# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1860930'
_audit_update_record             
;
2018-08-07 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_chemical_formula_moiety         'C33 H35 N1 O6'
# Given Formula = C33 H35 N1 O6
# Dc = 1.27 Fooo = 1152.00 Mu = 7.07 M = 541.64
# Found Formula = C33 H35 N1 O6
# Dc = 1.27 FOOO = 1152.00 Mu = 7.07 M = 541.64
_chemical_formula_sum            'C33 H35 N1 O6'
_chemical_formula_weight         541.64
# 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 .
_chemical_compound_source        ?
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'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
3 -x+1/2,y+1/2,-z+1/2
4 x+1/2,-y+1/2,z+1/2

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
#---------------------------------------------------------------
# _oxford_ data items, April 2010:
# There is some uncertainty about the correct way of forming local data
# names, e.g.
# _atom_site_special_shape_oxford
# or
# _oxford_atom_site_special_shape
# see:
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace
# A reserved prefix, e.g. foo, must be used in the following way
# " If the data file contains items defined in a DDL1 dictionary, the
# local data names assigned under the reserved prefix must contain it as
# their first component, e.g. _foo_atom_site_my_item. "
# However, this seems to say the opposite:
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html
# According to advice from the IUCr, CRYSTALS is correct
#---------------------------------------------------------------
# End of 'script/refcif.dat'
#end of refcif
_cell_length_a                   17.45405(14)
_cell_length_b                   8.11896(7)
_cell_length_c                   19.92900(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.5647(7)
_cell_angle_gamma                90
_cell_volume                     2823.06(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3015
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      2.27
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4933
# Sheldrick geometric approximatio 0.49 0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod/needle
# Non-dispersive F(000):
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26315
_diffrn_reflns_theta_full        69.485
_diffrn_reflns_theta_max         75.528
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 5681
# Theoretical number of reflections is about 11715
_diffrn_reflns_theta_min         3.321
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_limit_h_max              21
_reflns_limit_h_min              -21
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                5456
_reflns_number_total             5681
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0σ(I)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.18
_refine_ls_extinction_coef       90(30)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0210
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.0004459
_refine_ls_shift/su_mean         0.0000428
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 1.68P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1087
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1010
_refine_special_details          
;
? 
;
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# 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
O1 O 0.16952(6) 0.94558(12) 0.31668(5) 0.0269 1.0000 Uani . . . . . .
C2 C 0.18339(7) 0.84658(16) 0.36099(6) 0.0192 1.0000 Uani . . . . . .
C3 C 0.16782(7) 0.66627(16) 0.34708(6) 0.0203 1.0000 Uani . . . . . .
C4 C 0.22214(8) 0.56598(17) 0.31777(6) 0.0233 1.0000 Uani . . . . . .
C5 C 0.20387(9) 0.40470(18) 0.29958(7) 0.0295 1.0000 Uani . . . . . .
C6 C 0.13077(9) 0.34530(17) 0.30995(7) 0.0316 1.0000 Uani . . . . . .
C7 C 0.07582(9) 0.44351(18) 0.33890(7) 0.0287 1.0000 Uani . . . . . .
C8 C 0.09467(8) 0.60360(16) 0.35796(6) 0.0227 1.0000 Uani . . . . . .
O9 O 0.04529(5) 0.71098(12) 0.38713(5) 0.0284 1.0000 Uani . . . . . .
C10 C -0.02746(10) 0.6487(2) 0.40466(13) 0.0555 1.0000 Uani . . . . . .
C11 C 0.21823(7) 0.89868(15) 0.42890(6) 0.0185 1.0000 Uani . . . . . .
C12 C 0.30132(7) 0.83194(16) 0.43226(6) 0.0193 1.0000 Uani . . . . . .
C13 C 0.34241(7) 0.87027(16) 0.49922(6) 0.0193 1.0000 Uani . . . . . .
C14 C 0.41972(7) 0.78624(16) 0.50421(6) 0.0211 1.0000 Uani . . . . . .
O15 O 0.43738(6) 0.68419(12) 0.46244(5) 0.0287 1.0000 Uani . . . . . .
C16 C 0.47478(7) 0.82085(16) 0.56216(6) 0.0209 1.0000 Uani . . . . . .
C17 C 0.47419(7) 0.96086(17) 0.60435(7) 0.0232 1.0000 Uani . . . . . .
O18 O 0.42018(6) 1.07805(12) 0.59150(5) 0.0301 1.0000 Uani . . . . . .
C19 C 0.42198(9) 1.22722(19) 0.62994(8) 0.0335 1.0000 Uani . . . . . .
C20 C 0.52835(8) 0.97474(18) 0.65713(7) 0.0272 1.0000 Uani . . . . . .
C21 C 0.58254(8) 0.8522(2) 0.66808(7) 0.0295 1.0000 Uani . . . . . .
C22 C 0.58482(8) 0.71553(19) 0.62659(7) 0.0283 1.0000 Uani . . . . . .
C23 C 0.53125(7) 0.70137(17) 0.57410(6) 0.0236 1.0000 Uani . . . . . .
C24 C 0.29363(7) 0.81678(15) 0.55901(6) 0.0195 1.0000 Uani . . . . . .
C25 C 0.21048(7) 0.88165(15) 0.55346(6) 0.0183 1.0000 Uani . . . . . .
