# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_24
_database_code_depnum_ccdc_archive 'CCDC 1552384'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2017-05-26
_audit_creation_method           CRYSTALS_ver_14.61_build_6156

_oxford_structure_analysis_title 016djd17
_chemical_name_systematic        'Compound 24'
_chemical_melting_point          'not measured'


_cell_length_a                   18.548(4)
_cell_length_b                   11.9461(13)
_cell_length_c                   18.0773(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.376(14)
_cell_angle_gamma                90
_cell_volume                     3980.7(10)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2 '
_symmetry_space_group_name_Hall  'C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y+1/2,z
-x,y,-z
-x+1/2,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            9

# Given Formula = C20 H24 Cl1 N1 O2 
# Dc =      1.30 Fooo =   1656.00 Mu =     19.97 M =    345.87
# Found Formula = C17.67 H21.28 Cl1.30 N0.89 O1.78 
# Dc =      1.20 FOOO =   1528.96 Mu =     23.56 M =    320.75

_chemical_formula_sum            'C17.67 H21.28 Cl1.30 N0.89 O1.78'
_chemical_formula_moiety         'C17.67 H21.28 Cl1.30 N0.89 O1.78'
_chemical_compound_source        .
_chemical_formula_weight         320.75


_cell_measurement_reflns_used    2350
_cell_measurement_theta_min      4
_cell_measurement_theta_max      73
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1528.965
_exptl_absorpt_coefficient_mu    2.356

# Sheldrick geometric approximatio 0.62 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.29
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            20977
_reflns_number_total             8167
_diffrn_reflns_av_R_equivalents  0.088
# Number of reflections without Friedels Law is 8167 
# Number of reflections with Friedels Law is 4356 
# Theoretical number of reflections is about 4295 


_diffrn_reflns_theta_min         4.410
_diffrn_reflns_theta_max         78.811
_diffrn_measured_fraction_theta_max 0.968

_diffrn_reflns_theta_full        74.871
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -22
_reflns_limit_h_max              22
_reflns_limit_k_min              -14
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   4.37
_oxford_diffrn_Wilson_scale      0.13

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.68
_refine_diff_density_max         1.64


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         8132
_refine_ls_number_restraints     558
_refine_ls_number_parameters     577
_oxford_refine_ls_R_factor_ref   0.1184
_refine_ls_wR_factor_ref         0.2959
_refine_ls_goodness_of_fit_ref   1.0347
_refine_ls_shift/su_max          0.0111264
_refine_ls_shift/su_mean         0.0007827


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        8133
_refine_ls_R_factor_all          0.1184
_refine_ls_wR_factor_all         0.2966

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5403
_refine_ls_R_factor_gt           0.0893
_refine_ls_wR_factor_gt          0.2241

_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_abs_structure_details 'Flack (1983), 3811 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.402E+04 0.659E+04 0.404E+04 0.167E+04 314. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.67358(13) 0.4532(2) 0.02746(13) 0.0800 1.0000 Uani . . . . . .
Cl3 Cl 0.5062(4) 0.4377(5) 0.1184(5) 0.1211 0.465(9) Uani D . P . -1 .
C4 C 0.5065(15) 0.5203(8) 0.0381(4) 0.1097 0.465(9) Uani D . P . -1 .
Cl5 Cl 0.5306(3) 0.6567(5) 0.0628(4) 0.0961 0.465(9) Uani D . P . -1 .
O6 O 0.5715(3) 0.0607(5) 0.0718(3) 0.0704 1.0000 Uani . . . . . .
C7 C 0.5430(5) -0.0407(10) 0.1023(6) 0.0841 1.0000 Uani . . . . . .
C8 C 0.6234(4) 0.0448(7) 0.0293(4) 0.0581 1.0000 Uani . . . . . .
O9 O 0.6466(3) -0.0444(5) 0.0113(3) 0.0722 1.0000 Uani . . . . . .
C10 C 0.6532(4) 0.1571(6) 0.0029(4) 0.0530 1.0000 Uani D . . . . .
N11 N 0.7344(3) 0.1552(5) 0.0089(3) 0.0496 1.0000 Uani D . . . . .
C12 C 0.7688(3) 0.2047(4) 0.0816(3) 0.0453 1.0000 Uani D . . . . .
