0.9700 . ?
C014 H01D 0.9700 . ?
C015 H015 0.9300 . ?
C015 C018 1.357(8) . ?
C018 H018 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
O011 Cl01 O019 100.9(6) . . ?
O016 Cl01 O011 108.6(4) . . ?
O016 Cl01 O019 113.3(6) . . ?
O017 Cl01 O011 112.1(4) . . ?
O017 Cl01 O016 117.9(5) . . ?
O017 Cl01 O019 102.8(5) . . ?
C00C O002 C00L 117.4(2) . . ?
C00F O003 C00H 117.8(2) . . ?
C00K O004 C00P 112.9(2) . . ?
C00G O005 C00Y 117.9(3) . . ?
C00D O006 C00W 117.0(3) . . ?
C00J O007 C00T 117.6(3) . . ?
C00E O008 C00Q 119.8(3) . . ?
C00X O009 C00U 113.4(3) . . ?
C014 O00A C013 113.9(3) . . ?
H0AA N00B H 109.5 . . ?
H0AA N00B HA 91.8 . . ?
H0AA N00B HB 119.2 . . ?
H N00B HA 111.5 . . ?
H N00B HB 105.8 . . ?
HA N00B HB 119(5) . . ?
O002 C00C C00D 116.2(3) . . ?
O002 C00C C00M 124.3(3) . . ?
C00M C00C C00D 119.5(3) . . ?
O006 C00D C00C 116.1(3) . . ?
O006 C00D C00O 125.1(3) . . ?
C00O C00D C00C 118.8(3) . . ?
O008 C00E C00I 124.9(3) . . ?
O008 C00E C00J 115.2(3) . . ?
C00I C00E C00J 119.9(3) . . ?
O003 C00F C00G 116.2(3) . . ?
O003 C00F C00N 124.1(3) . . ?
C00G C00F C00N 119.7(3) . . ?
O005 C00G C00V 124.6(4) . . ?
C00F C00G O005 116.1(3) . . ?
C00F C00G C00V 119.3(4) . . ?
O003 C00H H00A 110.1 . . ?
O003 C00H H00B 110.1 . . ?
O003 C00H C00K 107.8(2) . . ?
H00A C00H H00B 108.5 . . ?
C00K C00H H00A 110.1 . . ?
C00K C00H H00B 110.1 . . ?
C00E C00I H00P 119.8 . . ?
C015 C00I C00E 120.3(4) . . ?
C015 C00I H00P 119.8 . . ?
O007 C00J C00E 115.5(3) . . ?
O007 C00J C010 126.0(3) . . ?
C010 C00J C00E 118.5(3) . . ?
O004 C00K C00H 108.6(2) . . ?
O004 C00K H00C 110.0 . . ?
O004 C00K H00D 110.0 . . ?
C00H C00K H00C 110.0 . . ?
C00H C00K H00D 110.0 . . ?
H00C C00K H00D 108.4 . . ?
O002 C00L H00E 110.0 . . ?
O002 C00L H00F 110.0 . . ?
O002 C00L C00P 108.7(3) . . ?
H00E C00L H00F 108.3 . . ?
C00P C00L H00E 110.0 . . ?
C00P C00L H00F 110.0 . . ?
C00C C00M H00M 119.9 . . ?
C00C C00M C00S 120.2(4) . . ?
C00S C00M H00M 119.9 . . ?
C00F C00N H00N 120.0 . . ?
C00Z C00N C00F 120.0(4) . . ?
C00Z C00N H00N 120.0 . . ?
C00D C00O H00O 119.3 . . ?
C00R C00O C00D 121.5(4) . . ?
C00R C00O H00O 119.3 . . ?
O004 C00P C00L 109.1(3) . . ?
O004 C00P H00G 109.9 . . ?
O004 C00P H00H 109.9 . . ?
C00L C00P H00G 109.9 . . ?
C00L C00P H00H 109.9 . . ?
H00G C00P H00H 108.3 . . ?
O008 C00Q H00Q 109.1 . . ?
O008 C00Q H00T 109.1 . . ?
O008 C00Q C00U 112.4(3) . 3_766 ?
H00Q C00Q H00T 107.9 . . ?
C00U C00Q H00Q 109.1 3_766 . ?
C00U C00Q H00T 109.1 3_766 . ?
C00O C00R H00R 120.2 . . ?
C00S C00R C00O 119.6(3) . . ?
C00S C00R H00R 120.2 . . ?
C00M C00S H00S 119.8 . . ?
C00R C00S C00M 120.4(4) . . ?
C00R C00S H00S 119.8 . . ?
O007 C00T H00U 109.9 . . ?
O007 C00T H00W 109.9 . . ?
O007 C00T C00X 108.7(3) . . ?
H00U C00T H00W 108.3 . . ?
C00X C00T H00U 109.9 . . ?
C00X C00T H00W 109.9 . . ?
O009 C00U C00Q 108.9(3) . 3_766 ?
O009 C00U H00X 109.9 . . ?
O009 C00U H00Y 109.9 . . ?