C26 C 0.17378(7) 0.82280(15) 0.48648(6) 0.0186 1.0000 Uani . . . . . .
C27 C 0.20542(8) 1.07079(16) 0.55585(6) 0.0215 1.0000 Uani . . . . . .
N28 N 0.24180(6) 1.14884(13) 0.49911(5) 0.0215 1.0000 Uani . . . . . .
C29 C 0.21317(7) 1.08708(16) 0.43421(6) 0.0212 1.0000 Uani . . . . . .
C30 C 0.23332(9) 1.32721(17) 0.50203(7) 0.0293 1.0000 Uani . . . . . .
C31 C 0.16335(7) 0.80382(16) 0.60932(6) 0.0202 1.0000 Uani . . . . . .
O32 O 0.14505(6) 0.65930(12) 0.60575(5) 0.0284 1.0000 Uani . . . . . .
C33 C 0.13484(7) 0.90504(16) 0.66694(6) 0.0206 1.0000 Uani . . . . . .
C34 C 0.18551(7) 0.96366(16) 0.71713(6) 0.0212 1.0000 Uani . . . . . .
O35 O 0.26084(5) 0.92371(12) 0.70854(5) 0.0255 1.0000 Uani . . . . . .
C36 C 0.31508(8) 0.9757(2) 0.75926(7) 0.0304 1.0000 Uani . . . . . .
C37 C 0.15817(8) 1.05171(17) 0.77141(7) 0.0250 1.0000 Uani . . . . . .
C38 C 0.07996(8) 1.08239(17) 0.77474(7) 0.0278 1.0000 Uani . . . . . .
C39 C 0.02902(8) 1.02552(18) 0.72574(7) 0.0284 1.0000 Uani . . . . . .
C40 C 0.05676(8) 0.93560(17) 0.67221(7) 0.0253 1.0000 Uani . . . . . .
H41 H 0.2713 0.6081 0.3098 0.0186 1.0000 Uiso R . . . . .
H51 H 0.2426 0.3397 0.2796 0.0272 1.0000 Uiso R . . . . .
H61 H 0.1200 0.2376 0.2968 0.0306 1.0000 Uiso R . . . . .
H71 H 0.0260 0.4027 0.3453 0.0260 1.0000 Uiso R . . . . .
H101 H -0.0548 0.7349 0.4266 0.0778 1.0000 Uiso R . . . . .
H103 H -0.0214 0.5573 0.4347 0.0782 1.0000 Uiso R . . . . .
H102 H -0.0557 0.6167 0.3647 0.0786 1.0000 Uiso R . . . . .
H122 H 0.3282 0.8854 0.3965 0.0153 1.0000 Uiso R . . . . .
H121 H 0.3001 0.7148 0.4252 0.0156 1.0000 Uiso R . . . . .
H131 H 0.3509 0.9878 0.5021 0.0150 1.0000 Uiso R . . . . .
H192 H 0.3804 1.2976 0.6138 0.0417 1.0000 Uiso R . . . . .
H193 H 0.4691 1.2811 0.6228 0.0400 1.0000 Uiso R . . . . .
H191 H 0.4167 1.2051 0.6772 0.0409 1.0000 Uiso R . . . . .
H201 H 0.5280 1.0665 0.6850 0.0232 1.0000 Uiso R . . . . .
H211 H 0.6173 0.8637 0.7037 0.0297 1.0000 Uiso R . . . . .
H221 H 0.6226 0.6343 0.6330 0.0270 1.0000 Uiso R . . . . .
H231 H 0.5335 0.6079 0.5472 0.0204 1.0000 Uiso R . . . . .
H241 H 0.3180 0.8556 0.5994 0.0155 1.0000 Uiso R . . . . .
H242 H 0.2910 0.6973 0.5593 0.0137 1.0000 Uiso R . . . . .
H261 H 0.1224 0.8642 0.4858 0.0155 1.0000 Uiso R . . . . .
H262 H 0.1746 0.7046 0.4850 0.0149 1.0000 Uiso R . . . . .
H271 H 0.2318 1.1072 0.5970 0.0191 1.0000 Uiso R . . . . .
H272 H 0.1509 1.0988 0.5565 0.0186 1.0000 Uiso R . . . . .
H291 H 0.2434 1.1359 0.3991 0.0178 1.0000 Uiso R . . . . .
H292 H 0.1591 1.1156 0.4280 0.0188 1.0000 Uiso R . . . . .
H301 H 0.2599 1.3786 0.4665 0.0353 1.0000 Uiso R . . . . .
H303 H 0.2544 1.3622 0.5438 0.0354 1.0000 Uiso R . . . . .
H302 H 0.1801 1.3595 0.4979 0.0351 1.0000 Uiso R . . . . .
H362 H 0.3651 0.9371 0.7480 0.0349 1.0000 Uiso R . . . . .
H361 H 0.3149 1.0943 0.7630 0.0350 1.0000 Uiso R . . . . .
H363 H 0.3010 0.9294 0.8005 0.0348 1.0000 Uiso R . . . . .
H371 H 0.1925 1.0914 0.8038 0.0217 1.0000 Uiso R . . . . .
H381 H 0.0641 1.1407 0.8115 0.0287 1.0000 Uiso R . . . . .
H391 H -0.0233 1.0480 0.7290 0.0263 1.0000 Uiso R . . . . .