C19 C 0.8510(4) 0.2007(6) 0.0880(4) 0.0581 1.0000 Uani . . . . . .
C20 C 0.8843(4) 0.2588(6) 0.1581(4) 0.0514 1.0000 Uani . . . . . .
C21 C 0.8713(4) 0.3708(7) 0.1703(4) 0.0599 1.0000 Uani . . . . . .
C22 C 0.9018(5) 0.4276(8) 0.2339(5) 0.0696 1.0000 Uani . . . . . .
C23 C 0.9492(5) 0.3679(8) 0.2858(4) 0.0698 1.0000 Uani . . . . . .
C24 C 0.9635(5) 0.2559(9) 0.2751(5) 0.0748 1.0000 Uani . . . . . .
C25 C 0.9299(5) 0.2021(8) 0.2116(5) 0.0678 1.0000 Uani . . . . . .
C26 C 0.7558(5) 0.2134(7) -0.0585(4) 0.0643 1.0000 Uani D . . . . .
C27 C 0.6970(5) 0.1787(8) -0.1183(5) 0.0754 1.0000 Uani . . . . . .
C28 C 0.6279(5) 0.1792(7) -0.0803(4) 0.0670 1.0000 Uani . . . . . .
O29 O 0.6018(3) 0.4970(4) 0.4439(3) 0.0590 1.0000 Uani . . . . . .
C30 C 0.5355(5) 0.4697(7) 0.3959(6) 0.0830 1.0000 Uani . . . . . .
C31 C 0.6122(4) 0.6062(6) 0.4580(3) 0.0464 1.0000 Uani . . . . . .
O32 O 0.5712(3) 0.6787(4) 0.4354(3) 0.0606 1.0000 Uani . . . . . .
C33 C 0.6794(4) 0.6215(5) 0.5113(3) 0.0499 1.0000 Uani D . . . . .
N34 N 0.7211(3) 0.7251(4) 0.4932(3) 0.0444 1.0000 Uani D . . . . .
C35 C 0.7770(4) 0.6989(5) 0.4388(3) 0.0472 1.0000 Uani D . . . . .
C36 C 0.7381(3) 0.6550(5) 0.3661(3) 0.0424 1.0000 Uani . . . . . .
C37 C 0.6865(4) 0.7181(6) 0.3224(4) 0.0517 1.0000 Uani . . . . . .
C38 C 0.6531(4) 0.6749(7) 0.2555(4) 0.0574 1.0000 Uani . . . . . .
C39 C 0.6747(5) 0.5686(7) 0.2327(4) 0.0633 1.0000 Uani . . . . . .
C40 C 0.7250(5) 0.5098(7) 0.2738(4) 0.0657 1.0000 Uani . . . . . .
C41 C 0.7577(4) 0.5511(6) 0.3419(4) 0.0510 1.0000 Uani . . . . . .
C42 C 0.8239(3) 0.8010(5) 0.4290(4) 0.0547 1.0000 Uani D . . . . .
C43 C 0.8826(5) 0.7695(10) 0.3905(5) 0.0517 0.228(7) Uani D . P 1 1 .
C44 C 0.8783(4) 0.7807(6) 0.3716(4) 0.0575 0.655(7) Uani D . P 1 2 .
C45 C 0.9353(8) 0.6940(16) 0.4234(9) 0.0513 0.228(7) Uani D . P 1 1 .
C46 C 0.9308(5) 0.6962(8) 0.3831(5) 0.0674 0.655(7) Uani D . P 1 2 .
C47 C 0.9911(8) 0.6543(18) 0.3798(12) 0.0559 0.228(7) Uani D . P 1 1 .
C48 C 0.9814(6) 0.6771(10) 0.3310(6) 0.0743 0.655(7) Uani D . P 1 2 .
C49 C 0.9818(10) 0.6842(18) 0.3100(11) 0.0559 0.228(7) Uani D . P 1 1 .
C50 C 0.9775(5) 0.7434(9) 0.2667(5) 0.0720 0.655(7) Uani D . P 1 2 .
C51 C 0.9424(10) 0.762(2) 0.2755(9) 0.0562 0.228(7) Uani D . P 1 1 .
C52 C 0.9274(6) 0.8312(8) 0.2552(4) 0.0676 0.655(7) Uani D . P 1 2 .
C53 C 0.8780(5) 0.8495(7) 0.3086(4) 0.0614 0.655(7) Uani D . P 1 2 .