C00Q C00U H00X 109.9 3_766 . ?
C00Q C00U H00Y 109.9 3_766 . ?
H00X C00U H00Y 108.3 . . ?
C00G C00V H00V 119.7 . . ?
C012 C00V C00G 120.6(5) . . ?
C012 C00V H00V 119.7 . . ?
O006 C00W H00I 110.0 . . ?
O006 C00W H00J 110.0 . . ?
O006 C00W C014 108.3(3) . . ?
H00I C00W H00J 108.4 . . ?
C014 C00W H00I 110.0 . . ?
C014 C00W H00J 110.0 . . ?
O009 C00X C00T 109.9(3) . . ?
O009 C00X H00 109.7 . . ?
O009 C00X HC 109.7 . . ?
C00T C00X H00 109.7 . . ?
C00T C00X HC 109.7 . . ?
H00 C00X HC 108.2 . . ?
O005 C00Y H00K 110.1 . . ?
O005 C00Y H00L 110.1 . . ?
O005 C00Y C013 108.1(3) . . ?
H00K C00Y H00L 108.4 . . ?
C013 C00Y H00K 110.1 . . ?
C013 C00Y H00L 110.1 . . ?
C00N C00Z H00Z 120.0 . . ?
C012 C00Z C00N 119.9(4) . . ?
C012 C00Z H00Z 120.0 . . ?
C00J C010 H010 119.8 . . ?
C018 C010 C00J 120.4(4) . . ?
C018 C010 H010 119.8 . . ?
C00V C012 H012 119.8 . . ?
C00Z C012 C00V 120.5(4) . . ?
C00Z C012 H012 119.8 . . ?
O00A C013 C00Y 108.5(4) . . ?
O00A C013 H01A 110.0 . . ?
O00A C013 H01B 110.0 . . ?
C00Y C013 H01A 110.0 . . ?
C00Y C013 H01B 110.0 . . ?
H01A C013 H01B 108.4 . . ?
O00A C014 C00W 109.3(4) . . ?
O00A C014 H01C 109.8 . . ?
O00A C014 H01D 109.8 . . ?
C00W C014 H01C 109.8 . . ?
C00W C014 H01D 109.8 . . ?
H01C C014 H01D 108.3 . . ?
C00I C015 H015 120.2 . . ?
C018 C015 C00I 119.6(4) . . ?
C018 C015 H015 120.2 . . ?
C010 C018 H018 119.4 . . ?
C015 C018 C010 121.2(4) . . ?
C015 C018 H018 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O002 C00C C00D O006 0.5(4) . . . . ?
O002 C00C C00D C00O -179.4(3) . . . . ?
O002 C00C C00M C00S 179.3(3) . . . . ?
O002 C00L C00P O004 -66.2(4) . . . . ?
O003 C00F C00G O005 1.5(4) . . . . ?
O003 C00F C00G C00V 179.5(3) . . . . ?
O003 C00F C00N C00Z -178.4(3) . . . . ?
O003 C00H C00K O004 68.8(3) . . . . ?
O005 C00G C00V C012 177.4(3) . . . . ?
O005 C00Y C013 O00A -65.3(5) . . . . ?
O006 C00D C00O C00R -179.8(3) . . . . ?
O006 C00W C014 O00A 68.1(5) . . . . ?
O007 C00J C010 C018 177.7(5) . . . . ?
O007 C00T C00X O009 80.2(4) . . . . ?
O008 C00E C00I C015 179.4(4) . . . . ?
O008 C00E C00J O007 2.2(4) . . . . ?
O008 C00E C00J C010 -179.3(3) . . . . ?
C00C O002 C00L C00P 179.7(3) . . . . ?
C00C C00D C00O C00R 0.1(5) . . . . ?
C00C C00M C00S C00R 0.1(5) . . . . ?
C00D O006 C00W C014 -176.0(3) . . . . ?
C00D C00C C00M C00S -0.5(5) . . . . ?
C00D C00O C00R C00S -0.5(6) . . . . ?
C00E O008 C00Q C00U 90.6(4) . . . 3_766 ?
C00E C00I C015 C018 0.0(7) . . . . ?
C00E C00J C010 C018 -0.6(7) . . . . ?
C00F O003 C00H C00K 178.0(2) . . . . ?
C00F C00G C00V C012 -0.5(5) . . . . ?
C00F C00N C00Z C012 -1.5(6) . . . . ?
C00G O005 C00Y C013 -174.8(3) . . . . ?
C00G C00F C00N C00Z 0.3(5) . . . . ?
C00G C00V C012 C00Z -0.7(6) . . . . ?
C00H O003 C00F C00G 178.2(2) . . . . ?
C00H O003 C00F C00N -3.0(4) . . . . ?
C00I C00E C00J O007 -179.7(3) . . . . ?
C00I C00E C00J C010 -1.3(5) . . . . ?
C00I C015 C018 C010 -1.9(9) . . . . ?
C00J O007 C00T C00X -178.3(3) . . . . ?
