# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_6797
_database_code_depnum_ccdc_archive 'CCDC 1811310'
_audit_update_record             
;
2017-12-14 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;
_audit_creation_date             2017-09-19
_audit_creation_method           CRYSTALS_ver_14.61_build_6566

_oxford_structure_analysis_title 6797
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
The difference map indicated the presence of diffuse electron
density believed to be disordered solvent. This disorder is
modelled at three partially ocupied water molecules. 
;

_cell_length_a                   13.9558(3)
_cell_length_b                   15.4622(3)
_cell_length_c                   30.6296(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6609.5(2)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2

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'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C42 H36 N1 O2 P1 
# Dc =      1.24 Fooo =   2608.00 Mu =     10.24 M =    617.73
# Found Formula = C42 H36.34 N1 O2.17 P1 
# Dc =      1.25 FOOO =   2621.60 Mu =     10.30 M =    620.79

_chemical_formula_sum            'C42 H36.34 N O2.17 P'
_chemical_formula_moiety         'C42 H36 N O2 P, 0.17(H2 O)'
_chemical_compound_source        .
_chemical_formula_weight         620.79


_cell_measurement_reflns_used    20008
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.09
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.31

_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2621.600
_exptl_absorpt_coefficient_mu    1.030

# Sheldrick geometric approximatio 0.81 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.91
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_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            51019
_reflns_number_total             13718
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0621
# Number of reflections without Friedels Law is 13718 
# Number of reflections with Friedels Law is 7572 
# Theoretical number of reflections is about 6948 

_diffrn_reflns_theta_min         3.480
_diffrn_reflns_theta_max         76.542
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        75.011
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       38
_reflns_limit_h_min              -17
_reflns_limit_h_max              17
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              38

_oxford_diffrn_Wilson_B_factor   2.19
_oxford_diffrn_Wilson_scale      0.10

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

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.24


# 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_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     888
_refine_ls_number_reflns         13717
_oxford_refine_ls_R_factor_ref   0.0359
_refine_ls_wR_factor_ref         0.0822
_refine_ls_goodness_of_fit_ref   0.9994
_refine_ls_shift/su_max          0.0008438
_refine_ls_shift/su_mean         0.0000463


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        13717
_refine_ls_R_factor_all          0.0359
_refine_ls_wR_factor_all         0.0822

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                12797
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_gt          0.0789