C54 C 0.8853(10) 0.8049(18) 0.3163(7) 0.0522 0.228(7) Uani D . P 1 1 .
C55 C 0.7534(4) 0.7680(6) 0.5671(4) 0.0546 1.0000 Uani D . . . . .
C56 C 0.6916(5) 0.7533(6) 0.6140(4) 0.0593 1.0000 Uani . . . . . .
C57 C 0.6589(6) 0.6392(7) 0.5920(4) 0.0707 1.0000 Uani . . . . . .
C130 C 0.7399(9) 0.1423(5) 0.1461(7) 0.0469 0.559(7) Uani D . P 1 4 .
C131 C 0.7350(11) 0.1583(8) 0.1463(9) 0.0451 0.441(7) Uani D . P 1 3 .
C140 C 0.6894(8) 0.2257(9) 0.1815(7) 0.0467 0.441(7) Uani D . P 1 3 .
C141 C 0.6968(8) 0.1960(6) 0.1959(6) 0.0482 0.559(7) Uani D . P 1 4 .
C150 C 0.6614(9) 0.1874(12) 0.2451(7) 0.0624 0.441(7) Uani D . P 1 3 .
C151 C 0.6679(7) 0.1407(8) 0.2527(6) 0.0510 0.559(7) Uani D . P 1 4 .
C160 C 0.6817(8) 0.0246(8) 0.2619(6) 0.0527 0.559(7) Uani D . P 1 4 .
C161 C 0.6722(8) 0.0730(12) 0.2645(6) 0.0452 0.441(7) Uani D . P 1 3 .
C170 C 0.7253(9) -0.0328(7) 0.2151(7) 0.0529 0.559(7) Uani D . P 1 4 .
C171 C 0.7162(11) 0.0021(10) 0.2250(10) 0.0565 0.441(7) Uani D . P 1 3 .
C180 C 0.7512(11) 0.0254(7) 0.1577(8) 0.0490 0.559(7) Uani D . P 1 4 .
C181 C 0.7502(12) 0.0492(10) 0.1676(11) 0.0550 0.441(7) Uani D . P 1 3 .
H72 H 0.5336 -0.0268 0.1527 0.1260 1.0000 Uiso R . . . . .
H73 H 0.4990 -0.0609 0.0726 0.1261 1.0000 Uiso R . . . . .
H71 H 0.5777 -0.0998 0.1009 0.1259 1.0000 Uiso R . . . . .
H101 H 0.6369 0.2176 0.0338 0.0635 1.0000 Uiso R . . . . .
H121 H 0.7557 0.2841 0.0801 0.0551 0.441(7) Uiso R . P 1 3 .
H122 H 0.7535 0.2829 0.0844 0.0551 0.559(7) Uiso R . P 1 4 .
H191 H 0.8672 0.2365 0.0447 0.0690 1.0000 Uiso R . . . . .
H192 H 0.8657 0.1229 0.0895 0.0686 1.0000 Uiso R . . . . .
H211 H 0.8408 0.4102 0.1349 0.0711 1.0000 Uiso R . . . . .
H221 H 0.8915 0.5040 0.2420 0.0831 1.0000 Uiso R . . . . .
H231 H 0.9722 0.4054 0.3275 0.0840 1.0000 Uiso R . . . . .
H241 H 0.9954 0.2160 0.3093 0.0898 1.0000 Uiso R . . . . .
H251 H 0.9388 0.1262 0.2045 0.0810 1.0000 Uiso R . . . . .
H261 H 0.7567 0.2938 -0.0514 0.0769 1.0000 Uiso R . . . . .
H262 H 0.8037 0.1867 -0.0694 0.0767 1.0000 Uiso R . . . . .
H271 H 0.6938 0.2304 -0.1605 0.0908 1.0000 Uiso R . . . . .
H272 H 0.7068 0.1038 -0.1356 0.0910 1.0000 Uiso R . . . . .
H281 H 0.6041 0.2519 -0.0853 0.0799 1.0000 Uiso R . . . . .
H282 H 0.5950 0.1216 -0.1006 0.0800 1.0000 Uiso R . . . . .
H301 H 0.5314 0.3893 0.3916 0.1241 1.0000 Uiso R . . . . .
H302 H 0.4944 0.4992 0.4175 0.1240 1.0000 Uiso R . . . . .