C00J C00E C00I C015 1.6(5) . . . . ?
C00J C010 C018 C015 2.3(9) . . . . ?
C00K O004 C00P C00L 176.7(3) . . . . ?
C00L O002 C00C C00D 178.9(3) . . . . ?
C00L O002 C00C C00M -0.9(4) . . . . ?
C00M C00C C00D O006 -179.7(3) . . . . ?
C00M C00C C00D C00O 0.4(4) . . . . ?
C00N C00F C00G O005 -177.3(3) . . . . ?
C00N C00F C00G C00V 0.7(5) . . . . ?
C00N C00Z C012 C00V 1.7(6) . . . . ?
C00O C00R C00S C00M 0.4(6) . . . . ?
C00P O004 C00K C00H 176.9(3) . . . . ?
C00Q O008 C00E C00I 25.7(5) . . . . ?
C00Q O008 C00E C00J -156.4(3) . . . . ?
C00T O007 C00J C00E 176.4(3) . . . . ?
C00T O007 C00J C010 -1.9(5) . . . . ?
C00U O009 C00X C00T 172.0(3) . . . . ?
C00W O006 C00D C00C 173.4(3) . . . . ?
C00W O006 C00D C00O -6.7(5) . . . . ?
C00X O009 C00U C00Q -171.7(3) . . . 3_766 ?
C00Y O005 C00G C00F 178.4(3) . . . . ?
C00Y O005 C00G C00V 0.5(5) . . . . ?
C013 O00A C014 C00W 176.4(4) . . . . ?
C014 O00A C013 C00Y -177.2(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-13
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: N, N-dimethylformamide/methyl tert-butyl ether'
####################################################################### 
# 
# 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_xnkj-cmm-3
_database_code_depnum_ccdc_archive 'CCDC 1448027'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-12-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            AP/18C6
_chemical_name_systematic        cocrystal
_chemical_formula_moiety         '2(Cl O4), 2(C12 H24 O6), 2(H4 N)'
_chemical_formula_sum            'C24 H56 Cl2 N2 O20'
_chemical_formula_weight         763.60
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   21.9447(9)
_cell_length_b                   8.6823(3)
_cell_length_c                   22.5551(11)
_cell_angle_alpha                90
_cell_angle_beta                 118.257(6)
_cell_angle_gamma                90
_cell_volume                     3785.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7247
_cell_measurement_temperature    176.41(10)
_cell_measurement_theta_max      70.8130
_cell_measurement_theta_min      5.5560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59697
_exptl_absorpt_correction_type   multi-scan
_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.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20336
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         3.873
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      176.41(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   70.00   1.0000    1.1600
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00   69.00   1.0000    1.1600
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   80.00   1.0000    4.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega   33.00  123.00   1.0000    4.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00  111.00   1.0000    4.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00  123.00   1.0000    4.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
  7 omega  -15.00   75.00   1.0000    4.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   82.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
 12 omega   36.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 80

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 80

#__ type_ start__ end____ width___ exp.time_
 14 omega   36.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 15 omega   82.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -180.0000 96

#__ type_ start__ end____ width___ exp.time_
 16 omega   40.00  130.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   30.0000 90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0079816000
_diffrn_orient_matrix_UB_12      0.0113863000
_diffrn_orient_matrix_UB_13      0.0641559000
_diffrn_orient_matrix_UB_21      -0.0776764000
_diffrn_orient_matrix_UB_22      0.0343984000
_diffrn_orient_matrix_UB_23      -0.0432965000
_diffrn_orient_matrix_UB_31      -0.0159125000
_diffrn_orient_matrix_UB_32      -0.1736910000
_diffrn_orient_matrix_UB_33      -0.0043573000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5631
_reflns_number_total             6762
_reflns_odcompleteness_completeness 99.92
_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         0.366
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         6762
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.041
_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)+(0.0970P)²+1.2160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1727
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 N00G-H00Z
 0.9 with sigma of 0.02
 N00G-HD
 0.82 with sigma of 0.02
3. Rigid bond restraints
 C011, C015
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C00U, C00X
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
4.a Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B), C00Q(H00C,H00D), C00R(H00E,H00F), C00S(H00G,H00H), C00T(H00I,
 H00J), C00V(H00K,H00L), C00W(H00M,H00N), C00X(H00S,H00T), C00Y(H00O,H00P),
 C00Z(H00U,H00V), C010(H01I,H01J), C011(H01A,H01B), C012(H01K,H01L), C013(H01C,
 H01D), C014(H01E,H01F), C016(H01M,H01N), C017(H01O,H01P), C018(H01Q,H01R),
 C019(H01S,H01T), C01A(H01U,H01V), C01B(H01W,H01X), C01C(H01Y,H)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl01 Cl 0.43640(3) 0.09024(8) 0.60071(3) 0.0619(2) Uani 1 1 d . . . . .
Cl02 Cl 0.10661(3) 0.66558(8) 0.43785(3) 0.0628(2) Uani 1 1 d . . . . .