H401 H 0.0236 0.8964 0.6382 0.0223 1.0000 Uiso R . . . . .


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
O1 . C2 . 1.2136(15) yes
C2 . C3 . 1.5131(18) yes
C2 . C11 . 1.5280(17) yes
C3 . C4 . 1.3904(18) yes
C3 . C8 . 1.3969(19) yes
C4 . C5 . 1.393(2) yes
C4 . H41 . 0.941 no
C5 . C6 . 1.385(2) yes
C5 . H51 . 0.954 no
C6 . C7 . 1.385(2) yes
C6 . H61 . 0.930 no
C7 . C8 . 1.3911(19) yes
C7 . H71 . 0.943 no
C8 . O9 . 1.3669(17) yes
O9 . C10 . 1.4191(19) yes
C10 . H101 . 0.959 no
C10 . H103 . 0.957 no
C10 . H102 . 0.961 no
C11 . C12 . 1.5479(17) yes
C11 . C26 . 1.5320(16) yes
C11 . C29 . 1.5360(17) yes
C12 . C13 . 1.5297(16) yes
C12 . H122 . 0.966 no
C12 . H121 . 0.962 no
C13 . C14 . 1.5128(17) yes
C13 . C24 . 1.5456(17) yes
C13 . H131 . 0.967 no
C14 . O15 . 1.2200(16) yes
C14 . C16 . 1.5085(17) yes
C16 . C17 . 1.4140(18) yes
C16 . C23 . 1.3987(19) yes
C17 . O18 . 1.3587(16) yes
C17 . C20 . 1.3995(18) yes
O18 . C19 . 1.4329(16) yes
C19 . H192 . 0.972 no
C19 . H193 . 0.945 no
C19 . H191 . 0.966 no
C20 . C21 . 1.386(2) yes
C20 . H201 . 0.929 no
C21 . C22 . 1.385(2) yes
C21 . H211 . 0.926 no
C22 . C23 . 1.3886(19) yes
C22 . H221 . 0.939 no
C23 . H231 . 0.931 no
C24 . C25 . 1.5450(17) yes
C24 . H241 . 0.954 no
C24 . H242 . 0.971 no
C25 . C26 . 1.5407(16) yes
C25 . C27 . 1.5390(17) yes
C25 . C31 . 1.5380(17) yes
C26 . H261 . 0.958 no
C26 . H262 . 0.960 no
C27 . N28 . 1.4570(16) yes
C27 . H271 . 0.976 no
C27 . H272 . 0.978 no
N28 . C29 . 1.4625(16) yes
N28 . C30 . 1.4571(16) yes
C29 . H291 . 0.973 no
C29 . H292 . 0.976 no
C30 . H301 . 0.954 no
C30 . H303 . 0.945 no
C30 . H302 . 0.966 no
C31 . O32 . 1.2177(16) yes
C31 . C33 . 1.5076(17) yes
C33 . C34 . 1.4003(18) yes
C33 . C40 . 1.3919(19) yes
C34 . O35 . 1.3695(16) yes
C34 . C37 . 1.3918(18) yes
O35 . C36 . 1.4295(16) yes
C36 . H362 . 0.959 no
C36 . H361 . 0.966 no
C36 . H363 . 0.942 no
C37 . C38 . 1.391(2) yes
C37 . H371 . 0.926 no
C38 . C39 . 1.382(2) yes
C38 . H381 . 0.921 no
C39 . C40 . 1.391(2) yes
C39 . H391 . 0.936 no
C40 . H401 . 0.935 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
O1 . C2 . C3 . 118.43(11) yes
O1 . C2 . C11 . 121.85(12) yes
C3 . C2 . C11 . 119.69(10) yes
C2 . C3 . C4 . 121.50(12) yes
C2 . C3 . C8 . 118.97(11) yes
C4 . C3 . C8 . 119.24(12) yes
C3 . C4 . C5 . 120.39(13) yes
C3 . C4 . H41 . 119.6 no
C5 . C4 . H41 . 120.1 no
C4 . C5 . C6 . 119.58(13) yes
C4 . C5 . H51 . 118.0 no
C6 . C5 . H51 . 122.4 no
C5 . C6 . C7 . 120.86(13) yes
C5 . C6 . H61 . 117.7 no
C7 . C6 . H61 . 121.4 no
C6 . C7 . C8 . 119.37(14) yes
C6 . C7 . H71 . 120.4 no
C8 . C7 . H71 . 120.2 no
C3 . C8 . C7 . 120.55(13) yes
C3 . C8 . O9 . 115.05(11) yes
C7 . C8 . O9 . 124.40(13) yes
C8 . O9 . C10 . 117.15(12) yes
O9 . C10 . H101 . 108.2 no
O9 . C10 . H103 . 110.3 no
O9 . C10 . H102 . 109.6 no
H101 . C10 . H103 . 109.2 no
H101 . C10 . H102 . 108.9 no
H103 . C10 . H102 . 110.6 no
C2 . C11 . C12 . 106.92(10) yes
C2 . C11 . C26 . 110.77(10) yes
C2 . C11 . C29 . 108.33(10) yes
C12 . C11 . C26 . 108.65(10) yes
C12 . C11 . C29 . 113.65(10) yes
C26 . C11 . C29 . 108.52(10) yes
C11 . C12 . C13 . 112.52(10) yes
C11 . C12 . H122 . 106.5 no
C11 . C12 . H121 . 108.8 no
C13 . C12 . H122 . 109.0 no
C13 . C12 . H121 . 109.7 no
H122 . C12 . H121 . 110.3 no
C12 . C13 . C14 . 111.21(10) yes
C12 . C13 . C24 . 111.12(10) yes
C12 . C13 . H131 . 108.7 no
C14 . C13 . C24 . 109.38(10) yes
C14 . C13 . H131 . 107.9 no
C24 . C13 . H131 . 108.5 no
C13 . C14 . O15 . 120.19(11) yes
C13 . C14 . C16 . 120.98(11) yes
O15 . C14 . C16 . 118.78(12) yes
C14 . C16 . C17 . 126.16(12) yes
C14 . C16 . C23 . 115.61(11) yes
C17 . C16 . C23 . 118.22(12) yes
C16 . C17 . O18 . 117.85(11) yes
C16 . C17 . C20 . 119.73(12) yes
O18 . C17 . C20 . 122.42(12) yes