H303 H 0.5384 0.5022 0.3473 0.1240 1.0000 Uiso R . . . . .
H331 H 0.7094 0.5554 0.5100 0.0602 1.0000 Uiso R . . . . .
H351 H 0.8097 0.6397 0.4598 0.0553 1.0000 Uiso R . . . . .
H371 H 0.6737 0.7883 0.3380 0.0610 1.0000 Uiso R . . . . .
H381 H 0.6169 0.7156 0.2269 0.0689 1.0000 Uiso R . . . . .
H391 H 0.6537 0.5394 0.1883 0.0762 1.0000 Uiso R . . . . .
H401 H 0.7387 0.4396 0.2574 0.0779 1.0000 Uiso R . . . . .
H411 H 0.7931 0.5081 0.3704 0.0611 1.0000 Uiso R . . . . .
H422 H 0.8151 0.8728 0.4458 0.0650 0.228(7) Uiso R . P 1 1 .
H421 H 0.8509 0.8194 0.4765 0.0649 0.655(7) Uiso R . P 1 2 .
H423 H 0.7927 0.8637 0.4121 0.0646 0.655(7) Uiso R . P 1 2 .
H461 H 0.9326 0.6528 0.4258 0.0809 0.655(7) Uiso R . P 1 2 .
H471 H 1.0305 0.6120 0.4001 0.0671 0.228(7) Uiso R . P 1 1 .
H491 H 1.0077 0.6411 0.2793 0.0671 0.228(7) Uiso R . P 1 1 .
H511 H 0.9510 0.7894 0.2291 0.0670 0.228(7) Uiso R . P 1 1 .
H531 H 0.8450 0.9080 0.3014 0.0731 0.655(7) Uiso R . P 1 2 .
H551 H 0.7953 0.7232 0.5852 0.0649 1.0000 Uiso R . . . . .
H552 H 0.7670 0.8460 0.5637 0.0648 1.0000 Uiso R . . . . .
H562 H 0.7092 0.7547 0.6667 0.0708 1.0000 Uiso R . . . . .
H561 H 0.6560 0.8123 0.6035 0.0710 1.0000 Uiso R . . . . .
H572 H 0.6790 0.5805 0.6252 0.0839 1.0000 Uiso R . . . . .
H571 H 0.6063 0.6402 0.5920 0.0839 1.0000 Uiso R . . . . .
H1401 H 0.6777 0.2972 0.1628 0.0560 0.441(7) Uiso R . P 1 3 .
H1411 H 0.6881 0.2722 0.1897 0.0581 0.559(7) Uiso R . P 1 4 .
H1501 H 0.6358 0.2353 0.2735 0.0741 0.441(7) Uiso R . P 1 3 .
H1511 H 0.6396 0.1785 0.2842 0.0622 0.559(7) Uiso R . P 1 4 .
H1701 H 0.7360 -0.1088 0.2222 0.0641 0.559(7) Uiso R . P 1 4 .
H1711 H 0.7221 -0.0733 0.2372 0.0662 0.441(7) Uiso R . P 1 3 .
H1801 H 0.7777 -0.0133 0.1253 0.0589 0.559(7) Uiso R . P 1 4 .
H1811 H 0.7821 0.0066 0.1430 0.0640 0.441(7) Uiso R . P 1 3 .
H111 H 0.7488(13) 0.0840(17) 0.0064(13) 0.0749 1.0000 Uiso D . . . . .
H341 H 0.6901(12) 0.7754(19) 0.4719(13) 0.0661 1.0000 Uiso D . . . . .
H483 H 1.0169 0.6225 0.3397 0.0898 0.655(7) Uiso R . P 1 2 .
H451 H 0.9341 0.6704 0.4721 0.0611 0.228(7) Uiso R . P 1 1 .
H521 H 0.9265 0.8775 0.2136 0.0821 0.655(7) Uiso R . P 1 2 .
H541 H 0.8502 0.8531 0.2937 0.0620 0.228(7) Uiso R . P 1 1 .
H501 H 1.0085 0.7281 0.2303 0.0869 0.655(7) Uiso R . P 1 2 .
H1611 H 0.6501 0.0431 0.3043 0.0541 0.441(7) Uiso R . P 1 3 .
H1601 H 0.6620 -0.0145 0.2997 0.0637 0.559(7) Uiso R . P 1 4 .