O003 O 0.35195(10) 0.5206(2) 0.69123(10) 0.0654(5) Uani 1 1 d . . . . .
O004 O 0.27583(10) 0.2965(2) 0.59593(9) 0.0712(5) Uani 1 1 d . . . . .
O005 O 0.43879(10) 0.4106(2) 0.82567(10) 0.0677(5) Uani 1 1 d . . . . .
O006 O 0.31882(10) -0.0843(2) 0.76381(11) 0.0696(5) Uani 1 1 d . . . . .
O007 O 0.68331(10) 0.0401(2) 0.73768(11) 0.0716(5) Uani 1 1 d . . . . .
O008 O 0.61284(12) 0.4188(3) 0.55964(10) 0.0794(6) Uani 1 1 d . . . . .
O009 O 0.39849(10) 0.1384(2) 0.86356(9) 0.0701(5) Uani 1 1 d . . . . .
O00A O 0.23305(10) 0.0225(2) 0.62907(11) 0.0720(5) Uani 1 1 d . . . . .
O00B O 0.68952(11) 0.1493(2) 0.62201(11) 0.0740(6) Uani 1 1 d . . . . .
O00C O 0.65992(11) 0.2559(3) 0.81919(10) 0.0753(6) Uani 1 1 d . . . . .
O00D O 0.59646(10) 0.6412(2) 0.64068(13) 0.0815(6) Uani 1 1 d . . . . .
O00E O 0.58837(11) 0.5292(3) 0.75621(12) 0.0817(6) Uani 1 1 d . . . . .
N00F N 0.37078(15) 0.1772(3) 0.72289(14) 0.0570(5) Uani 1 1 d . . . . .
N00G N 0.59995(13) 0.3021(3) 0.67144(13) 0.0535(5) Uani 1 1 d D . . . .
O00H O 0.48983(12) 0.0621(3) 0.58322(13) 0.0855(6) Uani 1 1 d . . . . .
O00I O 0.17237(12) 0.6984(3) 0.44390(15) 0.1024(8) Uani 1 1 d . . . . .
O00J O 0.05804(14) 0.6420(3) 0.36871(12) 0.0981(8) Uani 1 1 d . . . . .
O00K O 0.37659(13) 0.1496(3) 0.54428(14) 0.0979(8) Uani 1 1 d . . . . .
O00L O 0.46037(14) 0.2027(4) 0.65242(16) 0.1271(12) Uani 1 1 d . . . . .
O00M O 0.41721(16) -0.0473(4) 0.62051(17) 0.1176(10) Uani 1 1 d . . . . .
O00N O 0.10864(16) 0.5304(4) 0.47300(17) 0.1367(13) Uani 1 1 d . . . . .
O00O O 0.08267(17) 0.7936(4) 0.45941(18) 0.1362(12) Uani 1 1 d . . . . .
C00P C 0.41530(16) 0.5908(3) 0.73952(19) 0.0786(9) Uani 1 1 d . . . . .
H00A H 0.4142 0.7001 0.7302 0.094 Uiso 1 1 calc R . . . .
H00B H 0.4539 0.5455 0.7360 0.094 Uiso 1 1 calc R . . . .
C00Q C 0.27716(19) 0.4539(4) 0.57821(15) 0.0767(8) Uani 1 1 d . . . . .
H00C H 0.2398 0.5099 0.5800 0.092 Uiso 1 1 calc R . . . .
H00D H 0.2707 0.4602 0.5326 0.092 Uiso 1 1 calc R . . . .
C00R C 0.34413(18) 0.5233(4) 0.62538(17) 0.0749(8) Uani 1 1 d . . . . .
H00E H 0.3815 0.4661 0.6242 0.090 Uiso 1 1 calc R . . . .
H00F H 0.3461 0.6287 0.6122 0.090 Uiso 1 1 calc R . . . .
C00S C 0.3988(2) -0.0241(4) 0.87648(16) 0.0805(9) Uani 1 1 d . . . . .
H00G H 0.4090 -0.0407 0.9228 0.097 Uiso 1 1 calc R . . . .
H00H H 0.4343 -0.0748 0.8695 0.097 Uiso 1 1 calc R . . . .
C00T C 0.42483(16) 0.5683(4) 0.80756(19) 0.0796(9) Uani 1 1 d . . . . .
H00I H 0.4630 0.6312 0.8390 0.096 Uiso 1 1 calc R . . . .
H00J H 0.3834 0.5998 0.8095 0.096 Uiso 1 1 calc R . . . .
C00U C 0.71372(19) 0.0280(4) 0.80742(19) 0.0878(9) Uani 1 1 d . U . . .
C00V C 0.46140(17) 0.2116(5) 0.90631(16) 0.0844(9) Uani 1 1 d . . . . .
H00K H 0.4979 0.1732 0.8976 0.101 Uiso 1 1 calc R . . . .
H00L H 0.4740 0.1906 0.9530 0.101 Uiso 1 1 calc R . . . .