C17 . O18 . C19 . 119.09(11) yes
O18 . C19 . H192 . 108.4 no
O18 . C19 . H193 . 108.5 no
O18 . C19 . H191 . 111.3 no
H192 . C19 . H193 . 108.9 no
H192 . C19 . H191 . 109.9 no
H193 . C19 . H191 . 109.8 no
C17 . C20 . C21 . 120.31(13) yes
C17 . C20 . H201 . 119.9 no
C21 . C20 . H201 . 119.8 no
C20 . C21 . C22 . 120.78(12) yes
C20 . C21 . H211 . 118.6 no
C22 . C21 . H211 . 120.6 no
C21 . C22 . C23 . 119.09(13) yes
C21 . C22 . H221 . 120.9 no
C23 . C22 . H221 . 120.0 no
C16 . C23 . C22 . 121.85(13) yes
C16 . C23 . H231 . 120.6 no
C22 . C23 . H231 . 117.6 no
C13 . C24 . C25 . 112.66(10) yes
C13 . C24 . H241 . 108.4 no
C13 . C24 . H242 . 108.2 no
C25 . C24 . H241 . 110.1 no
C25 . C24 . H242 . 107.2 no
H241 . C24 . H242 . 110.2 no
C24 . C25 . C26 . 108.90(10) yes
C24 . C25 . C27 . 113.11(10) yes
C24 . C25 . C31 . 109.15(10) yes
C26 . C25 . C27 . 108.27(10) yes
C26 . C25 . C31 . 106.37(10) yes
C27 . C25 . C31 . 110.81(10) yes
C11 . C26 . H261 . 110.0 no
C11 . C26 . H262 . 111.8 no
C25 . C26 . C11 . 108.49(10) yes
C25 . C26 . H261 . 105.7 no
C25 . C26 . H262 . 109.3 no
H261 . C26 . H262 . 111.4 no
C25 . C27 . N28 . 112.54(10) yes
C25 . C27 . H271 . 107.6 no
C25 . C27 . H272 . 106.8 no
N28 . C27 . H271 . 108.4 no
N28 . C27 . H272 . 110.7 no
H271 . C27 . H272 . 110.8 no
C27 . N28 . C29 . 113.06(10) yes
C27 . N28 . C30 . 110.75(10) yes
C29 . N28 . C30 . 110.09(11) yes
C11 . C29 . N28 . 112.55(10) yes
C11 . C29 . H291 . 108.8 no
C11 . C29 . H292 . 106.6 no
N28 . C29 . H291 . 108.5 no
N28 . C29 . H292 . 109.6 no
H291 . C29 . H292 . 110.7 no
N28 . C30 . H301 . 110.7 no
N28 . C30 . H303 . 107.2 no
N28 . C30 . H302 . 111.4 no
H301 . C30 . H303 . 109.8 no
H301 . C30 . H302 . 107.7 no
H303 . C30 . H302 . 110.1 no
C25 . C31 . O32 . 119.88(11) yes
C25 . C31 . C33 . 121.44(11) yes
O32 . C31 . C33 . 118.58(11) yes
C31 . C33 . C34 . 120.94(11) yes
C31 . C33 . C40 . 119.93(12) yes
C34 . C33 . C40 . 119.08(12) yes
C33 . C34 . O35 . 114.84(11) yes
C33 . C34 . C37 . 120.43(12) yes
O35 . C34 . C37 . 124.72(12) yes
C34 . O35 . C36 . 117.46(10) yes
O35 . C36 . H362 . 109.1 no
O35 . C36 . H361 . 110.2 no
O35 . C36 . H363 . 108.4 no
H362 . C36 . H361 . 110.4 no
H362 . C36 . H363 . 109.5 no
H361 . C36 . H363 . 109.2 no
C34 . C37 . C38 . 119.13(13) yes
C34 . C37 . H371 . 119.4 no
C38 . C37 . H371 . 121.4 no
C37 . C38 . C39 . 121.32(13) yes
C37 . C38 . H381 . 116.5 no
C39 . C38 . H381 . 122.2 no
C38 . C39 . C40 . 119.12(13) yes
C38 . C39 . H391 . 119.7 no
C40 . C39 . H391 . 121.1 no
C33 . C40 . C39 . 120.91(13) yes
C33 . C40 . H401 . 118.2 no
C39 . C40 . H401 . 120.9 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
C6 . H61 . O1 1_545 139.94(4) 0.930 2.551 3.3170(19) yes
C19 . H193 . O15 2_676 140.35(4) 0.945 2.405 3.1905(19) yes
C23 . H231 . O15 2_666 148.44(4) 0.931 2.434 3.2636(19) yes
C24 . H241 . O35 . 129.33(4) 0.954 2.479 3.1709(19) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 22/06/12 at 12:43:15
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 103,X'S) H   ( 102,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  19,X'S) H   ( 192,X'S) H   ( 193,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 303,X'S) H   ( 302,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 361,X'S) H   ( 363,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints 
;
#
# Punched on 22/06/12 at 12:43:15
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_oxford_diffrn_Wilson_B_factor   1.73
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_R_factor_ref   0.0389
_oxford_refine_ls_scale          9.0(3)
# The values computed from all data
_oxford_reflns_number_all        5672
# 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)
####################################################################### 