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661--683 
_oxford_Hooft_y                  0.002(6) # for 5968 Friedel pairs 
_oxford_Bijvoet_difference       0.001(7) # for 5968 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.000(11) # for 6146 Friedel pairs 
_refine_ls_abs_structure_Flack   0.001(7)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 5968 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    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 1.14P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
P1 P 1.0013 0.4657 0.3403 0.0214 1.0000 Uani . . . . . .
O2 O 0.9484 0.4940 0.3871 0.0216 1.0000 Uani . . . . . .
C3 C 0.8684 0.5466 0.3809 0.0212 1.0000 Uani . . . . . .
C4 C 0.8808 0.6368 0.3831 0.0263 1.0000 Uani . . . . . .
C5 C 0.8038 0.6894 0.3763 0.0292 1.0000 Uani . . . . . .
C6 C 0.7119 0.6542 0.3671 0.0261 1.0000 Uani . . . . . .
C7 C 0.6313 0.7086 0.3602 0.0352 1.0000 Uani . . . . . .
C8 C 0.5438 0.6751 0.3504 0.0400 1.0000 Uani . . . . . .
C9 C 0.5324 0.5846 0.3461 0.0379 1.0000 Uani . . . . . .
C10 C 0.6086 0.5304 0.3527 0.0289 1.0000 Uani . . . . . .
C11 C 0.7002 0.5628 0.3644 0.0229 1.0000 Uani . . . . . .
C12 C 0.7816 0.5082 0.3724 0.0208 1.0000 Uani . . . . . .
C13 C 0.7765 0.4127 0.3696 0.0205 1.0000 Uani . . . . . .
C14 C 0.7104 0.3627 0.3953 0.0215 1.0000 Uani . . . . . .
C15 C 0.6575 0.4000 0.4301 0.0259 1.0000 Uani . . . . . .
C16 C 0.5967 0.3502 0.4549 0.0321 1.0000 Uani . . . . . .
C17 C 0.5853 0.2608 0.4460 0.0337 1.0000 Uani . . . . . .
C18 C 0.6364 0.2235 0.4134 0.0301 1.0000 Uani . . . . . .
C19 C 0.7009 0.2724 0.3875 0.0246 1.0000 Uani . . . . . .
C20 C 0.7572 0.2330 0.3544 0.0280 1.0000 Uani . . . . . .
C21 C 0.8251 0.2797 0.3327 0.0277 1.0000 Uani . . . . . .
C22 C 0.8373 0.3685 0.3416 0.0220 1.0000 Uani . . . . . .
O23 O 0.9093 0.4105 0.3189 0.0242 1.0000 Uani . . . . . .
N24 N 1.0772 0.3933 0.3605 0.0241 1.0000 Uani . . . . . .
C25 C 1.1802 0.4039 0.3506 0.0260 1.0000 Uani . . . . . .
C26 C 1.0493 0.3208 0.3896 0.0279 1.0000 Uani . . . . . .
C27 C 1.0987 0.3253 0.4341 0.0336 1.0000 Uani . . . . . .
C28 C 1.0664 0.2323 0.3693 0.0412 1.0000 Uani . . . . . .
C31 C 1.1836 0.2658 0.2458 0.0546 0.9079 Uani . . P 2 1 .
C32 C 1.2734 0.2318 0.2464 0.0526 0.9079 Uani . . P 2 1 .
C33 C 1.3400 0.2571 0.2791 0.0374 0.9079 Uani . . P 2 1 .
C34 C 1.4346 0.2244 0.2793 0.0445 0.9079 Uani . . P 2 1 .
C43 C 1.2095 0.4990 0.3483 0.0280 1.0000 Uani . . . . . .
C44 C 1.2506 0.5350 0.3110 0.0342 1.0000 Uani . . . . . .
C45 C 1.2796 0.6213 0.3105 0.0389 1.0000 Uani . . . . . .
C46 C 1.2675 0.6705 0.3477 0.0388 1.0000 Uani . . . . . .
C47 C 1.2244 0.6377 0.3854 0.0361 1.0000 Uani . . . . . .
C48 C 1.1965 0.5508 0.3851 0.0316 1.0000 Uani . . . . . .
C49 C 1.3226 0.6606 0.2699 0.0544 1.0000 Uani . . . . . .
C50 C 1.2060 0.6944 0.4245 0.0523 1.0000 Uani . . . . . .
P51 P 0.7520 -0.0707 0.3967 0.0226 1.0000 Uani . . . . . .
O52 O 0.7002 0.0145 0.3732 0.0223 1.0000 Uani . . . . . .
C53 C 0.6218 -0.0087 0.3476 0.0257 1.0000 Uani . . . . . .
C54 C 0.6373 -0.0244 0.3026 0.0382 1.0000 Uani . . . . . .
C55 C 0.5616 -0.0448 0.2765 0.0492 1.0000 Uani . . . . . .
C56 C 0.4680 -0.0529 0.2942 0.0412 1.0000 Uani . . . . . .
C57 C 0.3881 -0.0729 0.2671 0.0550 1.0000 Uani . . . . . .
C58 C 0.2989 -0.0828 0.2842 0.0569 1.0000 Uani . . . . . .
C59 C 0.2852 -0.0772 0.3298 0.0461 1.0000 Uani . . . . . .
C60 C 0.3606 -0.0583 0.3568 0.0351 1.0000 Uani . . . . . .
C61 C 0.4536 -0.0419 0.3399 0.0298 1.0000 Uani . . . . . .
C62 C 0.5336 -0.0170 0.3668 0.0234 1.0000 Uani . . . . . .
C63 C 0.5255 -0.0046 0.4148 0.0215 1.0000 Uani . . . . . .
C64 C 0.4570 0.0539 0.4340 0.0241 1.0000 Uani . . . . . .
C65 C 0.4021 0.1124 0.4083 0.0299 1.0000 Uani . . . . . .
C66 C 0.3377 0.1678 0.4276 0.0389 1.0000 Uani . . . . . .
C67 C 0.3242 0.1674 0.4730 0.0442 1.0000 Uani . . . . . .
C68 C 0.3768 0.1135 0.4987 0.0401 1.0000 Uani . . . . . .
C69 C 0.4455 0.0558 0.4802 0.0298 1.0000 Uani . . . . . .
C70 C 0.5018 0.0002 0.5064 0.0339 1.0000 Uani . . . . . .
C71 C 0.5719 -0.0492 0.4881 0.0304 1.0000 Uani . . . . . .
C72 C 0.5858 -0.0490 0.4425 0.0239 1.0000 Uani . . . . . .
O73 O 0.6584 -0.1015 0.4268 0.0276 1.0000 Uani . . . . . .
N74 N 0.8266 -0.0201 0.4301 0.0236 1.0000 Uani . . . . . .
C75 C 0.9299 -0.0411 0.4264 0.0222 1.0000 Uani . . . . . .
C76 C 0.8002 0.0506 0.4607 0.0273 1.0000 Uani . . . . . .
C77 C 0.8517 0.1352 0.4503 0.0340 1.0000 Uani . . . . . .
C78 C 0.8166 0.0253 0.5082 0.0383 1.0000 Uani . . . . . .
C79 C 0.9639 -0.1100 0.4584 0.0232 1.0000 Uani . . . . . .
C80 C 0.9036 -0.1705 0.4759 0.0294 1.0000 Uani . . . . . .
C81 C 0.9356 -0.2295 0.5080 0.0355 1.0000 Uani . . . . . .
C82 C 1.0277 -0.2262 0.5228 0.0353 1.0000 Uani . . . . . .
C83 C 1.0931 -0.1660 0.5052 0.0289 1.0000 Uani . . . . . .
C84 C 1.1893 -0.1622 0.5198 0.0371 1.0000 Uani . . . . . .
C85 C 1.2519 -0.1038 0.5028 0.0399 1.0000 Uani . . . . . .
C86 C 1.2227 -0.0478 0.4692 0.0357 1.0000 Uani . . . . . .
C87 C 1.1301 -0.0500 0.4541 0.0290 1.0000 Uani . . . . . .
C88 C 1.0621 -0.1080 0.4720 0.0239 1.0000 Uani . . . . . .
C93 C 0.9594 -0.0575 0.3789 0.0232 1.0000 Uani . . . . . .
C94 C 0.9505 0.0108 0.3495 0.0322 1.0000 Uani . . . . . .
C95 C 0.9796 0.0021 0.3063 0.0369 1.0000 Uani . . . . . .
C96 C 1.0176 -0.0766 0.2928 0.0334 1.0000 Uani . . . . . .
C97 C 1.0249 -0.1466 0.3212 0.0281 1.0000 Uani . . . . . .
C98 C 0.9963 -0.1361 0.3647 0.0249 1.0000 Uani . . . . . .
C99 C 0.9698 0.0772 0.2749 0.0623 1.0000 Uani . . . . . .
C100 C 1.0630 -0.2320 0.3052 0.0408 1.0000 Uani . . . . . .
H41 H 0.9432 0.6603 0.3906 0.0322 1.0000 Uiso R . . . . .
H51 H 0.8115 0.7500 0.3778 0.0355 1.0000 Uiso R . . . . .
H71 H 0.6398 0.7701 0.3624 0.0420 1.0000 Uiso R . . . . .
H81 H 0.4905 0.7104 0.3472 0.0486 1.0000 Uiso R . . . . .
H91 H 0.4712 0.5628 0.3380 0.0442 1.0000 Uiso R . . . . .
H101 H 0.6014 0.4688 0.3489 0.0346 1.0000 Uiso R . . . . .
H151 H 0.6647 0.4579 0.4366 0.0309 1.0000 Uiso R . . . . .
H161 H 0.5632 0.3753 0.4783 0.0383 1.0000 Uiso R . . . . .
H171 H 0.5421 0.2292 0.4624 0.0406 1.0000 Uiso R . . . . .
H181 H 0.6289 0.1651 0.4079 0.0362 1.0000 Uiso R . . . . .
H201 H 0.7486 0.1743 0.3483 0.0332 1.0000 Uiso R . . . . .
H211 H 0.8633 0.2530 0.3112 0.0338 1.0000 Uiso R . . . . .
H251 H 1.2149 0.3796 0.3755 0.0304 1.0000 Uiso R . . . . .
H261 H 0.9792 0.3287 0.3947 0.0334 1.0000 Uiso R . . . . .
H271 H 1.0665 0.2866 0.4546 0.0496 1.0000 Uiso R . . . . .
H272 H 1.1666 0.3102 0.4323 0.0493 1.0000 Uiso R . . . . .
H273 H 1.0939 0.3832 0.4461 0.0499 1.0000 Uiso R . . . . .
H283 H 1.0420 0.1856 0.3888 0.0623 1.0000 Uiso R . . . . .
H282 H 1.1348 0.2220 0.3635 0.0610 1.0000 Uiso R . . . . .
H281 H 1.0349 0.2269 0.3416 0.0616 1.0000 Uiso R . . . . .
H301 H 1.0911 0.3453 0.2792 0.0500 0.9079 Uiso R . P 2 1 .
H311 H 1.1410 0.2489 0.2237 0.0661 0.9079 Uiso R . P 2 1 .
H321 H 1.2921 0.1910 0.2248 0.0632 0.9079 Uiso R . P 2 1 .
H341 H 1.4522 0.1842 0.2583 0.0536 0.9079 Uiso R . P 2 1 .
H351 H 1.5620 0.2268 0.3099 0.0510 0.9079 Uiso R . P 2 1 .
H361 H 1.5190 0.3310 0.3619 0.0367 0.9079 Uiso R . P 2 1 .
H371 H 1.3640 0.3845 0.3646 0.0293 0.9079 Uiso R . P 2 1 .
H441 H 1.2575 0.5014 0.2854 0.0410 1.0000 Uiso R . . . . .
H461 H 1.2874 0.7275 0.3478 0.0462 1.0000 Uiso R . . . . .
H481 H 1.1672 0.5268 0.4099 0.0378 1.0000 Uiso R . . . . .
H493 H 1.3402 0.7182 0.2760 0.0814 1.0000 Uiso R . . . . .
H492 H 1.3767 0.6270 0.2607 0.0823 1.0000 Uiso R . . . . .
H491 H 1.2761 0.6601 0.2475 0.0819 1.0000 Uiso R . . . . .
H501 H 1.1380 0.6969 0.4318 0.0794 1.0000 Uiso R . . . . .
H502 H 1.2397 0.6726 0.4497 0.0777 1.0000 Uiso R . . . . .
H503 H 1.2303 0.7522 0.4187 0.0778 1.0000 Uiso R . . . . .
H541 H 0.6997 -0.0162 0.2912 0.0463 1.0000 Uiso R . . . . .
H551 H 0.5701 -0.0531 0.2464 0.0595 1.0000 Uiso R . . . . .
H571 H 0.3974 -0.0773 0.2366 0.0663 1.0000 Uiso R . . . . .
H581 H 0.2458 -0.0948 0.2652 0.0683 1.0000 Uiso R . . . . .
H591 H 0.2231 -0.0854 0.3415 0.0547 1.0000 Uiso R . . . . .
H601 H 0.3514 -0.0570 0.3867 0.0425 1.0000 Uiso R . . . . .
H651 H 0.4112 0.1131 0.3780 0.0355 1.0000 Uiso R . . . . .
H661 H 0.3025 0.2063 0.4098 0.0464 1.0000 Uiso R . . . . .
H671 H 0.2784 0.2039 0.4867 0.0535 1.0000 Uiso R . . . . .
H681 H 0.3684 0.1114 0.5290 0.0472 1.0000 Uiso R . . . . .
H701 H 0.4918 -0.0024 0.5363 0.0409 1.0000 Uiso R . . . . .
H711 H 0.6122 -0.0837 0.5053 0.0364 1.0000 Uiso R . . . . .
H751 H 0.9619 0.0135 0.4347 0.0252 1.0000 Uiso R . . . . .
H761 H 0.7297 0.0608 0.4565 0.0329 1.0000 Uiso R . . . . .
H773 H 0.8210 0.1811 0.4652 0.0512 1.0000 Uiso R . . . . .
H772 H 0.9181 0.1339 0.4602 0.0506 1.0000 Uiso R . . . . .
H771 H 0.8512 0.1477 0.4196 0.0495 1.0000 Uiso R . . . . .
H781 H 0.7937 0.0708 0.5276 0.0558 1.0000 Uiso R . . . . .
H782 H 0.8840 0.0174 0.5136 0.0554 1.0000 Uiso R . . . . .
H783 H 0.7852 -0.0276 0.5163 0.0559 1.0000 Uiso R . . . . .
H801 H 0.8389 -0.1710 0.4668 0.0350 1.0000 Uiso R . . . . .
H811 H 0.8933 -0.2703 0.5195 0.0421 1.0000 Uiso R . . . . .
H821 H 1.0481 -0.2639 0.5458 0.0426 1.0000 Uiso R . . . . .
H841 H 1.2079 -0.2018 0.5419 0.0449 1.0000 Uiso R . . . . .