C00W C 0.32982(19) -0.0896(4) 0.83004(19) 0.0801(9) Uani 1 1 d . . . . .
H00M H 0.3274 -0.1955 0.8425 0.096 Uiso 1 1 calc R . . . .
H00N H 0.2940 -0.0313 0.8337 0.096 Uiso 1 1 calc R . . . .
C00X C 0.6652(2) 0.0918(4) 0.82977(17) 0.0918(10) Uani 1 1 d . U . . .
H00S H 0.6200 0.0447 0.8044 0.110 Uiso 1 1 calc R . . . .
H00T H 0.6819 0.0694 0.8771 0.110 Uiso 1 1 calc R . . . .
C00Y C 0.45244(17) 0.3803(5) 0.89328(16) 0.0832(9) Uani 1 1 d . . . . .
H00O H 0.4143 0.4172 0.8997 0.100 Uiso 1 1 calc R . . . .
H00P H 0.4941 0.4340 0.9247 0.100 Uiso 1 1 calc R . . . .
C00Z C 0.6065(2) 0.5779(5) 0.54371(18) 0.1053(15) Uani 1 1 d . . . . .
H00U H 0.5854 0.5914 0.4953 0.126 Uiso 1 1 calc R . . . .
H00V H 0.6518 0.6255 0.5639 0.126 Uiso 1 1 calc R . . . .
C010 C 0.72540(16) -0.0263(4) 0.7112(2) 0.0882(11) Uani 1 1 d . . . . .
H01I H 0.7328 -0.1349 0.7225 0.106 Uiso 1 1 calc R . . . .
H01J H 0.7701 0.0243 0.7308 0.106 Uiso 1 1 calc R . . . .
C011 C 0.25375(16) -0.1513(3) 0.7165(2) 0.0815(9) Uani 1 1 d . U . . .
H01A H 0.2163 -0.1005 0.7201 0.098 Uiso 1 1 calc R . . . .
H01B H 0.2531 -0.2596 0.7267 0.098 Uiso 1 1 calc R . . . .
C012 C 0.69064(19) -0.0075(4) 0.6383(2) 0.0893(11) Uani 1 1 d . . . . .
H01K H 0.7148 -0.0661 0.6192 0.107 Uiso 1 1 calc R . . . .
H01L H 0.6437 -0.0463 0.6194 0.107 Uiso 1 1 calc R . . . .
C013 C 0.21823(19) 0.2143(5) 0.54791(16) 0.0879(10) Uani 1 1 d . . . . .
H01C H 0.2133 0.2310 0.5033 0.105 Uiso 1 1 calc R . . . .
H01D H 0.1764 0.2502 0.5481 0.105 Uiso 1 1 calc R . . . .
C014 C 0.22835(18) 0.0486(5) 0.56465(16) 0.0851(10) Uani 1 1 d . . . . .
H01E H 0.1899 -0.0095 0.5308 0.102 Uiso 1 1 calc R . . . .
H01F H 0.2704 0.0134 0.5648 0.102 Uiso 1 1 calc R . . . .
C015 C 0.24384(18) -0.1345(4) 0.6479(2) 0.0813(9) Uani 1 1 d . U . . .
C016 C 0.6532(2) 0.1735(5) 0.55073(18) 0.0995(13) Uani 1 1 d . . . . .
H01M H 0.6061 0.1364 0.5329 0.119 Uiso 1 1 calc R . . . .
H01N H 0.6755 0.1158 0.5295 0.119 Uiso 1 1 calc R . . . .
C017 C 0.6525(2) 0.3366(6) 0.53529(17) 0.0999(13) Uani 1 1 d . . . . .
H01O H 0.6994 0.3760 0.5562 0.120 Uiso 1 1 calc R . . . .
H01P H 0.6326 0.3506 0.4870 0.120 Uiso 1 1 calc R . . . .
C018 C 0.6132(2) 0.4943(6) 0.82638(19) 0.1044(14) Uani 1 1 d . . . . .
H01Q H 0.5844 0.5449 0.8424 0.125 Uiso 1 1 calc R . . . .
H01R H 0.6602 0.5314 0.8526 0.125 Uiso 1 1 calc R . . . .
C019 C 0.6111(2) 0.3257(6) 0.83440(17) 0.0965(12) Uani 1 1 d . . . . .
H01S H 0.6217 0.3014 0.8803 0.116 Uiso 1 1 calc R . . . .
H01T H 0.5652 0.2869 0.8044 0.116 Uiso 1 1 calc R . . . .
C01A C 0.5633(2) 0.6514(4) 0.5695(2) 0.1115(17) Uani 1 1 d . . . . .
H01U H 0.5558 0.7587 0.5560 0.134 Uiso 1 1 calc R . . . .
H01V H 0.5186 0.6007 0.5508 0.134 Uiso 1 1 calc R . . . .
C01B C 0.5917(2) 0.6875(4) 0.7426(3) 0.1114(16) Uani 1 1 d . . . . .
H01W H 0.6396 0.7197 0.7619 0.134 Uiso 1 1 calc R . . . .