# 
# 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_mo80613a
_database_code_depnum_ccdc_archive 'CCDC 1860931'
_audit_update_record             
;
2018-08-07 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_audit_creation_date             2018-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H26 Cl3 N O3'
_chemical_formula_sum            'C30 H26 Cl3 N O3'
_chemical_formula_weight         554.87
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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                   11.083(7)
_cell_length_b                   21.629(13)
_cell_length_c                   12.241(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.92
_cell_angle_gamma                90
_cell_volume                     2616(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3015
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1526
_diffrn_reflns_av_unetI/netI     0.1431
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12653
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.883
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1977
_reflns_number_total             4056
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.867
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0998
_refine_ls_restrained_S_all      0.958
_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)+(0.1510P)²+0.0001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2507
_refine_ls_wR_factor_ref         0.2824
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1A(0.059) H1B(0.059) H3A(0.049) H3B(0.049) H5A(0.063) H5B(0.063)
 H6A(0.053) H6B(0.053) H7(0.047) H8A(0.052) H8B(0.052) H9A(0.107) H9B(0.107)
 H9C(0.107) H12(0.061) H13(0.07) H15(0.065) H16(0.056) H19(0.057) H20(0.064)
 H22(0.061) H23(0.056) H26(0.056) H27(0.061) H29(0.067) H30(0.06)
 Fixed X: H1A(0.4385) H1B(0.5538) H3A(0.386) H3B(0.3405) H5A(0.6454)
 H5B(0.497) H6A(0.6215) H6B(0.5488) H7(0.7503) H8A(0.6157) H8B(0.7212)
 H9A(0.7275) H9B(0.6853) H9C(0.5787) H12(0.1343) H13(-0.0264) H15(0.1951)
 H16(0.3536) H19(0.8441) H20(0.9833) H22(1.0969) H23(0.957) H26(0.7241)
 H27(0.8371) H29(0.5365) H30(0.4169)
 Fixed Y: H1A(0.3554) H1B(0.3101) H3A(0.2947) H3B(0.3484) H5A(0.4346)
 H5B(0.4347) H6A(0.2221) H6B(0.2119) H7(0.3011) H8A(0.2972) H8B(0.347)
 H9A(0.4451) H9B(0.3959) H9C(0.4436) H12(0.1998) H13(0.139) H15(0.1397)
 H16(0.2008) H19(0.2334) H20(0.1729) H22(0.078) H23(0.139) H26(0.4512)
 H27(0.4892) H29(0.4285) H30(0.3985)
 Fixed Z: H1A(0.6557) H1B(0.739) H3A(0.3686) H3B(0.4284) H5A(0.5509)
 H5B(0.5356) H6A(0.6476) H6B(0.5056) H7(0.6329) H8A(0.3748) H8B(0.455)
 H9A(0.7693) H9B(0.8396) H9C(0.7525) H12(0.5342) H13(0.3811) H15(0.2025)
 H16(0.3508) H19(0.7867) H20(0.9515) H22(0.7331) H23(0.5701) H26(0.4096)
 H27(0.3062) H29(-0.0091) H30(0.0918)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5166(7) 0.3324(3) 0.6619(6) 0.0489(16) Uani 1 1 d . . . . .
H1A H 0.4385 0.3554 0.6557 0.059 Uiso 1 1 calc R U . . .
H1B H 0.5538 0.3101 0.7390 0.059 Uiso 1 1 calc R U . . .
C2 C 0.4705(6) 0.2864(3) 0.5582(5) 0.0399(14) Uani 1 1 d . . . . .
C3 C 0.4165(6) 0.3229(3) 0.4375(5) 0.0407(14) Uani 1 1 d . . . . .
H3A H 0.3860 0.2947 0.3686 0.049 Uiso 1 1 calc R U . . .
H3B H 0.3405 0.3484 0.4284 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5306(6) 0.3636(3) 0.4405(6) 0.0420(14) Uani 1 1 d . . . . .
C5 C 0.5731(7) 0.4084(3) 0.5482(6) 0.0521(17) Uani 1 1 d . . . . .
H5A H 0.6454 0.4346 0.5509 0.063 Uiso 1 1 calc R U . . .
H5B H 0.4970 0.4347 0.5356 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5856(6) 0.2431(3) 0.5692(6) 0.0443(15) Uani 1 1 d . . . . .
H6A H 0.6215 0.2221 0.6476 0.053 Uiso 1 1 calc R U . . .