H851 H 1.3147 -0.1003 0.5140 0.0475 1.0000 Uiso R . . . . .
H861 H 1.2672 -0.0099 0.4566 0.0443 1.0000 Uiso R . . . . .
H871 H 1.1122 -0.0110 0.4311 0.0334 1.0000 Uiso R . . . . .
H941 H 0.9240 0.0645 0.3592 0.0387 1.0000 Uiso R . . . . .
H961 H 1.0392 -0.0846 0.2635 0.0395 1.0000 Uiso R . . . . .
H981 H 1.0013 -0.1811 0.3849 0.0299 1.0000 Uiso R . . . . .
H993 H 0.9492 0.0574 0.2466 0.0931 1.0000 Uiso R . . . . .
H992 H 1.0349 0.1016 0.2715 0.0938 1.0000 Uiso R . . . . .
H991 H 0.9249 0.1206 0.2858 0.0941 1.0000 Uiso R . . . . .
H1003 H 1.0773 -0.2741 0.3279 0.0622 1.0000 Uiso R . . . . .
H1002 H 1.1190 -0.2244 0.2878 0.0627 1.0000 Uiso R . . . . .
H1001 H 1.0169 -0.2592 0.2872 0.0637 1.0000 Uiso R . . . . .
C234 C 1.4507 0.2849 0.2688 0.0445 0.0921 Uani . . P 2 2 .
C30 C 1.1537 0.3230 0.2794 0.0405 0.9079 Uani . . P 2 1 .
C35 C 1.4995 0.2499 0.3099 0.0432 0.9079 Uani . . P 2 1 .
C235 C 1.5051 0.2880 0.3025 0.0432 0.0921 Uani . . P 2 2 .
C29 C 1.2147 0.3471 0.3123 0.0273 0.9079 Uani . . P 2 1 .
C236 C 1.4595 0.3260 0.3398 0.0318 0.0921 Uani . . P 2 2 .
C36 C 1.4732 0.3115 0.3417 0.0318 0.9079 Uani . . P 2 1 .
C37 C 1.3811 0.3432 0.3425 0.0248 0.9079 Uani . . P 2 1 .
C237 C 1.3748 0.3617 0.3465 0.0248 0.0921 Uani . . P 2 2 .
C38 C 1.3112 0.3174 0.3119 0.0268 0.9079 Uani . . P 2 1 .
H2321 H 1.3087 0.2657 0.2091 0.0631 0.0921 Uiso R . P 2 2 .
H2311 H 1.1600 0.3316 0.2090 0.0659 0.0921 Uiso R . P 2 2 .
H2341 H 1.4763 0.2629 0.2430 0.0531 0.0921 Uiso R . P 2 2 .
H2301 H 1.1003 0.3867 0.2738 0.0489 0.0921 Uiso R . P 2 2 .
H2351 H 1.5682 0.2683 0.3027 0.0519 0.0921 Uiso R . P 2 2 .
H2361 H 1.4979 0.3247 0.3647 0.0380 0.0921 Uiso R . P 2 2 .
H2371 H 1.3561 0.3911 0.3718 0.0299 0.0921 Uiso R . P 2 2 .
C229 C 1.2143 0.3739 0.3079 0.0273 0.0921 Uani . . P 2 2 .
C230 C 1.1632 0.3671 0.2730 0.0405 0.0921 Uani . . P 2 2 .
C231 C 1.1981 0.3319 0.2340 0.0546 0.0921 Uani . . P 2 2 .
C232 C 1.2891 0.2988 0.2330 0.0526 0.0921 Uani . . P 2 2 .
C233 C 1.3534 0.3123 0.2686 0.0374 0.0921 Uani . . P 2 2 .
C238 C 1.3126 0.3475 0.3057 0.0268 0.0921 Uani . . P 2 2 .
O101 O 0.1931 0.0630 0.2331 0.0769 0.1300 Uani . . . 1 1 .
H1012 H 0.1556 0.1122 0.2319 0.0941 0.1300 Uiso R . . 1 1 .
H1011 H 0.2504 0.0878 0.2442 0.0940 0.1300 Uiso R . . 1 1 .
O103 O 0.7115 0.6244 0.1935 0.1139 0.1200 Uani . . . 1 2 .
O104 O 0.8140 0.5748 0.1713 0.1388 0.0900 Uani . . . 1 3 .
H1041 H 0.8037 0.6351 0.1747 0.1295 0.0900 Uiso R . . 1 3 .
H1042 H 0.7641 0.5438 0.1855 0.1295 0.0900 Uiso R . . 1 3 .
H1031 H 0.7684 0.6575 0.1900 0.1095 0.1200 Uiso R . . 1 2 .
H1032 H 0.7279 0.5664 0.2004 0.1095 0.1200 Uiso R . . 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.209
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
P1 . O2 . 1.671 yes
P1 . O23 . 1.674 yes
P1 . N24 . 1.660 yes
O2 . C3 . 1.395 yes
C3 . C4 . 1.407 yes
C3 . C12 . 1.373 yes
C4 . C5 . 1.363 yes
C4 . H41 . 0.971 no
C5 . C6 . 1.422 yes
C5 . H51 . 0.945 no
C6 . C7 . 1.420 yes
C6 . C11 . 1.426 yes
C7 . C8 . 1.359 yes
C7 . H71 . 0.961 no
C8 . C9 . 1.415 yes
C8 . H81 . 0.928 no
C9 . C10 . 1.369 yes
C9 . H91 . 0.951 no
C10 . C11 . 1.420 yes
C10 . H101 . 0.965 no
C11 . C12 . 1.437 yes
C12 . C13 . 1.480 yes
C13 . C14 . 1.438 yes
C13 . C22 . 1.386 yes
C14 . C15 . 1.418 yes
C14 . C19 . 1.424 yes
C15 . C16 . 1.375 yes
C15 . H151 . 0.924 no
C16 . C17 . 1.417 yes
C16 . H161 . 0.940 no
C17 . C18 . 1.357 yes
C17 . H171 . 0.925 no
C18 . C19 . 1.418 yes
C18 . H181 . 0.924 no
C19 . C20 . 1.420 yes
C20 . C21 . 1.364 yes
C20 . H201 . 0.934 no
C21 . C22 . 1.411 yes
C21 . H211 . 0.943 no
C22 . O23 . 1.384 yes
N24 . C25 . 1.478 yes
N24 . C26 . 1.485 yes
C25 . C43 . 1.528 yes
C25 . H251 . 0.980 no
C25 . C29 . 1.540 yes
C25 . C43 . 1.528 yes
C25 . H251 . 0.980 no
C25 . C229 . 1.465 yes
C26 . C27 . 1.529 yes
C26 . C28 . 1.523 yes
C26 . H261 . 0.998 no
C27 . H271 . 0.976 no
C27 . H272 . 0.977 no
C27 . H273 . 0.970 no
C28 . H283 . 0.997 no
C28 . H282 . 0.984 no
C28 . H281 . 0.958 no
C31 . C32 . 1.360 yes
C31 . H311 . 0.936 no
C31 . C30 . 1.421 yes
C32 . C33 . 1.420 yes
C32 . H321 . 0.951 no
C33 . C34 . 1.414 yes
C33 . C38 . 1.429 yes
C34 . H341 . 0.926 no
C34 . C35 . 1.363 yes
C43 . C44 . 1.395 yes
C43 . C48 . 1.394 yes
C44 . C45 . 1.395 yes
C44 . H441 . 0.945 no
C45 . C46 . 1.379 yes
C45 . C49 . 1.509 yes
C46 . C47 . 1.397 yes
C46 . H461 . 0.925 no
C47 . C48 . 1.399 yes
C47 . C50 . 1.507 yes
C48 . H481 . 0.941 no
C49 . H493 . 0.943 no
C49 . H492 . 0.960 no
C49 . H491 . 0.944 no
C50 . H501 . 0.976 no
C50 . H502 . 0.963 no
C50 . H503 . 0.972 no
P51 . O52 . 1.667 yes
P51 . O73 . 1.669 yes
P51 . N74 . 1.655 yes
O52 . C53 . 1.394 yes
C53 . C54 . 1.416 yes
C53 . C62 . 1.371 yes
C54 . C55 . 1.362 yes
C54 . H541 . 0.947 no
C55 . C56 . 1.419 yes
C55 . H551 . 0.939 no
C56 . C57 . 1.424 yes
C56 . C61 . 1.424 yes
C57 . C58 . 1.360 yes
C57 . H571 . 0.947 no
C58 . C59 . 1.410 yes
C58 . H581 . 0.960 no
C59 . C60 . 1.371 yes
C59 . H591 . 0.948 no
C60 . C61 . 1.420 yes
C60 . H601 . 0.925 no
C61 . C62 . 1.439 yes
C62 . C63 . 1.486 yes
C63 . C64 . 1.440 yes
C63 . C72 . 1.378 yes
C64 . C65 . 1.422 yes
C64 . C69 . 1.425 yes
C65 . C66 . 1.375 yes
C65 . H651 . 0.938 no
C66 . C67 . 1.403 yes
C66 . H661 . 0.945 no
C67 . C68 . 1.361 yes
C67 . H671 . 0.949 no
C68 . C69 . 1.428 yes
C68 . H681 . 0.936 no
C69 . C70 . 1.416 yes
C70 . C71 . 1.362 yes
C70 . H701 . 0.926 no
C71 . C72 . 1.413 yes
C71 . H711 . 0.936 no
C72 . O73 . 1.383 yes
N74 . C75 . 1.482 yes
N74 . C76 . 1.486 yes
C75 . C79 . 1.522 yes
C75 . C93 . 1.534 yes
C75 . H751 . 0.989 no
C76 . C77 . 1.526 yes
C76 . C78 . 1.524 yes
C76 . H761 . 1.004 no
C77 . H773 . 0.945 no
C77 . H772 . 0.975 no
C77 . H771 . 0.961 no
C78 . H781 . 0.975 no
C78 . H782 . 0.963 no
C78 . H783 . 0.960 no
C79 . C80 . 1.368 yes
C79 . C88 . 1.433 yes
C80 . C81 . 1.415 yes
C80 . H801 . 0.944 no
C81 . C82 . 1.363 yes
C81 . H811 . 0.932 no
C82 . C83 . 1.411 yes
C82 . H821 . 0.958 no
C83 . C84 . 1.415 yes
C83 . C88 . 1.424 yes
C84 . C85 . 1.361 yes
C84 . H841 . 0.948 no
C85 . C86 . 1.407 yes
C85 . H851 . 0.942 no
C86 . C87 . 1.372 yes
C86 . H861 . 0.937 no
C87 . C88 . 1.417 yes
C87 . H871 . 0.959 no
C93 . C94 . 1.394 yes
C93 . C98 . 1.389 yes
C94 . C95 . 1.388 yes
C94 . H941 . 0.957 no
C95 . C96 . 1.391 yes
C95 . C99 . 1.515 yes
C96 . C97 . 1.392 yes
C96 . H961 . 0.955 no
C97 . C98 . 1.401 yes
C97 . C100 . 1.505 yes
C98 . H981 . 0.933 no
C99 . H993 . 0.961 no
C99 . H992 . 0.989 no
C99 . H991 . 0.978 no
C100 . H1003 . 0.973 no
C100 . H1002 . 0.953 no
C100 . H1001 . 0.945 no
H301 . C30 . 0.939 no
H351 . C35 . 0.944 no
H361 . C36 . 0.940 no
H371 . C37 . 0.961 no
C234 . C235 . 1.284 yes
C234 . H2341 . 0.932 no
C234 . C233 . 1.422 yes
C30 . C29 . 1.372 yes
C35 . C36 . 1.411 yes
C235 . C236 . 1.432 yes
C235 . H2351 . 0.932 no
C29 . C38 . 1.423 yes
C236 . C237 . 1.320 yes
C236 . H2361 . 0.933 no
C36 . C37 . 1.375 yes
C37 . C38 . 1.411 yes
C237 . H2371 . 0.934 no
C237 . C238 . 1.538 yes
H2321 . C232 . 0.932 no
H2311 . C231 . 0.932 no
H2301 . C230 . 0.929 no
C229 . C230 . 1.289 yes
C229 . C238 . 1.432 yes
C230 . C231 . 1.401 yes
C231 . C232 . 1.370 yes
C232 . C233 . 1.428 yes
C233 . C238 . 1.384 yes
O101 . H1012 . 0.924 no
O101 . H1011 . 0.950 no
O103 . H1031 . 0.950 no
O103 . H1032 . 0.950 no
O104 . H1041 . 0.950 no
O104 . H1042 . 0.950 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
O2 . P1 . O23 . 97.44 yes
O2 . P1 . N24 . 97.95 yes
O23 . P1 . N24 . 106.94 yes
P1 . O2 . C3 . 112.90 yes
O2 . C3 . C4 . 118.25 yes
O2 . C3 . C12 . 118.63 yes
C4 . C3 . C12 . 123.12 yes
C3 . C4 . C5 . 119.17 yes
C3 . C4 . H41 . 119.5 no
C5 . C4 . H41 . 121.3 no
C4 . C5 . C6 . 120.85 yes
C4 . C5 . H51 . 119.7 no
C6 . C5 . H51 . 119.5 no
C5 . C6 . C7 . 121.18 yes
C5 . C6 . C11 . 119.60 yes
C7 . C6 . C11 . 119.22 yes
C6 . C7 . C8 . 121.21 yes
C6 . C7 . H71 . 118.5 no
C8 . C7 . H71 . 120.3 no
C7 . C8 . C9 . 119.93 yes
C7 . C8 . H81 . 121.3 no
C9 . C8 . H81 . 118.8 no
C8 . C9 . C10 . 120.31 yes
C8 . C9 . H91 . 118.5 no
C10 . C9 . H91 . 121.2 no
C9 . C10 . C11 . 121.38 yes
C9 . C10 . H101 . 120.5 no
C11 . C10 . H101 . 118.2 no
C6 . C11 . C10 . 117.88 yes
C6 . C11 . C12 . 118.86 yes
C10 . C11 . C12 . 123.24 yes
C11 . C12 . C3 . 118.37 yes
C11 . C12 . C13 . 122.50 yes
C3 . C12 . C13 . 119.04 yes
C12 . C13 . C14 . 122.32 yes
C12 . C13 . C22 . 119.90 yes
C14 . C13 . C22 . 117.78 yes
C13 . C14 . C15 . 121.83 yes
C13 . C14 . C19 . 119.68 yes
C15 . C14 . C19 . 118.41 yes
C14 . C15 . C16 . 120.64 yes
C14 . C15 . H151 . 119.9 no
C16 . C15 . H151 . 119.4 no
C15 . C16 . C17 . 120.62 yes
C15 . C16 . H161 . 119.8 no
C17 . C16 . H161 . 119.6 no
C16 . C17 . C18 . 119.78 yes
C16 . C17 . H171 . 118.9 no
C18 . C17 . H171 . 121.3 no
C17 . C18 . C19 . 121.30 yes
C17 . C18 . H181 . 119.2 no
C19 . C18 . H181 . 119.5 no
C14 . C19 . C18 . 119.21 yes
C14 . C19 . C20 . 119.29 yes
C18 . C19 . C20 . 121.49 yes
C19 . C20 . C21 . 120.34 yes
C19 . C20 . H201 . 119.2 no
C21 . C20 . H201 . 120.5 no
C20 . C21 . C22 . 120.30 yes
C20 . C21 . H211 . 120.1 no
C22 . C21 . H211 . 119.6 no
C21 . C22 . C13 . 121.75 yes
C21 . C22 . O23 . 116.53 yes
C13 . C22 . O23 . 121.60 yes