H41 H 0.5410 0.4893 0.0068 0.1320 0.465(9) Uiso R . P . -1 .
H42 H 0.4582 0.5195 0.0110 0.1321 0.465(9) Uiso R . P . -1 .
Cl2 Cl 0.15704(9) 0.4569(2) 0.45252(8) 0.0531 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.01(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl3 . C4 . 1.755(5) yes
C4 . Cl5 . 1.735(5) yes
C4 . H41 . 0.974 no
C4 . H42 . 0.972 no
O6 . C7 . 1.454(11) yes
O6 . C8 . 1.311(10) yes
C7 . H72 . 0.961 no
C7 . H73 . 0.957 no
C7 . H71 . 0.956 no
C8 . O9 . 1.207(10) yes
C8 . C10 . 1.545(9) yes
C10 . N11 . 1.499(9) yes
C10 . C28 . 1.547(9) yes
C10 . H101 . 0.982 no
N11 . C12 . 1.517(7) yes
N11 . C26 . 1.494(9) yes
N11 . H111 . 0.894(19) no
C12 . C19 . 1.516(10) yes
C12 . C131 . 1.493(6) yes
C12 . H121 . 0.979 no
C12 . C19 . 1.516(10) yes
C12 . C130 . 1.530(6) yes
C12 . H122 . 0.980 no
C19 . C20 . 1.514(9) yes
C19 . H191 . 0.969 no
C19 . H192 . 0.969 no
C20 . C21 . 1.382(10) yes
C20 . C25 . 1.388(10) yes
C21 . C22 . 1.400(10) yes
C21 . H211 . 0.933 no
C22 . C23 . 1.407(12) yes
C22 . H221 . 0.947 no
C23 . C24 . 1.381(14) yes
C23 . H231 . 0.938 no
C24 . C25 . 1.400(12) yes
C24 . H241 . 0.938 no
C25 . H251 . 0.933 no
C26 . C27 . 1.506(12) yes
C26 . H261 . 0.968 no
C26 . H262 . 0.985 no
C27 . C28 . 1.520(13) yes
C27 . H271 . 0.978 no
C27 . H272 . 0.972 no
C28 . H281 . 0.975 no
C28 . H282 . 0.966 no
O29 . C30 . 1.462(8) yes
O29 . C31 . 1.339(8) yes
C30 . H301 . 0.966 no
C30 . H302 . 0.961 no
C30 . H303 . 0.967 no
C31 . O32 . 1.195(8) yes
C31 . C33 . 1.499(9) yes
C33 . N34 . 1.513(8) yes
C33 . C57 . 1.561(10) yes
C33 . H331 . 0.968 no
N34 . C35 . 1.538(8) yes
N34 . C55 . 1.494(7) yes
N34 . H341 . 0.889(19) no
C35 . C36 . 1.520(8) yes
C35 . C42 . 1.521(9) yes
C35 . H351 . 0.981 no
C36 . C37 . 1.393(9) yes
C36 . C41 . 1.378(9) yes
C37 . C38 . 1.396(9) yes
C37 . H371 . 0.924 no
C38 . C39 . 1.407(12) yes
C38 . H381 . 0.936 no
C39 . C40 . 1.327(12) yes
C39 . H391 . 0.920 no
C40 . C41 . 1.402(9) yes
C40 . H401 . 0.934 no
C41 . H411 . 0.941 no
C42 . C43 . 1.406(6) yes
C42 . H422 . 0.930 no
C42 . C44 . 1.545(6) yes
C42 . H421 . 0.970 no
C42 . H423 . 0.974 no
C43 . C45 . 1.412(6) yes
C43 . C54 . 1.412(6) yes
C44 . C46 . 1.401(5) yes
C44 . C53 . 1.405(5) yes
C45 . C47 . 1.448(6) yes
C45 . H451 . 0.928 no
C46 . C48 . 1.421(5) yes
C46 . H461 . 0.927 no
C47 . C49 . 1.305(6) yes
C47 . H471 . 0.930 no
C48 . C50 . 1.402(5) yes
C48 . H483 . 0.928 no
C49 . C51 . 1.301(6) yes
C49 . H491 . 0.929 no
C50 . C52 . 1.401(5) yes
C50 . H501 . 0.938 no
C51 . C54 . 1.449(6) yes
C51 . H511 . 0.928 no
C52 . C53 . 1.419(5) yes
C52 . H521 . 0.933 no