H6B H 0.5488 0.2119 0.5056 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7014(6) 0.2766(3) 0.5582(5) 0.0389(13) Uani 1 1 d . . . . .
H7 H 0.7503 0.3011 0.6329 0.047 Uiso 1 1 calc R U . . .
C8 C 0.6471(6) 0.3211(3) 0.4497(6) 0.0432(15) Uani 1 1 d . . . . .
H8A H 0.6157 0.2972 0.3748 0.052 Uiso 1 1 calc R U . . .
H8B H 0.7212 0.3470 0.4550 0.052 Uiso 1 1 calc R U . . .
C9 C 0.6556(9) 0.4188(4) 0.7647(7) 0.072(2) Uani 1 1 d . . . . .
H9A H 0.7275 0.4451 0.7693 0.107 Uiso 1 1 calc R U . . .
H9B H 0.6853 0.3959 0.8396 0.107 Uiso 1 1 calc R U . . .
H9C H 0.5787 0.4436 0.7525 0.107 Uiso 1 1 calc R U . . .
C10 C 0.3598(7) 0.2461(3) 0.5637(6) 0.0466(15) Uani 1 1 d . . . . .
C11 C 0.2598(6) 0.2083(3) 0.4589(6) 0.0410(14) Uani 1 1 d D . . . .
C12 C 0.1472(7) 0.1884(3) 0.4670(6) 0.0510(16) Uani 1 1 d . . . . .
H12 H 0.1343 0.1998 0.5342 0.061 Uiso 1 1 calc R U . . .
C13 C 0.0510(7) 0.1512(3) 0.3755(7) 0.0586(18) Uani 1 1 d . . . . .
H13 H -0.0264 0.1390 0.3811 0.070 Uiso 1 1 calc R U . . .
C14 C 0.0703(6) 0.1328(3) 0.2794(6) 0.0461(15) Uani 1 1 d . . . . .
C15 C 0.1827(7) 0.1518(3) 0.2696(6) 0.0539(17) Uani 1 1 d . . . . .
H15 H 0.1951 0.1397 0.2025 0.065 Uiso 1 1 calc R U . . .
C16 C 0.2770(7) 0.1886(3) 0.3580(5) 0.0463(15) Uani 1 1 d D . . . .
H16 H 0.3536 0.2008 0.3508 0.056 Uiso 1 1 calc R U . . .
C17 C 0.7984(6) 0.2307(3) 0.5509(6) 0.0431(15) Uani 1 1 d . . . . .
C18 C 0.8867(6) 0.1929(3) 0.6601(6) 0.0396(14) Uani 1 1 d . . . . .
C19 C 0.8951(7) 0.2021(3) 0.7755(6) 0.0472(16) Uani 1 1 d . . . . .
H19 H 0.8441 0.2334 0.7867 0.057 Uiso 1 1 calc R U . . .
C20 C 0.9778(7) 0.1660(3) 0.8744(6) 0.0535(17) Uani 1 1 d . . . . .
H20 H 0.9833 0.1729 0.9515 0.064 Uiso 1 1 calc R U . . .
C21 C 1.0516(6) 0.1195(3) 0.8561(6) 0.0455(15) Uani 1 1 d . . . . .
C22 C 1.0458(7) 0.1092(3) 0.7441(6) 0.0512(17) Uani 1 1 d . . . . .
H22 H 1.0969 0.0780 0.7331 0.061 Uiso 1 1 calc R U . . .
C23 C 0.9621(6) 0.1462(3) 0.6470(6) 0.0463(15) Uani 1 1 d . . . . .
H23 H 0.9570 0.1390 0.5701 0.056 Uiso 1 1 calc R U . . .
C24 C 0.4732(6) 0.4012(3) 0.3221(6) 0.0482(16) Uani 1 1 d . . . . .
C25 C 0.5587(6) 0.4209(3) 0.2629(6) 0.0430(15) Uani 1 1 d . . . . .
C26 C 0.6849(7) 0.4480(3) 0.3247(6) 0.0468(15) Uani 1 1 d . . . . .
H26 H 0.7241 0.4512 0.4096 0.056 Uiso 1 1 calc R U . . .
C27 C 0.7532(7) 0.4702(3) 0.2636(6) 0.0510(17) Uani 1 1 d . . . . .
H27 H 0.8371 0.4892 0.3062 0.061 Uiso 1 1 calc R U . . .
C28 C 0.6953(7) 0.4641(3) 0.1368(6) 0.0499(16) Uani 1 1 d . . . . .
C29 C 0.5722(8) 0.4349(3) 0.0749(6) 0.0557(18) Uani 1 1 d . . . . .
H29 H 0.5365 0.4285 -0.0091 0.067 Uiso 1 1 calc R U . . .
C30 C 0.5027(7) 0.4156(3) 0.1354(6) 0.0500(17) Uani 1 1 d . . . . .
H30 H 0.4169 0.3985 0.0918 0.060 Uiso 1 1 calc R U . . .
Cl1 Cl -0.04666(18) 0.08537(10) 0.16807(19) 0.0710(6) Uani 1 1 d . . . . .
Cl2 Cl 1.15155(19) 0.07172(8) 0.97707(16) 0.0634(6) Uani 1 1 d . . . . .
Cl3 Cl 0.7782(2) 0.49289(9) 0.05950(19) 0.0682(6) Uani 1 1 d . . . . .