C22 . O23 . P1 . 126.87 yes
P1 . N24 . C25 . 118.00 yes
P1 . N24 . C26 . 124.46 yes
C25 . N24 . C26 . 117.48 yes
N24 . C25 . C43 . 112.02 yes
N24 . C25 . H251 . 106.2 no
C43 . C25 . H251 . 105.8 no
N24 . C25 . C29 . 113.44 yes
C43 . C25 . C29 . 115.50 yes
H251 . C25 . C29 . 102.7 no
N24 . C25 . C43 . 112.02 yes
N24 . C25 . H251 . 106.2 no
C43 . C25 . H251 . 105.8 no
N24 . C25 . C229 . 117.70 yes
C43 . C25 . C229 . 100.19 yes
H251 . C25 . C229 . 114.4 no
N24 . C26 . C27 . 112.52 yes
N24 . C26 . C28 . 113.13 yes
C27 . C26 . C28 . 109.58 yes
N24 . C26 . H261 . 105.0 no
C27 . C26 . H261 . 107.2 no
C28 . C26 . H261 . 109.1 no
C26 . C27 . H271 . 109.8 no
C26 . C27 . H272 . 112.1 no
H271 . C27 . H272 . 109.6 no
C26 . C27 . H273 . 110.4 no
H271 . C27 . H273 . 106.9 no
H272 . C27 . H273 . 107.9 no
C26 . C28 . H283 . 110.6 no
C26 . C28 . H282 . 111.7 no
H283 . C28 . H282 . 108.7 no
C26 . C28 . H281 . 111.6 no
H283 . C28 . H281 . 108.1 no
H282 . C28 . H281 . 105.9 no
C32 . C31 . H311 . 119.2 no
C32 . C31 . C30 . 120.09 yes
H311 . C31 . C30 . 120.6 no
C31 . C32 . C33 . 120.50 yes
C31 . C32 . H321 . 120.0 no
C33 . C32 . H321 . 119.5 no
C32 . C33 . C34 . 121.05 yes
C32 . C33 . C38 . 119.41 yes
C34 . C33 . C38 . 119.54 yes
C33 . C34 . H341 . 119.0 no
C33 . C34 . C35 . 121.30 yes
H341 . C34 . C35 . 119.7 no
C25 . C43 . C44 . 122.06 yes
C25 . C43 . C48 . 118.81 yes
C44 . C43 . C48 . 119.11 yes
C43 . C44 . C45 . 120.61 yes
C43 . C44 . H441 . 120.2 no
C45 . C44 . H441 . 119.2 no
C44 . C45 . C46 . 118.95 yes
C44 . C45 . C49 . 120.56 yes
C46 . C45 . C49 . 120.48 yes
C45 . C46 . C47 . 122.30 yes
C45 . C46 . H461 . 119.4 no
C47 . C46 . H461 . 118.3 no
C46 . C47 . C48 . 117.58 yes
C46 . C47 . C50 . 121.26 yes
C48 . C47 . C50 . 121.14 yes
C47 . C48 . C43 . 121.41 yes
C47 . C48 . H481 . 119.6 no
C43 . C48 . H481 . 118.9 no
C45 . C49 . H493 . 108.7 no
C45 . C49 . H492 . 109.8 no
H493 . C49 . H492 . 111.4 no
C45 . C49 . H491 . 108.9 no
H493 . C49 . H491 . 109.3 no
H492 . C49 . H491 . 108.8 no
C47 . C50 . H501 . 111.7 no
C47 . C50 . H502 . 110.4 no
H501 . C50 . H502 . 107.8 no
C47 . C50 . H503 . 109.2 no
H501 . C50 . H503 . 110.3 no
H502 . C50 . H503 . 107.5 no
O52 . P51 . O73 . 97.18 yes
O52 . P51 . N74 . 99.55 yes
O73 . P51 . N74 . 106.59 yes
P51 . O52 . C53 . 112.29 yes
O52 . C53 . C54 . 118.13 yes
O52 . C53 . C62 . 119.23 yes
C54 . C53 . C62 . 122.63 yes
C53 . C54 . C55 . 119.48 yes
C53 . C54 . H541 . 118.5 no
C55 . C54 . H541 . 121.9 no
C54 . C55 . C56 . 120.69 yes
C54 . C55 . H551 . 120.6 no
C56 . C55 . H551 . 118.7 no
C55 . C56 . C57 . 121.13 yes
C55 . C56 . C61 . 119.64 yes
C57 . C56 . C61 . 119.23 yes
C56 . C57 . C58 . 121.14 yes
C56 . C57 . H571 . 119.0 no
C58 . C57 . H571 . 119.9 no
C57 . C58 . C59 . 119.84 yes
C57 . C58 . H581 . 119.6 no
C59 . C58 . H581 . 120.5 no
C58 . C59 . C60 . 120.49 yes
C58 . C59 . H591 . 119.4 no
C60 . C59 . H591 . 120.1 no
C59 . C60 . C61 . 121.32 yes
C59 . C60 . H601 . 119.8 no
C61 . C60 . H601 . 118.9 no
C56 . C61 . C60 . 117.73 yes
C56 . C61 . C62 . 119.02 yes
C60 . C61 . C62 . 123.24 yes
C61 . C62 . C53 . 118.40 yes
C61 . C62 . C63 . 122.78 yes
C53 . C62 . C63 . 118.74 yes
C62 . C63 . C64 . 122.26 yes
C62 . C63 . C72 . 119.80 yes
C64 . C63 . C72 . 117.92 yes
C63 . C64 . C65 . 122.17 yes
C63 . C64 . C69 . 119.47 yes
C65 . C64 . C69 . 118.32 yes
C64 . C65 . C66 . 120.77 yes
C64 . C65 . H651 . 118.7 no
C66 . C65 . H651 . 120.5 no
C65 . C66 . C67 . 120.71 yes
C65 . C66 . H661 . 118.9 no
C67 . C66 . H661 . 120.3 no
C66 . C67 . C68 . 120.24 yes
C66 . C67 . H671 . 121.6 no
C68 . C67 . H671 . 118.2 no
C67 . C68 . C69 . 120.95 yes
C67 . C68 . H681 . 121.8 no
C69 . C68 . H681 . 117.2 no
C68 . C69 . C64 . 118.95 yes
C68 . C69 . C70 . 121.74 yes
C64 . C69 . C70 . 119.30 yes
C69 . C70 . C71 . 120.40 yes
C69 . C70 . H701 . 120.2 no
C71 . C70 . H701 . 119.4 no
C70 . C71 . C72 . 120.31 yes
C70 . C71 . H711 . 121.4 no
C72 . C71 . H711 . 118.3 no
C71 . C72 . C63 . 121.75 yes
C71 . C72 . O73 . 116.22 yes
C63 . C72 . O73 . 121.82 yes
C72 . O73 . P51 . 126.67 yes
P51 . N74 . C75 . 117.45 yes
P51 . N74 . C76 . 125.56 yes
C75 . N74 . C76 . 116.74 yes
N74 . C75 . C79 . 114.07 yes
N74 . C75 . C93 . 111.65 yes
C79 . C75 . C93 . 114.21 yes
N74 . C75 . H751 . 103.5 no
C79 . C75 . H751 . 107.0 no
C93 . C75 . H751 . 105.3 no
N74 . C76 . C77 . 112.47 yes
N74 . C76 . C78 . 112.09 yes
C77 . C76 . C78 . 110.39 yes
N74 . C76 . H761 . 106.1 no
C77 . C76 . H761 . 107.5 no
C78 . C76 . H761 . 108.0 no
C76 . C77 . H773 . 109.2 no
C76 . C77 . H772 . 111.5 no
H773 . C77 . H772 . 107.3 no
C76 . C77 . H771 . 111.9 no
H773 . C77 . H771 . 108.5 no
H772 . C77 . H771 . 108.2 no
C76 . C78 . H781 . 110.3 no
C76 . C78 . H782 . 110.0 no
H781 . C78 . H782 . 107.9 no
C76 . C78 . H783 . 113.2 no
H781 . C78 . H783 . 108.0 no
H782 . C78 . H783 . 107.2 no
C75 . C79 . C80 . 122.63 yes
C75 . C79 . C88 . 118.05 yes
C80 . C79 . C88 . 119.24 yes
C79 . C80 . C81 . 121.33 yes
C79 . C80 . H801 . 118.6 no
C81 . C80 . H801 . 120.0 no
C80 . C81 . C82 . 120.28 yes
C80 . C81 . H811 . 119.9 no
C82 . C81 . H811 . 119.9 no
C81 . C82 . C83 . 120.60 yes
C81 . C82 . H821 . 120.1 no
C83 . C82 . H821 . 119.3 no
C82 . C83 . C84 . 121.38 yes
C82 . C83 . C88 . 119.38 yes
C84 . C83 . C88 . 119.24 yes
C83 . C84 . C85 . 121.03 yes
C83 . C84 . H841 . 117.3 no
C85 . C84 . H841 . 121.7 no
C84 . C85 . C86 . 120.18 yes
C84 . C85 . H851 . 119.7 no
C86 . C85 . H851 . 120.1 no
C85 . C86 . C87 . 120.32 yes
C85 . C86 . H861 . 119.5 no
C87 . C86 . H861 . 120.1 no
C86 . C87 . C88 . 121.05 yes
C86 . C87 . H871 . 118.5 no
C88 . C87 . H871 . 120.4 no
C79 . C88 . C83 . 119.07 yes
C79 . C88 . C87 . 122.79 yes
C83 . C88 . C87 . 118.14 yes
C75 . C93 . C94 . 117.69 yes
C75 . C93 . C98 . 122.76 yes
C94 . C93 . C98 . 119.53 yes
C93 . C94 . C95 . 121.09 yes
C93 . C94 . H941 . 119.4 no
C95 . C94 . H941 . 119.5 no
C94 . C95 . C96 . 118.62 yes
C94 . C95 . C99 . 120.35 yes
C96 . C95 . C99 . 121.03 yes
C95 . C96 . C97 . 121.51 yes
C95 . C96 . H961 . 120.9 no
C97 . C96 . H961 . 117.6 no
C96 . C97 . C98 . 118.87 yes
C96 . C97 . C100 . 120.29 yes
C98 . C97 . C100 . 120.85 yes
C97 . C98 . C93 . 120.34 yes
C97 . C98 . H981 . 121.4 no
C93 . C98 . H981 . 118.2 no
C95 . C99 . H993 . 110.8 no
C95 . C99 . H992 . 106.0 no
H993 . C99 . H992 . 107.7 no
C95 . C99 . H991 . 111.4 no
H993 . C99 . H991 . 109.7 no
H992 . C99 . H991 . 111.2 no
C97 . C100 . H1003 . 115.2 no
C97 . C100 . H1002 . 111.3 no
H1003 . C100 . H1002 . 108.2 no
C97 . C100 . H1001 . 109.8 no
H1003 . C100 . H1001 . 104.9 no
H1002 . C100 . H1001 . 106.8 no
C235 . C234 . H2341 . 118.0 no
C235 . C234 . C233 . 123.82 yes
H2341 . C234 . C233 . 118.1 no
C31 . C30 . H301 . 119.8 no
C31 . C30 . C29 . 121.31 yes
H301 . C30 . C29 . 118.9 no
H351 . C35 . C34 . 120.3 no
H351 . C35 . C36 . 119.8 no
C34 . C35 . C36 . 119.89 yes
C234 . C235 . C236 . 113.19 yes
C234 . C235 . H2351 . 123.4 no
C236 . C235 . H2351 . 123.4 no
C25 . C29 . C30 . 121.30 yes
C25 . C29 . C38 . 119.15 yes
C30 . C29 . C38 . 119.53 yes
C235 . C236 . C237 . 133.98 yes
C235 . C236 . H2361 . 112.7 no
C237 . C236 . H2361 . 113.3 no
C35 . C36 . H361 . 119.6 no
C35 . C36 . C37 . 119.77 yes
H361 . C36 . C37 . 120.6 no
H371 . C37 . C36 . 118.8 no
H371 . C37 . C38 . 119.0 no
C36 . C37 . C38 . 122.19 yes
C236 . C237 . H2371 . 125.7 no
C236 . C237 . C238 . 108.56 yes
H2371 . C237 . C238 . 125.8 no
C33 . C38 . C29 . 118.92 yes
C33 . C38 . C37 . 117.26 yes
C29 . C38 . C37 . 123.82 yes
C25 . C229 . C230 . 125.78 yes
C25 . C229 . C238 . 116.28 yes
C230 . C229 . C238 . 117.91 yes
H2301 . C230 . C229 . 118.5 no
H2301 . C230 . C231 . 118.4 no
C229 . C230 . C231 . 123.14 yes
C230 . C231 . H2311 . 120.3 no
C230 . C231 . C232 . 119.16 yes
H2311 . C231 . C232 . 120.6 no
H2321 . C232 . C231 . 119.7 no
H2321 . C232 . C233 . 119.6 no
C231 . C232 . C233 . 120.70 yes
C232 . C233 . C234 . 124.03 yes
C232 . C233 . C238 . 115.24 yes
C234 . C233 . C238 . 120.46 yes
C237 . C238 . C229 . 117.54 yes
C237 . C238 . C233 . 119.45 yes
C229 . C238 . C233 . 122.99 yes
H1012 . O101 . H1011 . 99.2 no
H1031 . O103 . H1032 . 109.5 no
H1041 . O104 . H1042 . 109.5 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
C44 . H441 . C230 . 122 0.95 2.49 3.094(8) yes
C70 . H701 . O2 3_456 172 0.93 2.43 3.347(8) yes
C99 . H992 . O101 1_655 138 0.99 2.57 3.376(8) yes
C232 . H2321 . C7 4_745 168 0.93 2.45 3.366(8) yes
O101 . H1012 . C31 1_455 135 0.92 2.44 3.162(8) yes
O101 . H1011 . C32 1_455 122 0.95 2.25 2.869(8) yes
O101 . H1011 . O103 4_645 131 0.95 2.06 2.779(8) yes
O104 . H1042 . C58 4_655 151 0.95 2.34 3.205(8) yes
O104 . H1042 . C59 4_655 127 0.95 2.05 2.728(8) yes
O103 . H1032 . C58 4_655 157 0.95 2.38 3.279(8) yes
O103 . H1032 . C59 4_655 140 0.95 2.41 3.199(8) yes
####################################################################### 
# 
# 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_L28-(S)-amineHCl
_database_code_depnum_ccdc_archive 'CCDC 1818575'
_audit_update_record             
;
2018-01-22 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-01-21
_audit_creation_method           CRYSTALS_ver_14.61_build_6236