H01X H 0.5693 0.7485 0.7628 0.134 Uiso 1 1 calc R . . . .
C01C C 0.5571(2) 0.7118(4) 0.6698(3) 0.1204(19) Uani 1 1 d . . . . .
H01Y H 0.5111 0.6673 0.6499 0.144 Uiso 1 1 calc R . . . .
H H 0.5525 0.8213 0.6602 0.144 Uiso 1 1 calc R . . . .
H00W H 0.400(2) 0.143(4) 0.7147(18) 0.081(11) Uiso 1 1 d . . . . .
H00Z H 0.6293(18) 0.234(4) 0.6958(19) 0.113(14) Uiso 1 1 d D . . . .
HA H 0.559(2) 0.259(5) 0.655(2) 0.109(14) Uiso 1 1 d . . . . .
H00X H 0.354(2) 0.099(5) 0.731(2) 0.108(15) Uiso 1 1 d . . . . .
H00Y H 0.388(2) 0.240(5) 0.752(2) 0.096(13) Uiso 1 1 d . . . . .
HB H 0.6074(19) 0.335(4) 0.6457(19) 0.078(12) Uiso 1 1 d . . . . .
HC H 0.339(3) 0.219(6) 0.689(3) 0.124(17) Uiso 1 1 d . . . . .
HD H 0.601(3) 0.381(4) 0.691(2) 0.14(2) Uiso 1 1 d D . . . .
H01G H 0.2854(19) -0.172(4) 0.6455(17) 0.084(10) Uiso 1 1 d . . . . .
H00Q H 0.7628(18) 0.092(4) 0.8309(16) 0.081(9) Uiso 1 1 d . . . . .
H01H H 0.196(2) -0.189(5) 0.611(2) 0.113(13) Uiso 1 1 d . . . . .
H00R H 0.7250(19) -0.083(5) 0.8217(18) 0.097(11) Uiso 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
Cl01 O00H 1.424(2) . ?
Cl01 O00K 1.424(3) . ?
Cl01 O00L 1.418(3) . ?
Cl01 O00M 1.408(3) . ?
Cl02 O00I 1.413(2) . ?
Cl02 O00J 1.427(3) . ?
Cl02 O00N 1.405(3) . ?
Cl02 O00O 1.411(3) . ?
O003 C00P 1.434(4) . ?
O003 C00R 1.412(4) . ?
O004 C00Q 1.428(4) . ?
O004 C013 1.408(4) . ?
O005 C00T 1.420(4) . ?
O005 C00Y 1.432(4) . ?
O006 C00W 1.396(4) . ?
O006 C011 1.440(4) . ?
O007 C00U 1.392(4) . ?
O007 C010 1.437(4) . ?
O008 C00Z 1.418(5) . ?
O008 C017 1.422(5) . ?
O009 C00S 1.440(4) . ?
O009 C00V 1.407(4) . ?
O00A C014 1.425(4) . ?
O00A C015 1.414(4) . ?
O00B C012 1.408(4) . ?
O00B C016 1.432(4) . ?
O00C C00X 1.441(4) . ?
O00C C019 1.407(4) . ?
O00D C01A 1.417(5) . ?
O00D C01C 1.446(5) . ?
O00E C018 1.441(5) . ?
O00E C01B 1.417(5) . ?
N00F H00W 0.80(4) . ?
N00F H00X 0.83(5) . ?
N00F H00Y 0.80(5) . ?
N00F HC 0.83(5) . ?
N00G H00Z 0.854(19) . ?
N00G HA 0.88(5) . ?
N00G HB 0.73(4) . ?
N00G HD 0.81(2) . ?
C00P H00A 0.9700 . ?
C00P H00B 0.9700 . ?
C00P C00T 1.460(5) . ?
C00Q H00C 0.9700 . ?
C00Q H00D 0.9700 . ?
C00Q C00R 1.474(5) . ?
C00R H00E 0.9700 . ?
C00R H00F 0.9700 . ?
C00S H00G 0.9700 . ?
C00S H00H 0.9700 . ?
C00S C00W 1.487(5) . ?
C00T H00I 0.9700 . ?
C00T H00J 0.9700 . ?
C00U C00X 1.485(6) . ?
C00U H00Q 1.10(3) . ?
C00U H00R 1.01(4) . ?
C00V H00K 0.9700 . ?
C00V H00L 0.9700 . ?
C00V C00Y 1.489(5) . ?
C00W H00M 0.9700 . ?
C00W H00N 0.9700 . ?
C00X H00S 0.9700 . ?
C00X H00T 0.9700 . ?
C00Y H00O 0.9700 . ?
C00Y H00P 0.9700 . ?
C00Z H00U 0.9700 . ?
C00Z H00V 0.9700 . ?
C00Z C01A 1.471(7) . ?
C010 H01I 0.9700 . ?
C010 H01J 0.9700 . ?
C010 C012 1.457(6) . ?
C011 H01A 0.9700 . ?
C011 H01B 0.9700 . ?
C011 C015 1.465(5) . ?