N1 N 0.6186(6) 0.3765(2) 0.6639(5) 0.0482(13) Uani 1 1 d . . . . .
O1 O 0.3511(6) 0.2443(3) 0.6588(5) 0.0784(17) Uani 1 1 d . . . . .
O2 O 0.8049(6) 0.2225(2) 0.4559(5) 0.0704(16) Uani 1 1 d . . . . .
O3 O 0.3551(5) 0.4154(3) 0.2708(6) 0.0847(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.509(8) . ?
C1 N1 1.471(8) . ?
C2 C3 1.538(8) . ?
C2 C6 1.538(8) . ?
C2 C10 1.530(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.526(8) . ?
C4 C5 1.528(9) . ?
C4 C8 1.546(8) . ?
C4 C24 1.528(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 N1 1.445(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.533(8) . ?
C7 H7 0.9800 . ?
C7 C8 1.526(8) . ?
C7 C17 1.496(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 N1 1.438(8) . ?
C10 C11 1.503(9) . ?
C10 O1 1.210(8) . ?
C11 C12 1.364(9) . ?
C11 C16 1.400(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.400(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.346(9) . ?
C14 C15 1.368(9) . ?
C14 Cl1 1.730(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.494(8) . ?
C17 O2 1.211(7) . ?
C18 C19 1.387(9) . ?
C18 C23 1.366(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(9) . ?
C21 C22 1.362(9) . ?
C21 Cl2 1.733(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.493(9) . ?
C24 O3 1.207(8) . ?
C25 C26 1.383(9) . ?
C25 C30 1.399(9) . ?
C26 H26 0.9300 . ?
C26 C27 1.370(10) . ?
C27 H27 0.9300 . ?
C27 C28 1.392(9) . ?
C28 C29 1.377(10) . ?
C28 Cl3 1.708(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.354(10) . ?
C30 H30 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
H1A C1 H1B 107.6 . . ?
C2 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
N1 C1 H1A 108.8 . . ?
N1 C1 H1B 108.8 . . ?
N1 C1 C2 114.0(5) . . ?
C1 C2 C3 107.7(5) . . ?
C1 C2 C6 112.1(5) . . ?
C1 C2 C10 108.1(5) . . ?
C6 C2 C3 110.0(5) . . ?
C10 C2 C3 111.3(5) . . ?
C10 C2 C6 107.5(5) . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 C2 108.4(5) . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C3 C4 C5 108.3(5) . . ?
C3 C4 C8 108.4(5) . . ?
C3 C4 C24 107.4(5) . . ?
C5 C4 C8 113.1(5) . . ?
C5 C4 C24 108.3(5) . . ?
C24 C4 C8 111.2(5) . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C5 C4 112.2(5) . . ?
N1 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C2 C6 H6A 108.9 . . ?
C2 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C2 113.5(5) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7 107.8 . . ?
C8 C7 C6 111.0(5) . . ?
C8 C7 H7 107.8 . . ?
C17 C7 C6 110.2(5) . . ?
C17 C7 H7 107.8 . . ?
C17 C7 C8 112.2(5) . . ?
C4 C8 H8A 108.5 . . ?
C4 C8 H8B 108.5 . . ?
C7 C8 C4 115.1(5) . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
C11 C10 C2 124.7(5) . . ?
O1 C10 C2 118.4(6) . . ?
O1 C10 C11 117.0(6) . . ?
C12 C11 C10 117.1(6) . . ?
C12 C11 C16 117.6(6) . . ?
C16 C11 C10 125.2(6) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.9(6) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(7) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 119.9(7) . . ?
C13 C14 Cl1 120.3(5) . . ?
C15 C14 Cl1 119.7(5) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(7) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.9(6) . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C7 120.5(5) . . ?
O2 C17 C7 120.8(6) . . ?
O2 C17 C18 118.7(6) . . ?
C19 C18 C17 123.2(5) . . ?
C23 C18 C17 119.1(5) . . ?
C23 C18 C19 117.6(6) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.5(6) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.5(6) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 Cl2 119.6(5) . . ?
C22 C21 C20 121.5(6) . . ?
C22 C21 Cl2 118.9(5) . . ?
C21 C22 H22 120.7 . . ?
C21 C22 C23 118.5(6) . . ?
C23 C22 H22 120.7 . . ?
C18 C23 C22 122.3(6) . . ?
C18 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
C25 C24 C4 122.0(5) . . ?
O3 C24 C4 121.1(6) . . ?
O3 C24 C25 116.9(6) . . ?
C26 C25 C24 124.2(6) . . ?
C26 C25 C30 118.3(6) . . ?
C30 C25 C24 117.3(6) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 C25 121.5(6) . . ?
C27 C26 H26 119.3 . . ?
C26 C27 H27 120.5 . . ?
C26 C27 C28 119.0(6) . . ?
C28 C27 H27 120.5 . . ?
C27 C28 Cl3 119.4(5) . . ?
C29 C28 C27 119.9(7) . . ?
C29 C28 Cl3 120.7(5) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.5(6) . . ?
C30 C29 H29 119.7 . . ?
C25 C30 H30 119.7 . . ?
C29 C30 C25 120.6(6) . . ?
C29 C30 H30 119.7 . . ?
C5 N1 C1 111.6(5) . . ?
C9 N1 C1 110.1(6) . . ?
C9 N1 C5 112.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 59.6(6) . . . . ?