_oxford_structure_analysis_title 005eaa18
_chemical_name_systematic        .
_chemical_melting_point          .

_refine_special_details          
;
On refinement, the displacement ellipsoids for the CF3 group were found to be
prolate so these were modelled using a split site model.  In order to maintain
sensible geometric and displacement parameters, same distance, thermal 
similarity and vibrational restraints were necessary.  The occupancies of the
individual components were then refined competitively in the final refinement. 
;

_cell_length_a                   11.4023(2)
_cell_length_b                   8.44600(10)
_cell_length_c                   12.1680(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.387(2)
_cell_angle_gamma                90
_cell_volume                     1040.49(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,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'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 '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'
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            2

# Given Formula = C22 H20 Cl1 F6 N1 
# Dc =      1.43 Fooo =    460.00 Mu =     21.90 M =    447.85
# Found Formula = C22 H20 Cl1 F6 N1 
# Dc =      1.43 FOOO =    460.00 Mu =     21.90 M =    447.85

_chemical_formula_sum            'C22 H20 Cl1 F6 N1'
_chemical_formula_moiety         'C22 H20 Cl1 F6 N1'
_chemical_compound_source        synthetic
_chemical_formula_weight         447.85


_cell_measurement_reflns_used    7697
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_max          0.19

_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             460.000
_exptl_absorpt_coefficient_mu    2.190

# Sheldrick geometric approximatio 0.79 0.86 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.86
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_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       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_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            11013
_reflns_number_total             4288
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0319
# Number of reflections without Friedels Law is 4288 
# Number of reflections with Friedels Law is 2312 
# Theoretical number of reflections is about 2178 


_diffrn_reflns_theta_min         4.092
_diffrn_reflns_theta_max         76.206
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        73.158
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -14
_reflns_limit_h_max              12
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   1.97
_oxford_diffrn_Wilson_scale      0.01

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

_refine_diff_density_min         -0.42
_refine_diff_density_max         0.41


# 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         4285
_refine_ls_number_restraints     565
_refine_ls_number_parameters     345
_oxford_refine_ls_R_factor_ref   0.0365
_refine_ls_wR_factor_ref         0.0950
_refine_ls_goodness_of_fit_ref   1.0028
_refine_ls_shift/su_max          0.0004348
_refine_ls_shift/su_mean         0.0000346


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4285
_refine_ls_R_factor_all          0.0365
_refine_ls_wR_factor_all         0.0950

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4200
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_gt          0.0937

_refine_ls_abs_structure_Flack   -0.007(15)
_refine_ls_abs_structure_details 'Flack (1983), 1976 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    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.54P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
N1 N 0.38369(17) 0.4135(2) 0.51718(16) 0.0183 1.0000 Uani . . . . . .
C2 C 0.3894(2) 0.3501(3) 0.6359(2) 0.0200 1.0000 Uani . . . . . .
C3 C 0.5048(2) 0.4290(3) 0.7456(2) 0.0216 1.0000 Uani . . . . . .
C4 C 0.6281(2) 0.3570(3) 0.7931(2) 0.0284 1.0000 Uani D . . . . .
C5 C 0.7361(2) 0.4250(2) 0.8929(2) 0.0341 1.0000 Uani D . . . . .
C6 C 0.7238(3) 0.5643(4) 0.9462(2) 0.0305 1.0000 Uani . . . . . .
C7 C 0.60140(18) 0.6341(3) 0.89890(19) 0.0295 1.0000 Uani D . . . . .
C8 C 0.4922(2) 0.5683(3) 0.7994(2) 0.0258 1.0000 Uani D . . . . .
C9 C 0.86495(16) 0.3386(2) 0.94636(16) 0.0545 0.769(4) Uani D . P 1 1 .
F10 F 0.9668(3) 0.4329(4) 1.0150(3) 0.0638 0.769(4) Uani D . P 1 1 .
F11 F 0.8908(2) 0.2765(4) 0.8594(2) 0.0725 0.769(4) Uani D . P 1 1 .
F12 F 0.8685(3) 0.2198(4) 1.0193(3) 0.0816 0.769(4) Uani D . P 1 1 .
C13 C 0.58292(16) 0.7841(3) 0.95504(16) 0.0438 0.769(4) Uani D . P 1 1 .
F14 F 0.6983(3) 0.8451(4) 1.0397(3) 0.0646 0.769(4) Uani D . P 1 1 .
F15 F 0.5244(3) 0.8968(3) 0.8710(2) 0.0425 0.769(4) Uani D . P 1 1 .
F16 F 0.5089(4) 0.7627(4) 1.0123(3) 0.0630 0.769(4) Uani D . P 1 1 .
C17 C 0.2571(2) 0.3645(3) 0.6367(2) 0.0208 1.0000 Uani . . . . . .
C18 C 0.1883(2) 0.5053(3) 0.6052(2) 0.0241 1.0000 Uani . . . . . .
C19 C 0.0658(2) 0.5215(3) 0.6067(2) 0.0270 1.0000 Uani . . . . . .
C20 C 0.0120(2) 0.3961(3) 0.6378(2) 0.0262 1.0000 Uani . . . . . .
C21 C 0.0781(2) 0.2489(3) 0.6702(2) 0.0225 1.0000 Uani . . . . . .
C22 C 0.0214(2) 0.1177(3) 0.7007(2) 0.0272 1.0000 Uani . . . . . .
C23 C 0.0826(3) -0.0263(3) 0.7285(2) 0.0309 1.0000 Uani . . . . . .
C24 C 0.2052(3) -0.0458(3) 0.7277(3) 0.0311 1.0000 Uani . . . . . .
C25 C 0.2632(2) 0.0789(3) 0.6998(2) 0.0274 1.0000 Uani . . . . . .
C26 C 0.2027(2) 0.2303(3) 0.6693(2) 0.0217 1.0000 Uani . . . . . .
C27 C 0.2714(2) 0.3533(3) 0.3979(2) 0.0223 1.0000 Uani . . . . . .
C28 C 0.2844(3) 0.4295(3) 0.2916(2) 0.0307 1.0000 Uani . . . . . .
C29 C 0.2724(3) 0.1744(3) 0.3912(2) 0.0301 1.0000 Uani . . . . . .
Cl30 Cl 0.36880(5) 0.78153(13) 0.49981(5) 0.0249 1.0000 Uani . . . . . .
C109 C 0.8735(4) 0.3554(4) 0.9296(3) 0.0486 0.231(4) Uani D . P 1 2 .
F110 F 0.9579(6) 0.3864(9) 1.0457(6) 0.0449 0.231(4) Uani D . P 1 2 .
F111 F 0.9276(6) 0.4130(11) 0.8595(6) 0.0597 0.231(4) Uani D . P 1 2 .
F112 F 0.8707(6) 0.1995(7) 0.9177(8) 0.0662 0.231(4) Uani D . P 1 2 .
C113 C 0.5807(3) 0.7861(5) 0.9548(3) 0.0318 0.231(4) Uani D . P 1 2 .
F114 F 0.6801(6) 0.8166(8) 1.0649(6) 0.0385 0.231(4) Uani D . P 1 2 .
F115 F 0.5682(7) 0.9122(7) 0.8844(7) 0.0328 0.231(4) Uani D . P 1 2 .
F116 F 0.4694(6) 0.7809(8) 0.9702(6) 0.0343 0.231(4) Uani D . P 1 2 .
H11 H 0.3778 0.5176 0.5161 0.0270 1.0000 Uiso R . . . . .
H12 H 0.4605 0.3914 0.5144 0.0274 1.0000 Uiso R . . . . .
H21 H 0.4116 0.2403 0.6387 0.0231 1.0000 Uiso R . . . . .
H41 H 0.6386 0.2635 0.7559 0.0335 1.0000 Uiso R . . . . .
H61 H 0.7964 0.6093 1.0127 0.0365 1.0000 Uiso R . . . . .
H81 H 0.4105 0.6170 0.7699 0.0306 1.0000 Uiso R . . . . .
H181 H 0.2231 0.5923 0.5824 0.0275 1.0000 Uiso R . . . . .
H191 H 0.0200 0.6191 0.5823 0.0303 1.0000 Uiso R . . . . .
H201 H -0.0727 0.4048 0.6360 0.0308 1.0000 Uiso R . . . . .
H221 H -0.0611 0.1309 0.6991 0.0321 1.0000 Uiso R . . . . .
H231 H 0.0433 -0.1117 0.7482 0.0362 1.0000 Uiso R . . . . .
H241 H 0.2459 -0.1459 0.7451 0.0377 1.0000 Uiso R . . . . .
H251 H 0.3464 0.0629 0.7047 0.0332 1.0000 Uiso R . . . . .
H271 H 0.1913 0.3856 0.4003 0.0267 1.0000 Uiso R . . . . .
H281 H 0.2132 0.3909 0.2151 0.0456 1.0000 Uiso R . . . . .
H282 H 0.2791 0.5438 0.2942 0.0453 1.0000 Uiso R . . . . .
H283 H 0.3677 0.4004 0.2949 0.0448 1.0000 Uiso R . . . . .
H291 H 0.2018 0.1425 0.3119 0.0446 1.0000 Uiso R . . . . .
H292 H 0.2607 0.1229 0.4556 0.0451 1.0000 Uiso R . . . . .
H293 H 0.3550 0.1409 0.3962 0.0444 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          10.3(4)
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
N1 . C2 . 1.513(3) yes
N1 . C27 . 1.515(3) yes
N1 . H11 . 0.881 no
N1 . H12 . 0.911 no
C2 . C3 . 1.530(3) yes
C2 . C17 . 1.519(3) yes
C2 . H21 . 0.957 no
C3 . C4 . 1.390(3) yes
C3 . C8 . 1.386(3) yes
C4 . C5 . 1.395(3) yes
C4 . H41 . 0.944 no
C5 . C6 . 1.381(3) yes
C5 . C9 . 1.496(3) yes
C5 . C6 . 1.381(3) yes
C5 . C109 . 1.535(4) yes
C6 . C7 . 1.374(3) yes
C6 . H61 . 0.932 no
C7 . C8 . 1.392(3) yes
C7 . C13 . 1.499(3) yes
C7 . C8 . 1.392(3) yes
C7 . C113 . 1.521(5) yes
C8 . H81 . 0.927 no
C9 . F10 . 1.337(3) yes
C9 . F11 . 1.330(3) yes
C9 . F12 . 1.328(4) yes
C13 . F14 . 1.345(3) yes
C13 . F15 . 1.330(3) yes
C13 . F16 . 1.331(3) yes
C17 . C18 . 1.378(3) yes
C17 . C26 . 1.433(3) yes
C18 . C19 . 1.413(3) yes
C18 . H181 . 0.935 no
C19 . C20 . 1.362(4) yes
C19 . H191 . 0.947 no
C20 . C21 . 1.413(3) yes
C20 . H201 . 0.959 no
C21 . C22 . 1.416(3) yes
C21 . C26 . 1.434(3) yes
C22 . C23 . 1.365(4) yes
C22 . H221 . 0.938 no
C23 . C24 . 1.412(4) yes
C23 . H231 . 0.937 no
C24 . C25 . 1.366(3) yes
C24 . H241 . 0.941 no
C25 . C26 . 1.419(3) yes
C25 . H251 . 0.934 no
C27 . C28 . 1.513(3) yes
C27 . C29 . 1.513(3) yes
C27 . H271 . 0.967 no
C28 . H281 . 0.968 no
C28 . H282 . 0.969 no
C28 . H283 . 0.963 no
C29 . H291 . 0.968 no
C29 . H292 . 0.958 no
C29 . H293 . 0.958 no
C109 . F110 . 1.319(6) yes
C109 . F111 . 1.353(6) yes
C109 . F112 . 1.324(6) yes
C113 . F114 . 1.322(6) yes
C113 . F115 . 1.333(6) yes
C113 . F116 . 1.367(6) yes
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
C2 . N1 . C27 . 116.23(17) yes
C2 . N1 . H11 . 109.7 no
C27 . N1 . H11 . 107.2 no
C2 . N1 . H12 . 110.1 no
C27 . N1 . H12 . 107.4 no
H11 . N1 . H12 . 105.7 no
N1 . C2 . C3 . 108.72(17) yes
N1 . C2 . C17 . 111.78(17) yes
C3 . C2 . C17 . 114.71(19) yes
N1 . C2 . H21 . 105.7 no
C3 . C2 . H21 . 106.5 no
C17 . C2 . H21 . 108.9 no
C2 . C3 . C4 . 118.1(2) yes
C2 . C3 . C8 . 123.2(2) yes
C4 . C3 . C8 . 118.7(2) yes
C3 . C4 . C5 . 120.02(17) yes
C3 . C4 . H41 . 119.6 no
C5 . C4 . H41 . 120.4 no
C4 . C5 . C6 . 121.38(17) yes
C4 . C5 . C9 . 118.35(6) yes
C6 . C5 . C9 . 120.18(16) yes
C4 . C5 . C6 . 121.38(17) yes
C4 . C5 . C109 . 118.00(6) yes
C6 . C5 . C109 . 119.97(18) yes
C5 . C6 . C7 . 118.1(2) yes
C5 . C6 . H61 . 120.9 no
C7 . C6 . H61 . 121.0 no
C6 . C7 . C8 . 121.51(17) yes
C6 . C7 . C13 . 120.01(17) yes
C8 . C7 . C13 . 118.47(6) yes
C6 . C7 . C8 . 121.51(17) yes
C6 . C7 . C113 . 120.74(18) yes
C8 . C7 . C113 . 117.75(6) yes
C7 . C8 . C3 . 120.28(16) yes
C7 . C8 . H81 . 119.9 no
C3 . C8 . H81 . 119.9 no
C5 . C9 . F10 . 112.23(6) yes
C5 . C9 . F11 . 112.31(6) yes
F10 . C9 . F11 . 106.56(6) yes
C5 . C9 . F12 . 112.41(6) yes
F10 . C9 . F12 . 106.40(6) yes
F11 . C9 . F12 . 106.49(6) yes
C7 . C13 . F14 . 112.31(6) yes
C7 . C13 . F15 . 112.32(6) yes
F14 . C13 . F15 . 106.44(6) yes
C7 . C13 . F16 . 112.30(6) yes
F14 . C13 . F16 . 106.43(6) yes
F15 . C13 . F16 . 106.60(6) yes
C2 . C17 . C18 . 120.4(2) yes
C2 . C17 . C26 . 119.8(2) yes
C18 . C17 . C26 . 119.8(2) yes
C17 . C18 . C19 . 121.3(2) yes
C17 . C18 . H181 . 119.7 no
C19 . C18 . H181 . 119.0 no
C18 . C19 . C20 . 120.2(2) yes
C18 . C19 . H191 . 119.1 no
C20 . C19 . H191 . 120.7 no
C19 . C20 . C21 . 120.8(2) yes
C19 . C20 . H201 . 120.8 no
C21 . C20 . H201 . 118.5 no
C20 . C21 . C22 . 120.8(2) yes
C20 . C21 . C26 . 119.8(2) yes
C22 . C21 . C26 . 119.3(2) yes
C21 . C22 . C23 . 121.2(2) yes
C21 . C22 . H221 . 118.5 no
C23 . C22 . H221 . 120.2 no
C22 . C23 . C24 . 119.8(2) yes
C22 . C23 . H231 . 119.9 no
C24 . C23 . H231 . 120.2 no
C23 . C24 . C25 . 120.4(2) yes
C23 . C24 . H241 . 119.4 no
C25 . C24 . H241 . 120.3 no
C24 . C25 . C26 . 121.8(2) yes
C24 . C25 . H251 . 117.8 no
C26 . C25 . H251 . 120.3 no
C21 . C26 . C17 . 118.1(2) yes
C21 . C26 . C25 . 117.4(2) yes
C17 . C26 . C25 . 124.4(2) yes
N1 . C27 . C28 . 107.71(19) yes
N1 . C27 . C29 . 111.3(2) yes
C28 . C27 . C29 . 111.9(2) yes
N1 . C27 . H271 . 105.7 no
C28 . C27 . H271 . 111.8 no
C29 . C27 . H271 . 108.3 no
C27 . C28 . H281 . 108.1 no
C27 . C28 . H282 . 111.3 no
H281 . C28 . H282 . 109.3 no
C27 . C28 . H283 . 109.8 no
H281 . C28 . H283 . 109.2 no
H282 . C28 . H283 . 109.2 no
C27 . C29 . H291 . 108.0 no
C27 . C29 . H292 . 113.7 no
H291 . C29 . H292 . 108.9 no
C27 . C29 . H293 . 108.8 no
H291 . C29 . H293 . 108.8 no
H292 . C29 . H293 . 108.5 no
C5 . C109 . F110 . 112.35(6) yes
C5 . C109 . F111 . 112.35(6) yes
F110 . C109 . F111 . 106.49(6) yes
C5 . C109 . F112 . 112.29(6) yes
F110 . C109 . F112 . 106.47(6) yes
F111 . C109 . F112 . 106.45(6) yes
C7 . C113 . F114 . 112.40(6) yes
C7 . C113 . F115 . 112.30(6) yes
F114 . C113 . F115 . 106.52(6) yes
C7 . C113 . F116 . 112.26(6) yes
F114 . C113 . F116 . 106.52(6) yes
F115 . C113 . F116 . 106.40(6) yes
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
C8 . H81 . C18 . 126 0.93 2.58 3.215(4) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-5 8 9 x .
3 0 3 x .
0 -10 3 x .