C53 . H531 . 0.928 no
C54 . H541 . 0.929 no
C55 . C56 . 1.510(11) yes
C55 . H551 . 0.970 no
C55 . H552 . 0.969 no
C56 . C57 . 1.527(10) yes
C56 . H562 . 0.971 no
C56 . H561 . 0.970 no
C57 . H572 . 0.970 no
C57 . H571 . 0.976 no
C130 . C141 . 1.421(5) yes
C130 . C180 . 1.424(5) yes
C131 . C140 . 1.374(5) yes
C131 . C181 . 1.379(5) yes
C140 . C150 . 1.390(6) yes
C140 . H1401 . 0.935 no
C141 . C151 . 1.380(5) yes
C141 . H1411 . 0.929 no
C150 . C161 . 1.420(6) yes
C150 . H1501 . 0.934 no
C151 . C160 . 1.416(5) yes
C151 . H1511 . 0.933 no
C160 . C170 . 1.413(5) yes
C160 . H1601 . 0.935 no
C161 . C171 . 1.422(5) yes
C161 . H1611 . 0.938 no
C170 . C180 . 1.378(5) yes
C170 . H1701 . 0.935 no
C171 . C181 . 1.391(6) yes
C171 . H1711 . 0.930 no
C180 . H1801 . 0.930 no
C181 . H1811 . 0.931 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl3 . C4 . Cl5 . 109.88(7) yes
Cl3 . C4 . H41 . 109.2 no
Cl5 . C4 . H41 . 109.8 no
Cl3 . C4 . H42 . 108.9 no
Cl5 . C4 . H42 . 109.7 no
H41 . C4 . H42 . 109.3 no
C7 . O6 . C8 . 115.0(7) yes
O6 . C7 . H72 . 109.1 no
O6 . C7 . H73 . 108.7 no
H72 . C7 . H73 . 109.9 no
O6 . C7 . H71 . 109.4 no
H72 . C7 . H71 . 110.2 no
H73 . C7 . H71 . 109.5 no
O6 . C8 . O9 . 126.4(7) yes
O6 . C8 . C10 . 111.5(7) yes
O9 . C8 . C10 . 122.1(7) yes
C8 . C10 . N11 . 110.8(6) yes
C8 . C10 . C28 . 111.6(6) yes
N11 . C10 . C28 . 105.4(6) yes
C8 . C10 . H101 . 108.7 no
N11 . C10 . H101 . 109.9 no
C28 . C10 . H101 . 110.4 no
C10 . N11 . C12 . 112.3(5) yes
C10 . N11 . C26 . 106.8(5) yes
C12 . N11 . C26 . 113.7(5) yes
C10 . N11 . H111 . 108.3(16) no
C12 . N11 . H111 . 108.3(15) no
C26 . N11 . H111 . 107.2(16) no
N11 . C12 . C19 . 112.1(5) yes
N11 . C12 . C131 . 111.2(10) yes
C19 . C12 . C131 . 115.8(9) yes
N11 . C12 . H121 . 105.9 no
C19 . C12 . H121 . 106.0 no
C131 . C12 . H121 . 104.9 no
N11 . C12 . C19 . 112.1(5) yes
N11 . C12 . C130 . 108.7(7) yes
C19 . C12 . C130 . 111.2(8) yes
N11 . C12 . H122 . 108.6 no
C19 . C12 . H122 . 108.7 no
C130 . C12 . H122 . 107.3 no
C12 . C19 . C20 . 111.3(6) yes
C12 . C19 . H191 . 108.9 no
C20 . C19 . H191 . 109.9 no
C12 . C19 . H192 . 108.0 no
C20 . C19 . H192 . 109.2 no
H191 . C19 . H192 . 109.5 no
C19 . C20 . C21 . 121.0(6) yes
C19 . C20 . C25 . 121.3(7) yes
C21 . C20 . C25 . 117.7(7) yes
C20 . C21 . C22 . 122.6(8) yes
C20 . C21 . H211 . 118.9 no
C22 . C21 . H211 . 118.5 no
C21 . C22 . C23 . 117.9(8) yes
C21 . C22 . H221 . 121.6 no
C23 . C22 . H221 . 120.5 no
C22 . C23 . C24 . 120.9(8) yes
C22 . C23 . H231 . 119.3 no
C24 . C23 . H231 . 119.8 no
C23 . C24 . C25 . 119.0(8) yes
C23 . C24 . H241 . 121.1 no