C1 C2 C6 C7 -64.4(7) . . . . ?
C1 C2 C10 C11 160.9(6) . . . . ?
C1 C2 C10 O1 -19.1(8) . . . . ?
C2 C1 N1 C5 54.4(7) . . . . ?
C2 C1 N1 C9 179.5(6) . . . . ?
C2 C3 C4 C5 -61.1(6) . . . . ?
C2 C3 C4 C8 62.0(6) . . . . ?
C2 C3 C4 C24 -177.8(5) . . . . ?
C2 C6 C7 C8 -46.7(7) . . . . ?
C2 C6 C7 C17 -171.5(5) . . . . ?
C2 C10 C11 C12 -163.1(6) . . . . ?
C2 C10 C11 C16 21.1(9) . . . . ?
C3 C2 C6 C7 55.6(7) . . . . ?
C3 C2 C10 C11 42.8(8) . . . . ?
C3 C2 C10 O1 -137.3(7) . . . . ?
C3 C4 C5 N1 59.1(7) . . . . ?
C3 C4 C8 C7 -56.0(7) . . . . ?
C3 C4 C24 C25 -149.2(6) . . . . ?
C3 C4 C24 O3 29.4(9) . . . . ?
C4 C5 N1 C1 -54.6(7) . . . . ?
C4 C5 N1 C9 -178.6(6) . . . . ?
C4 C24 C25 C26 -47.4(9) . . . . ?
C4 C24 C25 C30 137.4(6) . . . . ?
C5 C4 C8 C7 64.1(7) . . . . ?
C5 C4 C24 C25 94.0(7) . . . . ?
C5 C4 C24 O3 -87.5(8) . . . . ?
C6 C2 C3 C4 -63.0(6) . . . . ?
C6 C2 C10 C11 -77.8(7) . . . . ?
C6 C2 C10 O1 102.2(7) . . . . ?
C6 C7 C8 C4 47.5(7) . . . . ?
C6 C7 C17 C18 -70.0(7) . . . . ?
C6 C7 C17 O2 108.4(7) . . . . ?
C7 C17 C18 C19 -7.0(9) . . . . ?
C7 C17 C18 C23 172.1(6) . . . . ?
C8 C4 C5 N1 -61.1(7) . . . . ?
C8 C4 C24 C25 -30.8(8) . . . . ?
C8 C4 C24 O3 147.8(7) . . . . ?
C8 C7 C17 C18 165.8(5) . . . . ?
C8 C7 C17 O2 -15.8(9) . . . . ?
C10 C2 C3 C4 178.0(5) . . . . ?
C10 C2 C6 C7 176.9(5) . . . . ?
C10 C11 C12 C13 -177.8(6) . . . . ?
C10 C11 C16 C15 177.0(6) . . . . ?
C11 C12 C13 C14 1.9(11) . . . . ?
C12 C11 C16 C15 1.2(9) . . . . ?
C12 C13 C14 C15 -1.5(11) . . . . ?
C12 C13 C14 Cl1 178.5(5) . . . . ?
C13 C14 C15 C16 1.0(10) . . . . ?
C14 C15 C16 C11 -0.9(10) . . . . ?
C16 C11 C12 C13 -1.7(10) . . . . ?
C17 C7 C8 C4 171.2(5) . . . . ?
C17 C18 C19 C20 179.8(6) . . . . ?
C17 C18 C23 C22 -179.8(6) . . . . ?
C18 C19 C20 C21 -0.7(10) . . . . ?
C19 C18 C23 C22 -0.7(10) . . . . ?
C19 C20 C21 C22 0.7(10) . . . . ?
C19 C20 C21 Cl2 -177.8(5) . . . . ?
C20 C21 C22 C23 -0.7(10) . . . . ?
C21 C22 C23 C18 0.7(10) . . . . ?
C23 C18 C19 C20 0.7(10) . . . . ?
C24 C4 C5 N1 175.3(5) . . . . ?
C24 C4 C8 C7 -173.9(5) . . . . ?
C24 C25 C26 C27 -174.0(6) . . . . ?
C24 C25 C30 C29 177.2(6) . . . . ?
C25 C26 C27 C28 -1.5(10) . . . . ?
C26 C25 C30 C29 1.7(9) . . . . ?
C26 C27 C28 C29 -1.2(10) . . . . ?
C26 C27 C28 Cl3 178.8(5) . . . . ?
C27 C28 C29 C30 4.1(10) . . . . ?
C28 C29 C30 C25 -4.4(10) . . . . ?
C30 C25 C26 C27 1.2(9) . . . . ?
Cl1 C14 C15 C16 -179.0(5) . . . . ?
Cl2 C21 C22 C23 177.8(5) . . . . ?
Cl3 C28 C29 C30 -175.9(5) . . . . ?
N1 C1 C2 C3 -56.6(7) . . . . ?
N1 C1 C2 C6 64.7(7) . . . . ?
N1 C1 C2 C10 -177.0(5) . . . . ?
O1 C10 C11 C12 17.0(9) . . . . ?
O1 C10 C11 C16 -158.9(7) . . . . ?
O2 C17 C18 C19 174.6(7) . . . . ?
O2 C17 C18 C23 -6.3(9) . . . . ?
O3 C24 C25 C26 134.0(7) . . . . ?
O3 C24 C25 C30 -41.2(9) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