####################################################################### 
# 
# 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_L26-(S)-amineHCl
_database_code_depnum_ccdc_archive 'CCDC 1818574'
_audit_update_record             
;
2018-01-22 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-01-21
_audit_creation_method           CRYSTALS_ver_14.61_build_6236

_oxford_structure_analysis_title 006eaa18
_chemical_name_systematic        .
_chemical_melting_point          .

_refine_special_details          
;
On refinement, the displacement ellipsoids for the diethylbenzene group were
found to be prolate so these were modelled using a split site model. In order
to maintain sensible geometric and displacement parameters, same distance, 
thermal similarity and vibrational restraints were necessary.  The occupancies
of the individual components were then refined competitively in the final
refinement. 
;

_cell_length_a                   8.33200(10)
_cell_length_b                   11.3877(2)
_cell_length_c                   22.1875(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2105.20(6)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2

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'
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            4

# Given Formula = C24 H30 Cl1 N1 
# Dc =      1.16 Fooo =    792.00 Mu =     16.32 M =    367.96
# Found Formula = C24 H30 Cl1 N1 
# Dc =      1.16 FOOO =    791.99 Mu =     16.32 M =    367.96

_chemical_formula_sum            'C24 H30 Cl1 N1'
_chemical_formula_moiety         'C24 H30 Cl1 N1'
_chemical_compound_source        synthetic
_chemical_formula_weight         367.96


_cell_measurement_reflns_used    8206
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_max          0.21

_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             791.995
_exptl_absorpt_coefficient_mu    1.632

# Sheldrick geometric approximatio 0.84 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_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       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_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            16356
_reflns_number_total             4373
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0532
# Number of reflections without Friedels Law is 4373 
# Number of reflections with Friedels Law is 2518 
# Theoretical number of reflections is about 2201 


_diffrn_reflns_theta_min         3.985
_diffrn_reflns_theta_max         76.114
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        76.114
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              27

_oxford_diffrn_Wilson_B_factor   2.31
_oxford_diffrn_Wilson_scale      0.03

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

_refine_diff_density_min         -0.18
_refine_diff_density_max         0.28


# 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         4368
_refine_ls_number_restraints     452
_refine_ls_number_parameters     309
_oxford_refine_ls_R_factor_ref   0.0346
_refine_ls_wR_factor_ref         0.0829
_refine_ls_goodness_of_fit_ref   1.0093
_refine_ls_shift/su_max          0.0007806
_refine_ls_shift/su_mean         0.0000446


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4370
_refine_ls_R_factor_all          0.0347
_refine_ls_wR_factor_all         0.0852

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4106
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_gt          0.0796