C25 . C24 . H241 . 119.9 no
C24 . C25 . C20 . 121.9(8) yes
C24 . C25 . H251 . 119.3 no
C20 . C25 . H251 . 118.8 no
N11 . C26 . C27 . 102.7(6) yes
N11 . C26 . H261 . 110.8 no
C27 . C26 . H261 . 111.7 no
N11 . C26 . H262 . 109.7 no
C27 . C26 . H262 . 111.5 no
H261 . C26 . H262 . 110.2 no
C26 . C27 . C28 . 104.7(7) yes
C26 . C27 . H271 . 111.2 no
C28 . C27 . H271 . 111.6 no
C26 . C27 . H272 . 109.7 no
C28 . C27 . H272 . 110.3 no
H271 . C27 . H272 . 109.2 no
C10 . C28 . C27 . 105.0(7) yes
C10 . C28 . H281 . 109.3 no
C27 . C28 . H281 . 111.0 no
C10 . C28 . H282 . 111.0 no
C27 . C28 . H282 . 110.7 no
H281 . C28 . H282 . 109.8 no
C30 . O29 . C31 . 115.1(6) yes
O29 . C30 . H301 . 108.9 no
O29 . C30 . H302 . 109.2 no
H301 . C30 . H302 . 109.8 no
O29 . C30 . H303 . 108.8 no
H301 . C30 . H303 . 109.8 no
H302 . C30 . H303 . 110.4 no
O29 . C31 . O32 . 124.6(6) yes
O29 . C31 . C33 . 109.4(5) yes
O32 . C31 . C33 . 125.8(6) yes
C31 . C33 . N34 . 111.6(5) yes
C31 . C33 . C57 . 110.2(7) yes
N34 . C33 . C57 . 106.0(5) yes
C31 . C33 . H331 . 108.9 no
N34 . C33 . H331 . 110.7 no
C57 . C33 . H331 . 109.5 no
C33 . N34 . C35 . 111.7(5) yes
C33 . N34 . C55 . 104.5(5) yes
C35 . N34 . C55 . 114.2(5) yes
C33 . N34 . H341 . 109.0(16) no
C35 . N34 . H341 . 108.0(15) no
C55 . N34 . H341 . 109.3(16) no
N34 . C35 . C36 . 109.5(5) yes
N34 . C35 . C42 . 110.3(5) yes
C36 . C35 . C42 . 113.5(5) yes
N34 . C35 . H351 . 109.3 no
C36 . C35 . H351 . 107.5 no
C42 . C35 . H351 . 106.6 no
C35 . C36 . C37 . 122.2(6) yes
C35 . C36 . C41 . 117.9(6) yes
C37 . C36 . C41 . 119.8(6) yes
C36 . C37 . C38 . 120.2(6) yes
C36 . C37 . H371 . 120.1 no
C38 . C37 . H371 . 119.7 no
C37 . C38 . C39 . 118.2(7) yes
C37 . C38 . H381 . 120.5 no
C39 . C38 . H381 . 121.2 no
C38 . C39 . C40 . 121.3(6) yes
C38 . C39 . H391 . 119.3 no
C40 . C39 . H391 . 119.3 no
C39 . C40 . C41 . 120.9(7) yes
C39 . C40 . H401 . 119.8 no
C41 . C40 . H401 . 119.3 no
C40 . C41 . C36 . 119.5(7) yes
C40 . C41 . H411 . 119.8 no
C36 . C41 . H411 . 120.7 no
C35 . C42 . C43 . 109.1(7) yes
C35 . C42 . H422 . 125.3 no
C43 . C42 . H422 . 125.6 no
C35 . C42 . C44 . 112.1(5) yes
C35 . C42 . H421 . 109.0 no
C44 . C42 . H421 . 108.6 no
C35 . C42 . H423 . 109.0 no
C44 . C42 . H423 . 108.7 no
H421 . C42 . H423 . 109.5 no
C42 . C43 . C45 . 120.08(7) yes
C42 . C43 . C54 . 120.07(7) yes
C45 . C43 . C54 . 119.58(7) yes
C42 . C44 . C46 . 120.56(6) yes
C42 . C44 . C53 . 120.55(6) yes
C46 . C44 . C53 . 118.84(6) yes
C43 . C45 . C47 . 118.98(7) yes
C43 . C45 . H451 . 120.4 no
C47 . C45 . H451 . 120.7 no
C44 . C46 . C48 . 121.08(6) yes
C44 . C46 . H461 . 119.1 no