C012 H01K 0.9700 . ?
C012 H01L 0.9700 . ?
C013 H01C 0.9700 . ?
C013 H01D 0.9700 . ?
C013 C014 1.477(5) . ?
C014 H01E 0.9700 . ?
C014 H01F 0.9700 . ?
C015 H01G 0.99(4) . ?
C015 H01H 1.09(4) . ?
C016 H01M 0.9700 . ?
C016 H01N 0.9700 . ?
C016 C017 1.456(6) . ?
C017 H01O 0.9700 . ?
C017 H01P 0.9700 . ?
C018 H01Q 0.9700 . ?
C018 H01R 0.9700 . ?
C018 C019 1.478(6) . ?
C019 H01S 0.9700 . ?
C019 H01T 0.9700 . ?
C01A H01U 0.9700 . ?
C01A H01V 0.9700 . ?
C01B H01W 0.9700 . ?
C01B H01X 0.9700 . ?
C01B C01C 1.462(7) . ?
C01C H01Y 0.9700 . ?
C01C H 0.9700 . ?

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
O00K Cl01 O00H 110.25(16) . . ?
O00L Cl01 O00H 108.22(15) . . ?
O00L Cl01 O00K 108.2(2) . . ?
O00M Cl01 O00H 110.56(17) . . ?
O00M Cl01 O00K 107.66(18) . . ?
O00M Cl01 O00L 111.9(2) . . ?
O00I Cl02 O00J 109.57(17) . . ?
O00N Cl02 O00I 110.85(18) . . ?
O00N Cl02 O00J 107.7(2) . . ?
O00N Cl02 O00O 112.4(3) . . ?
O00O Cl02 O00I 109.7(2) . . ?
O00O Cl02 O00J 106.39(19) . . ?
C00R O003 C00P 112.5(2) . . ?
C013 O004 C00Q 113.5(3) . . ?
C00T O005 C00Y 113.0(3) . . ?
C00W O006 C011 112.8(3) . . ?
C00U O007 C010 112.4(3) . . ?
C00Z O008 C017 113.4(3) . . ?
C00V O009 C00S 113.2(3) . . ?
C015 O00A C014 112.3(3) . . ?
C012 O00B C016 111.5(3) . . ?
C019 O00C C00X 113.3(3) . . ?
C01A O00D C01C 113.0(4) . . ?
C01B O00E C018 114.2(3) . . ?
H00W N00F H00X 104(4) . . ?
H00W N00F H00Y 108(4) . . ?
H00W N00F HC 112(4) . . ?
H00X N00F H00Y 117(4) . . ?
H00X N00F HC 107(4) . . ?
H00Y N00F HC 109(4) . . ?
H00Z N00G HA 107(4) . . ?
H00Z N00G HB 113(4) . . ?
H00Z N00G HD 114(5) . . ?
HA N00G HB 113(4) . . ?
HA N00G HD 111(4) . . ?
HB N00G HD 98(4) . . ?
O003 C00P H00A 109.6 . . ?
O003 C00P H00B 109.6 . . ?
O003 C00P C00T 110.3(2) . . ?
H00A C00P H00B 108.1 . . ?
C00T C00P H00A 109.6 . . ?
C00T C00P H00B 109.6 . . ?
O004 C00Q H00C 109.8 . . ?
O004 C00Q H00D 109.8 . . ?
O004 C00Q C00R 109.5(2) . . ?
H00C C00Q H00D 108.2 . . ?
C00R C00Q H00C 109.8 . . ?
C00R C00Q H00D 109.8 . . ?
O003 C00R C00Q 109.6(2) . . ?
O003 C00R H00E 109.7 . . ?
O003 C00R H00F 109.7 . . ?
C00Q C00R H00E 109.7 . . ?
C00Q C00R H00F 109.7 . . ?
H00E C00R H00F 108.2 . . ?
O009 C00S H00G 109.9 . . ?
O009 C00S H00H 109.9 . . ?
O009 C00S C00W 109.1(2) . . ?
H00G C00S H00H 108.3 . . ?
C00W C00S H00G 109.9 . . ?
C00W C00S H00H 109.9 . . ?
O005 C00T C00P 109.6(3) . . ?
O005 C00T H00I 109.8 . . ?
O005 C00T H00J 109.8 . . ?
C00P C00T H00I 109.8 . . ?
C00P C00T H00J 109.8 . . ?
H00I C00T H00J 108.2 . . ?
O007 C00U C00X 108.6(3) . . ?
O007 C00U H00Q 110.2(17) . . ?
O007 C00U H00R 110(2) . . ?
C00X C00U H00Q 110.2(18) . . ?
C00X C00U H00R 111(2) . . ?
H00Q C00U H00R 107(3) . . ?
O009 C00V H00K 110.0 . . ?
O009 C00V H00L 110.0 . . ?
O009 C00V C00Y 108.3(3) . . ?
H00K C00V H00L 108.4 . . ?
C00Y C00V H00K 110.0 . . ?
C00Y C00V H00L 110.0 . . ?