_refine_ls_abs_structure_Flack   -0.007(12)
_refine_ls_abs_structure_details 'Flack (1983), 1855 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    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.38P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
N1 N 0.59566(14) 0.62575(10) 0.49096(5) 0.0223 1.0000 Uani D . . . . .
C2 C 0.52451(16) 0.57212(10) 0.43513(6) 0.0241 1.0000 Uani D . . . . .
C3 C 0.59405(17) 0.63063(14) 0.37943(7) 0.0254 0.759(6) Uani D . P 1 1 .
C4 C 0.4989(3) 0.7019(3) 0.34400(15) 0.0413 0.759(6) Uani D . P 1 1 .
C5 C 0.5591(3) 0.7567(3) 0.29272(12) 0.0521 0.759(6) Uani D . P 1 1 .
C6 C 0.7186(4) 0.7367(3) 0.27662(13) 0.0441 0.759(6) Uani D . P 1 1 .
C7 C 0.8172(2) 0.66354(14) 0.31068(7) 0.0300 0.759(6) Uani D . P 1 1 .
C8 C 0.7535(2) 0.6105(2) 0.36216(11) 0.0256 0.759(6) Uani D . P 1 1 .
C9 C 0.4536(3) 0.8387(3) 0.25547(12) 0.0716 0.759(6) Uani D . P 1 1 .
C10 C 0.4888(6) 0.9638(3) 0.2693(2) 0.0854 0.759(6) Uani D . P 1 1 .
C11 C 0.98519(19) 0.63547(14) 0.28998(7) 0.0382 1.0000 Uani D . . . . .
C12 C 0.9874(3) 0.52912(19) 0.24834(9) 0.0471 1.0000 Uani D . . . . .
C13 C 0.5352(2) 0.43936(13) 0.43452(7) 0.0247 1.0000 Uani . . . . . .
C14 C 0.6770(2) 0.38458(15) 0.44972(7) 0.0276 1.0000 Uani . . . . . .
C15 C 0.6925(2) 0.26089(15) 0.44735(8) 0.0309 1.0000 Uani . . . . . .
C16 C 0.5665(2) 0.19316(14) 0.42945(8) 0.0320 1.0000 Uani . . . . . .
C17 C 0.4179(2) 0.24530(14) 0.41386(7) 0.0275 1.0000 Uani . . . . . .
C18 C 0.2846(2) 0.17551(15) 0.39666(8) 0.0327 1.0000 Uani . . . . . .
C19 C 0.1394(2) 0.22376(17) 0.38462(8) 0.0356 1.0000 Uani . . . . . .
C20 C 0.1194(2) 0.34673(17) 0.38795(8) 0.0346 1.0000 Uani . . . . . .
C21 C 0.2459(2) 0.41741(15) 0.40288(8) 0.0302 1.0000 Uani . . . . . .
C22 C 0.3999(2) 0.37040(14) 0.41660(7) 0.0255 1.0000 Uani . . . . . .
C23 C 0.5406(2) 0.57560(14) 0.55058(7) 0.0253 1.0000 Uani . . . . . .
C24 C 0.6255(2) 0.64388(16) 0.59997(7) 0.0330 1.0000 Uani . . . . . .
C25 C 0.3603(2) 0.58033(17) 0.55689(8) 0.0335 1.0000 Uani . . . . . .
Cl26 Cl 0.97101(4) 0.61438(3) 0.501703(19) 0.0299 1.0000 Uani . . . . . .
C103 C 0.5940(3) 0.6313(2) 0.37920(16) 0.0321 0.241(6) Uani D . P 1 2 .
C104 C 0.5060(6) 0.7136(7) 0.3482(3) 0.0407 0.241(6) Uani D . P 1 2 .
C105 C 0.5687(6) 0.7706(6) 0.2977(3) 0.0483 0.241(6) Uani D . P 1 2 .
C106 C 0.7248(7) 0.7452(7) 0.2801(3) 0.0412 0.241(6) Uani D . P 1 2 .
C107 C 0.8165(5) 0.6636(2) 0.31053(12) 0.0358 0.241(6) Uani D . P 1 2 .
C108 C 0.7502(7) 0.6075(6) 0.3607(3) 0.0352 0.241(6) Uani D . P 1 2 .
C109 C 0.4720(6) 0.8604(5) 0.2647(2) 0.0584 0.241(6) Uani D . P 1 2 .
C110 C 0.3551(12) 0.8215(9) 0.2210(4) 0.0650 0.241(6) Uani D . P 1 2 .
H11 H 0.7049 0.6233 0.4885 0.0326 1.0000 Uiso R . . . . .
H12 H 0.5689 0.7035 0.4905 0.0318 1.0000 Uiso R . . . . .
H21 H 0.4144 0.5929 0.4364 0.0257 0.759(6) Uiso R . P 1 1 .
H22 H 0.4114 0.5922 0.4360 0.0280 0.241(6) Uiso R . P 1 2 .
H41 H 0.3928 0.7140 0.3555 0.0495 0.759(6) Uiso R . P 1 1 .
H61 H 0.7624 0.7716 0.2419 0.0531 0.759(6) Uiso R . P 1 1 .
H81 H 0.8181 0.5605 0.3840 0.0312 0.759(6) Uiso R . P 1 1 .
H91 H 0.4692 0.8198 0.2122 0.0862 0.759(6) Uiso R . P 1 1 .
H92 H 0.3401 0.8225 0.2644 0.0854 0.759(6) Uiso R . P 1 1 .
H101 H 0.4794 0.9759 0.3117 0.1269 0.759(6) Uiso R . P 1 1 .
H102 H 0.4147 1.0100 0.2457 0.1281 0.759(6) Uiso R . P 1 1 .
H103 H 0.5979 0.9762 0.2565 0.1279 0.759(6) Uiso R . P 1 1 .
H111 H 1.0274 0.7029 0.2687 0.0464 0.241(6) Uiso R . P 1 2 .
H112 H 1.0522 0.6189 0.3250 0.0458 0.241(6) Uiso R . P 1 2 .
H113 H 1.0243 0.7037 0.2688 0.0471 0.759(6) Uiso R . P 1 1 .
H114 H 1.0548 0.6191 0.3247 0.0454 0.759(6) Uiso R . P 1 1 .
H121 H 1.0915 0.5182 0.2319 0.0707 1.0000 Uiso R . . . . .
H122 H 0.9151 0.5443 0.2139 0.0703 1.0000 Uiso R . . . . .
H123 H 0.9515 0.4584 0.2682 0.0694 1.0000 Uiso R . . . . .
H141 H 0.7656 0.4293 0.4631 0.0325 1.0000 Uiso R . . . . .
H151 H 0.7918 0.2277 0.4595 0.0352 1.0000 Uiso R . . . . .
H161 H 0.5738 0.1102 0.4281 0.0372 1.0000 Uiso R . . . . .
H181 H 0.2992 0.0926 0.3936 0.0391 1.0000 Uiso R . . . . .
H191 H 0.0493 0.1767 0.3734 0.0437 1.0000 Uiso R . . . . .
H201 H 0.0167 0.3796 0.3805 0.0420 1.0000 Uiso R . . . . .
H211 H 0.2291 0.4988 0.4053 0.0364 1.0000 Uiso R . . . . .
H231 H 0.5757 0.4946 0.5508 0.0293 1.0000 Uiso R . . . . .
H241 H 0.5959 0.7258 0.5983 0.0483 1.0000 Uiso R . . . . .
H242 H 0.7393 0.6387 0.5958 0.0479 1.0000 Uiso R . . . . .
H243 H 0.5943 0.6136 0.6389 0.0476 1.0000 Uiso R . . . . .
H251 H 0.3309 0.5520 0.5953 0.0494 1.0000 Uiso R . . . . .
H252 H 0.3227 0.6602 0.5540 0.0491 1.0000 Uiso R . . . . .
H253 H 0.3076 0.5315 0.5268 0.0491 1.0000 Uiso R . . . . .
H1041 H 0.4037 0.7321 0.3614 0.0487 0.241(6) Uiso R . P 1 2 .
H1061 H 0.7694 0.7835 0.2467 0.0491 0.241(6) Uiso R . P 1 2 .
H1081 H 0.8115 0.5532 0.3817 0.0421 0.241(6) Uiso R . P 1 2 .
H1091 H 0.5462 0.9116 0.2439 0.0698 0.241(6) Uiso R . P 1 2 .
H1092 H 0.4159 0.9060 0.2947 0.0700 0.241(6) Uiso R . P 1 2 .
H1101 H 0.4064 0.7670 0.1940 0.0979 0.241(6) Uiso R . P 1 2 .
H1102 H 0.3126 0.8877 0.1991 0.0980 0.241(6) Uiso R . P 1 2 .
H1103 H 0.2714 0.7816 0.2421 0.0979 0.241(6) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.51(9)
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
N1 . C2 . 1.5029(16) yes
N1 . C23 . 1.5123(19) yes
N1 . H11 . 0.912 no
N1 . H12 . 0.913 no
C2 . C3 . 1.519(2) yes
C2 . C13 . 1.5146(18) yes
C2 . H21 . 0.948 no
C2 . C13 . 1.5146(18) yes
C2 . C103 . 1.526(4) yes
C2 . H22 . 0.970 no
C3 . C4 . 1.381(3) yes
C3 . C8 . 1.401(2) yes
C4 . C5 . 1.391(3) yes
C4 . H41 . 0.930 no
C5 . C6 . 1.394(3) yes
C5 . C9 . 1.526(3) yes
C6 . C7 . 1.393(3) yes
C6 . H61 . 0.941 no
C7 . C8 . 1.397(2) yes
C7 . C11 . 1.507(2) yes
C8 . H81 . 0.921 no
C9 . C10 . 1.487(5) yes
C9 . H91 . 0.992 no
C9 . H92 . 0.983 no
C10 . H101 . 0.955 no
C10 . H102 . 0.966 no
C10 . H103 . 0.963 no
C11 . C12 . 1.523(2) yes
C11 . H113 . 0.965 no
C11 . H114 . 0.983 no
C11 . C12 . 1.523(2) yes
C11 . C107 . 1.512(4) yes
C11 . H111 . 0.968 no
C11 . H112 . 0.975 no
C12 . H121 . 0.949 no
C12 . H122 . 0.987 no
C12 . H123 . 0.965 no
C13 . C14 . 1.378(2) yes
C13 . C22 . 1.430(2) yes
C14 . C15 . 1.415(2) yes
C14 . H141 . 0.944 no
C15 . C16 . 1.362(3) yes
C15 . H151 . 0.948 no
C16 . C17 . 1.416(2) yes
C16 . H161 . 0.947 no
C17 . C18 . 1.418(2) yes
C17 . C22 . 1.434(2) yes
C18 . C19 . 1.355(3) yes
C18 . H181 . 0.955 no
C19 . C20 . 1.412(3) yes
C19 . H191 . 0.955 no
C20 . C21 . 1.367(2) yes
C20 . H201 . 0.948 no
C21 . C22 . 1.423(2) yes
C21 . H211 . 0.939 no
C23 . C24 . 1.519(2) yes
C23 . C25 . 1.509(2) yes
C23 . H231 . 0.968 no
C24 . H241 . 0.966 no
C24 . H242 . 0.955 no
C24 . H243 . 0.965 no
C25 . H251 . 0.943 no
C25 . H252 . 0.964 no
C25 . H253 . 0.974 no
C103 . C104 . 1.374(5) yes
C103 . C108 . 1.391(5) yes
C104 . C105 . 1.397(5) yes
C104 . H1041 . 0.926 no
C105 . C106 . 1.388(5) yes
C105 . C109 . 1.494(6) yes
C106 . C107 . 1.379(5) yes
C106 . H1061 . 0.935 no
C107 . C108 . 1.398(5) yes
C108 . H1081 . 0.928 no
C109 . C110 . 1.443(8) yes
C109 . H1091 . 0.968 no
C109 . H1092 . 0.965 no
C110 . H1101 . 0.962 no
C110 . H1102 . 0.964 no
C110 . H1103 . 0.954 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
C2 . N1 . C23 . 116.61(10) yes
C2 . N1 . H11 . 109.4 no
C23 . N1 . H11 . 110.1 no
C2 . N1 . H12 . 106.7 no
C23 . N1 . H12 . 107.6 no
H11 . N1 . H12 . 105.8 no
N1 . C2 . C3 . 109.99(6) yes
N1 . C2 . C13 . 112.94(11) yes
C3 . C2 . C13 . 114.09(12) yes
N1 . C2 . H21 . 104.8 no
C3 . C2 . H21 . 106.5 no
C13 . C2 . H21 . 107.9 no
N1 . C2 . C13 . 112.94(11) yes
N1 . C2 . C103 . 109.94(7) yes
C13 . C2 . C103 . 114.27(13) yes
N1 . C2 . H22 . 105.7 no
C13 . C2 . H22 . 107.0 no
C103 . C2 . H22 . 106.3 no
C2 . C3 . C4 . 120.13(5) yes
C2 . C3 . C8 . 120.81(5) yes
C4 . C3 . C8 . 119.03(5) yes
C3 . C4 . C5 . 121.46(6) yes
C3 . C4 . H41 . 118.4 no
C5 . C4 . H41 . 120.1 no
C4 . C5 . C6 . 118.70(5) yes
C4 . C5 . C9 . 120.62(5) yes
C6 . C5 . C9 . 120.67(5) yes
C5 . C6 . C7 . 121.38(6) yes
C5 . C6 . H61 . 120.7 no
C7 . C6 . H61 . 117.9 no
C6 . C7 . C8 . 118.55(5) yes
C6 . C7 . C11 . 120.62(5) yes
C8 . C7 . C11 . 120.69(5) yes
C3 . C8 . C7 . 120.86(6) yes
C3 . C8 . H81 . 120.7 no
C7 . C8 . H81 . 118.4 no
C5 . C9 . C10 . 111.15(10) yes
C5 . C9 . H91 . 108.4 no
C10 . C9 . H91 . 112.4 no
C5 . C9 . H92 . 109.3 no
C10 . C9 . H92 . 109.1 no
H91 . C9 . H92 . 106.3 no
C9 . C10 . H101 . 108.9 no
C9 . C10 . H102 . 106.5 no
H101 . C10 . H102 . 113.8 no
C9 . C10 . H103 . 105.4 no
H101 . C10 . H103 . 110.3 no
H102 . C10 . H103 . 111.4 no
C7 . C11 . C12 . 111.38(9) yes
C7 . C11 . H113 . 106.9 no
C12 . C11 . H113 . 109.9 no
C7 . C11 . H114 . 110.4 no
C12 . C11 . H114 . 108.5 no
H113 . C11 . H114 . 109.6 no
C12 . C11 . C107 . 111.26(10) yes
C12 . C11 . H111 . 109.3 no
C107 . C11 . H111 . 108.4 no
C12 . C11 . H112 . 108.8 no
C107 . C11 . H112 . 109.5 no
H111 . C11 . H112 . 109.5 no
C11 . C12 . H121 . 110.4 no
C11 . C12 . H122 . 108.8 no
H121 . C12 . H122 . 106.5 no
C11 . C12 . H123 . 112.5 no
H121 . C12 . H123 . 110.4 no
H122 . C12 . H123 . 108.0 no
C2 . C13 . C14 . 120.01(14) yes
C2 . C13 . C22 . 120.27(14) yes
C14 . C13 . C22 . 119.70(14) yes
C13 . C14 . C15 . 121.31(16) yes
C13 . C14 . H141 . 120.2 no
C15 . C14 . H141 . 118.5 no
C14 . C15 . C16 . 120.25(16) yes
C14 . C15 . H151 . 117.8 no
C16 . C15 . H151 . 121.9 no
C15 . C16 . C17 . 120.52(15) yes
C15 . C16 . H161 . 121.6 no
C17 . C16 . H161 . 117.8 no
C16 . C17 . C18 . 121.04(15) yes
C16 . C17 . C22 . 119.88(15) yes
C18 . C17 . C22 . 119.06(16) yes
C17 . C18 . C19 . 121.68(16) yes
C17 . C18 . H181 . 118.3 no
C19 . C18 . H181 . 120.0 no
C18 . C19 . C20 . 119.80(17) yes
C18 . C19 . H191 . 121.7 no
C20 . C19 . H191 . 118.5 no
C19 . C20 . C21 . 120.36(17) yes
C19 . C20 . H201 . 119.3 no
C21 . C20 . H201 . 120.4 no
C20 . C21 . C22 . 121.70(16) yes
C20 . C21 . H211 . 118.7 no
C22 . C21 . H211 . 119.6 no
C17 . C22 . C13 . 118.32(15) yes
C17 . C22 . C21 . 117.35(15) yes
C13 . C22 . C21 . 124.30(14) yes
N1 . C23 . C24 . 107.25(13) yes
N1 . C23 . C25 . 111.70(14) yes
C24 . C23 . C25 . 112.23(15) yes
N1 . C23 . H231 . 105.8 no
C24 . C23 . H231 . 110.1 no
C25 . C23 . H231 . 109.5 no
C23 . C24 . H241 . 110.4 no
C23 . C24 . H242 . 111.2 no
H241 . C24 . H242 . 108.0 no
C23 . C24 . H243 . 109.7 no
H241 . C24 . H243 . 108.1 no
H242 . C24 . H243 . 109.4 no
C23 . C25 . H251 . 109.3 no
C23 . C25 . H252 . 110.6 no
H251 . C25 . H252 . 107.3 no
C23 . C25 . H253 . 111.4 no
H251 . C25 . H253 . 107.9 no
H252 . C25 . H253 . 110.3 no
C2 . C103 . C104 . 120.36(6) yes
C2 . C103 . C108 . 120.57(6) yes
C104 . C103 . C108 . 118.98(6) yes
C103 . C104 . C105 . 121.24(6) yes
C103 . C104 . H1041 . 119.3 no
C105 . C104 . H1041 . 119.5 no
C104 . C105 . C106 . 118.68(6) yes
C104 . C105 . C109 . 120.64(6) yes
C106 . C105 . C109 . 120.64(6) yes
C105 . C106 . C107 . 121.39(6) yes
C105 . C106 . H1061 . 119.8 no
C107 . C106 . H1061 . 118.8 no
C11 . C107 . C106 . 120.66(6) yes
C11 . C107 . C108 . 120.71(5) yes
C106 . C107 . C108 . 118.63(5) yes
C107 . C108 . C103 . 121.04(6) yes
C107 . C108 . H1081 . 119.1 no
C103 . C108 . H1081 . 119.8 no
C105 . C109 . C110 . 118.9(4) yes
C105 . C109 . H1091 . 107.6 no
C110 . C109 . H1091 . 107.2 no
C105 . C109 . H1092 . 107.0 no
C110 . C109 . H1092 . 107.6 no
H1091 . C109 . H1092 . 108.2 no
C109 . C110 . H1101 . 108.4 no
C109 . C110 . H1102 . 110.2 no
H1101 . C110 . H1102 . 110.7 no
C109 . C110 . H1103 . 108.0 no
H1101 . C110 . H1103 . 108.9 no
H1102 . C110 . H1103 . 110.5 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
C110 . H92 . C4 . 127 0.97 2.60 3.277(4) yes
C10 . H1091 . C6 . 127 0.95 2.56 3.222(4) yes
C10 . H1091 . C106 . 125 0.95 2.54 3.182(4) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-8 6 9 x .
3 11 13 x .
2 0 26 x .
####################################################################### 
# 
# 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_6791
_database_code_depnum_ccdc_archive 'CCDC 1811312'
_audit_update_record             
;
2017-12-14 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;
_audit_creation_date             2017-08-17
_audit_creation_method           CRYSTALS_ver_14.61_build_6320