C48 . C46 . H461 . 119.8 no
C45 . C47 . C49 . 114.23(7) yes
C45 . C47 . H471 . 122.8 no
C49 . C47 . H471 . 123.0 no
C46 . C48 . C50 . 118.82(6) yes
C46 . C48 . H483 . 120.6 no
C50 . C48 . H483 . 120.6 no
C47 . C49 . C51 . 131.86(7) yes
C47 . C49 . H491 . 113.9 no
C51 . C49 . H491 . 114.2 no
C48 . C50 . C52 . 121.24(6) yes
C48 . C50 . H501 . 119.4 no
C52 . C50 . H501 . 119.3 no
C49 . C51 . C54 . 114.24(7) yes
C49 . C51 . H511 . 122.7 no
C54 . C51 . H511 . 123.1 no
C50 . C52 . C53 . 118.81(6) yes
C50 . C52 . H521 . 121.1 no
C53 . C52 . H521 . 120.1 no
C52 . C53 . C44 . 121.09(6) yes
C52 . C53 . H531 . 119.1 no
C44 . C53 . H531 . 119.8 no
C51 . C54 . C43 . 118.99(7) yes
C51 . C54 . H541 . 120.5 no
C43 . C54 . H541 . 120.5 no
N34 . C55 . C56 . 102.0(5) yes
N34 . C55 . H551 . 109.8 no
C56 . C55 . H551 . 112.1 no
N34 . C55 . H552 . 110.8 no
C56 . C55 . H552 . 111.5 no
H551 . C55 . H552 . 110.3 no
C55 . C56 . C57 . 105.2(6) yes
C55 . C56 . H562 . 110.9 no
C57 . C56 . H562 . 110.6 no
C55 . C56 . H561 . 110.4 no
C57 . C56 . H561 . 110.8 no
H562 . C56 . H561 . 109.0 no
C56 . C57 . C33 . 103.5(6) yes
C56 . C57 . H572 . 111.7 no
C33 . C57 . H572 . 111.3 no
C56 . C57 . H571 . 110.9 no
C33 . C57 . H571 . 110.4 no
H572 . C57 . H571 . 108.9 no
C12 . C130 . C141 . 122.11(7) yes
C12 . C130 . C180 . 122.12(7) yes
C141 . C130 . C180 . 115.70(6) yes
C12 . C131 . C140 . 118.61(6) yes
C12 . C131 . C181 . 118.62(6) yes
C140 . C131 . C181 . 122.77(6) yes
C131 . C140 . C150 . 119.71(7) yes
C131 . C140 . H1401 . 119.9 no
C150 . C140 . H1401 . 120.4 no
C130 . C141 . C151 . 123.21(6) yes
C130 . C141 . H1411 . 118.0 no
C151 . C141 . H1411 . 118.8 no
C140 . C150 . C161 . 117.76(7) yes
C140 . C150 . H1501 . 120.9 no
C161 . C150 . H1501 . 121.3 no
C141 . C151 . C160 . 118.45(6) yes
C141 . C151 . H1511 . 121.0 no
C160 . C151 . H1511 . 120.5 no
C151 . C160 . C170 . 120.88(6) yes
C151 . C160 . H1601 . 119.7 no
C170 . C160 . H1601 . 119.4 no
C150 . C161 . C171 . 121.51(7) yes
C150 . C161 . H1611 . 119.6 no
C171 . C161 . H1611 . 118.9 no
C160 . C170 . C180 . 118.45(6) yes
C160 . C170 . H1701 . 121.1 no
C180 . C170 . H1701 . 120.5 no
C161 . C171 . C181 . 117.76(7) yes
C161 . C171 . H1711 . 121.1 no
C181 . C171 . H1711 . 121.1 no
C130 . C180 . C170 . 123.21(6) yes
C130 . C180 . H1801 . 118.3 no
C170 . C180 . H1801 . 118.5 no
C171 . C181 . C131 . 119.71(7) yes
C171 . C181 . H1811 . 120.0 no
C131 . C181 . H1811 . 120.2 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C24 . H241 . O32 2_545 156 0.94 2.58 3.457(15) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