O006 C00W C00S 110.1(2) . . ?
O006 C00W H00M 109.6 . . ?
O006 C00W H00N 109.6 . . ?
C00S C00W H00M 109.6 . . ?
C00S C00W H00N 109.6 . . ?
H00M C00W H00N 108.2 . . ?
O00C C00X C00U 109.0(3) . . ?
O00C C00X H00S 109.9 . . ?
O00C C00X H00T 109.9 . . ?
C00U C00X H00S 109.9 . . ?
C00U C00X H00T 109.9 . . ?
H00S C00X H00T 108.3 . . ?
O005 C00Y C00V 109.4(3) . . ?
O005 C00Y H00O 109.8 . . ?
O005 C00Y H00P 109.8 . . ?
C00V C00Y H00O 109.8 . . ?
C00V C00Y H00P 109.8 . . ?
H00O C00Y H00P 108.2 . . ?
O008 C00Z H00U 109.9 . . ?
O008 C00Z H00V 109.9 . . ?
O008 C00Z C01A 109.1(3) . . ?
H00U C00Z H00V 108.3 . . ?
C01A C00Z H00U 109.9 . . ?
C01A C00Z H00V 109.9 . . ?
O007 C010 H01I 109.9 . . ?
O007 C010 H01J 109.9 . . ?
O007 C010 C012 109.1(3) . . ?
H01I C010 H01J 108.3 . . ?
C012 C010 H01I 109.9 . . ?
C012 C010 H01J 109.9 . . ?
O006 C011 H01A 109.7 . . ?
O006 C011 H01B 109.7 . . ?
O006 C011 C015 110.0(3) . . ?
H01A C011 H01B 108.2 . . ?
C015 C011 H01A 109.7 . . ?
C015 C011 H01B 109.7 . . ?
O00B C012 C010 109.8(3) . . ?
O00B C012 H01K 109.7 . . ?
O00B C012 H01L 109.7 . . ?
C010 C012 H01K 109.7 . . ?
C010 C012 H01L 109.7 . . ?
H01K C012 H01L 108.2 . . ?
O004 C013 H01C 109.9 . . ?
O004 C013 H01D 109.9 . . ?
O004 C013 C014 109.0(3) . . ?
H01C C013 H01D 108.3 . . ?
C014 C013 H01C 109.9 . . ?
C014 C013 H01D 109.9 . . ?
O00A C014 C013 110.2(3) . . ?
O00A C014 H01E 109.6 . . ?
O00A C014 H01F 109.6 . . ?
C013 C014 H01E 109.6 . . ?
C013 C014 H01F 109.6 . . ?
H01E C014 H01F 108.1 . . ?
O00A C015 C011 109.4(3) . . ?
O00A C015 H01G 109(2) . . ?
O00A C015 H01H 103(2) . . ?
C011 C015 H01G 110(2) . . ?
C011 C015 H01H 112(2) . . ?
H01G C015 H01H 112(3) . . ?
O00B C016 H01M 109.6 . . ?
O00B C016 H01N 109.6 . . ?
O00B C016 C017 110.4(3) . . ?
H01M C016 H01N 108.1 . . ?
C017 C016 H01M 109.6 . . ?
C017 C016 H01N 109.6 . . ?
O008 C017 C016 109.6(3) . . ?
O008 C017 H01O 109.8 . . ?
O008 C017 H01P 109.8 . . ?
C016 C017 H01O 109.8 . . ?
C016 C017 H01P 109.8 . . ?
H01O C017 H01P 108.2 . . ?
O00E C018 H01Q 109.9 . . ?
O00E C018 H01R 109.9 . . ?
O00E C018 C019 109.0(3) . . ?
H01Q C018 H01R 108.3 . . ?
C019 C018 H01Q 109.9 . . ?
C019 C018 H01R 109.9 . . ?
O00C C019 C018 109.0(3) . . ?
O00C C019 H01S 109.9 . . ?
O00C C019 H01T 109.9 . . ?
C018 C019 H01S 109.9 . . ?
C018 C019 H01T 109.9 . . ?
H01S C019 H01T 108.3 . . ?
O00D C01A C00Z 109.9(3) . . ?
O00D C01A H01U 109.7 . . ?
O00D C01A H01V 109.7 . . ?
C00Z C01A H01U 109.7 . . ?
C00Z C01A H01V 109.7 . . ?
H01U C01A H01V 108.2 . . ?
O00E C01B H01W 109.8 . . ?
O00E C01B H01X 109.8 . . ?
O00E C01B C01C 109.3(3) . . ?
H01W C01B H01X 108.3 . . ?
C01C C01B H01W 109.8 . . ?
C01C C01B H01X 109.8 . . ?
O00D C01C C01B 110.2(3) . . ?
O00D C01C H01Y 109.6 . . ?
O00D C01C H 109.6 . . ?
C01B C01C H01Y 109.6 . . ?
C01B C01C H 109.6 . . ?
H01Y C01C H 108.1 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-01
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/MTBE'