_oxford_structure_analysis_title 6791
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   13.92750(10)
_cell_length_b                   18.66730(10)
_cell_length_c                   15.27460(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.7566(8)
_cell_angle_gamma                90
_cell_volume                     3713.47(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,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'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 '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            2

# Given Formula = C92 H76 Cl1 N2 O4 P2 
# Dc =      1.23 Fooo =   1442.00 Mu =     12.86 M =   1371.03
# Found Formula = C93 H78 Cl2 N2 O4 P2 
# Dc =      1.27 FOOO =   1492.00 Mu =     16.27 M =   1420.51

_chemical_formula_sum            'C93 H78 Cl2 N2 O4 P2'
_chemical_formula_moiety         '2(C46 H38 N O2 P), C H2 Cl2'
_chemical_compound_source        .
_chemical_formula_weight         1420.51


_cell_measurement_reflns_used    42789
_cell_measurement_theta_min      3
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1492
_exptl_absorpt_coefficient_mu    1.627

# Sheldrick geometric approximatio 0.88 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_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            102352
_reflns_number_total             15438
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_av_sigmaI/netI    0.0811
# Number of reflections without Friedels Law is 15438 
# Number of reflections with Friedels Law is 8008 
# Theoretical number of reflections is about 7782 

_diffrn_reflns_theta_min         3.094
_diffrn_reflns_theta_max         76.281
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        76.281
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -17
_reflns_limit_h_max              16
_reflns_limit_k_min              -23
_reflns_limit_k_max              23
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   2.23
_oxford_diffrn_Wilson_scale      0.04

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

_refine_diff_density_min         -0.41
_refine_diff_density_max         0.42


# 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         15438
_refine_ls_number_restraints     1
_refine_ls_number_parameters     929
_oxford_refine_ls_R_factor_ref   0.0475
_refine_ls_wR_factor_ref         0.1194
_refine_ls_goodness_of_fit_ref   1.0071
_refine_ls_shift/su_max          0.0006632
_refine_ls_shift/su_mean         0.0000461


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        15438
_refine_ls_R_factor_all          0.0475
_refine_ls_wR_factor_all         0.1194

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                14631
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_gt          0.1169

_refine_ls_abs_structure_Flack   0.001(11)
_refine_ls_abs_structure_details 'Flack (1983), 7430 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    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 2.24P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
P1 P 0.4624 0.5000 0.6088 0.0212 1.0000 Uani . . . . . .
O2 O 0.4093 0.4243 0.6272 0.0243 1.0000 Uani . . . . . .
C3 C 0.3364 0.4188 0.6694 0.0217 1.0000 Uani . . . . . .
C4 C 0.3631 0.3793 0.7535 0.0265 1.0000 Uani . . . . . .
C5 C 0.2952 0.3742 0.7991 0.0288 1.0000 Uani . . . . . .
C6 C 0.1998 0.4097 0.7649 0.0261 1.0000 Uani . . . . . .
C7 C 0.1323 0.4100 0.8158 0.0335 1.0000 Uani . . . . . .
C8 C 0.0420 0.4466 0.7841 0.0365 1.0000 Uani . . . . . .
C9 C 0.0132 0.4840 0.6993 0.0318 1.0000 Uani . . . . . .
C10 C 0.0755 0.4839 0.6471 0.0253 1.0000 Uani . . . . . .
C11 C 0.1711 0.4466 0.6783 0.0213 1.0000 Uani . . . . . .
C12 C 0.2404 0.4488 0.6281 0.0204 1.0000 Uani . . . . . .
C13 C 0.2143 0.4864 0.5368 0.0196 1.0000 Uani . . . . . .
C14 C 0.1271 0.4674 0.4565 0.0227 1.0000 Uani . . . . . .
C15 C 0.0658 0.4064 0.4543 0.0276 1.0000 Uani . . . . . .
C16 C -0.0168 0.3900 0.3762 0.0348 1.0000 Uani . . . . . .
C17 C -0.0432 0.4333 0.2963 0.0390 1.0000 Uani . . . . . .
C18 C 0.0148 0.4915 0.2946 0.0343 1.0000 Uani . . . . . .
C19 C 0.1026 0.5098 0.3736 0.0263 1.0000 Uani . . . . . .
C20 C 0.1656 0.5687 0.3721 0.0298 1.0000 Uani . . . . . .
C21 C 0.2520 0.5836 0.4474 0.0274 1.0000 Uani . . . . . .
C22 C 0.2766 0.5413 0.5286 0.0225 1.0000 Uani . . . . . .
O23 O 0.3663 0.5560 0.6028 0.0231 1.0000 Uani . . . . . .
N24 N 0.5429 0.5265 0.7124 0.0233 1.0000 Uani . . . . . .
C25 C 0.6519 0.5388 0.7257 0.0236 1.0000 Uani . . . . . .
C26 C 0.5107 0.5360 0.7950 0.0289 1.0000 Uani . . . . . .
C27 C 0.5211 0.6128 0.8297 0.0536 1.0000 Uani . . . . . .
C28 C 0.5677 0.4849 0.8748 0.0471 1.0000 Uani . . . . . .
C29 C 0.6772 0.6171 0.7146 0.0232 1.0000 Uani . . . . . .
C30 C 0.6055 0.6627 0.6598 0.0249 1.0000 Uani . . . . . .
C31 C 0.6277 0.7359 0.6471 0.0250 1.0000 Uani . . . . . .
C32 C 0.5520 0.7800 0.5843 0.0302 1.0000 Uani . . . . . .
C33 C 0.5732 0.8499 0.5692 0.0348 1.0000 Uani . . . . . .
C34 C 0.6702 0.8779 0.6177 0.0378 1.0000 Uani . . . . . .
C35 C 0.7455 0.8362 0.6799 0.0327 1.0000 Uani . . . . . .
C36 C 0.7267 0.7636 0.6947 0.0264 1.0000 Uani . . . . . .
C37 C 0.8062 0.7151 0.7534 0.0258 1.0000 Uani . . . . . .
C38 C 0.9079 0.7380 0.7982 0.0328 1.0000 Uani . . . . . .
C39 C 0.9837 0.6914 0.8479 0.0363 1.0000 Uani . . . . . .
C40 C 0.9612 0.6193 0.8531 0.0351 1.0000 Uani . . . . . .
C41 C 0.8617 0.5952 0.8117 0.0291 1.0000 Uani . . . . . .
H41 H 0.4259 0.3557 0.7767 0.0306 1.0000 Uiso R . . . . .
C42 C 0.7816 0.6424 0.7608 0.0239 1.0000 Uani . . . . . .
C43 C 0.6883 0.4886 0.6640 0.0253 1.0000 Uani . . . . . .
C44 C 0.7226 0.5137 0.5952 0.0272 1.0000 Uani . . . . . .
C45 C 0.7574 0.4673 0.5413 0.0301 1.0000 Uani . . . . . .
C46 C 0.7555 0.3941 0.5578 0.0334 1.0000 Uani . . . . . .
C47 C 0.7198 0.3670 0.6254 0.0324 1.0000 Uani . . . . . .
C48 C 0.6877 0.4150 0.6792 0.0297 1.0000 Uani . . . . . .
C49 C 0.7972 0.4965 0.4693 0.0386 1.0000 Uani . . . . . .
C50 C 0.7161 0.2872 0.6413 0.0479 1.0000 Uani . . . . . .
P51 P 0.4478 1.1163 0.8475 0.0204 1.0000 Uani . . . . . .
H51 H 0.3119 0.3473 0.8526 0.0335 1.0000 Uiso R . . . . .
O52 O 0.3445 1.0644 0.7973 0.0222 1.0000 Uani . . . . . .
C53 C 0.2624 1.0867 0.8221 0.0217 1.0000 Uani . . . . . .
C54 C 0.2462 1.0518 0.8971 0.0276 1.0000 Uani . . . . . .
C55 C 0.1695 1.0746 0.9265 0.0303 1.0000 Uani . . . . . .
C56 C 0.1070 1.1339 0.8829 0.0277 1.0000 Uani . . . . . .
C57 C 0.0282 1.1589 0.9139 0.0356 1.0000 Uani . . . . . .
C58 C -0.0298 1.2169 0.8730 0.0413 1.0000 Uani . . . . . .
C59 C -0.0108 1.2535 0.8001 0.0385 1.0000 Uani . . . . . .
C60 C 0.0641 1.2301 0.7676 0.0292 1.0000 Uani . . . . . .
C61 C 0.1232 1.1688 0.8061 0.0225 1.0000 Uani . . . . . .
C62 C 0.2017 1.1423 0.7737 0.0202 1.0000 Uani . . . . . .
C63 C 0.2235 1.1750 0.6942 0.0200 1.0000 Uani . . . . . .
C64 C 0.1462 1.1801 0.6023 0.0213 1.0000 Uani . . . . . .
C65 C 0.0470 1.1502 0.5800 0.0245 1.0000 Uani . . . . . .
C66 C -0.0245 1.1546 0.4912 0.0311 1.0000 Uani . . . . . .
C67 C 0.0005 1.1884 0.4197 0.0373 1.0000 Uani . . . . . .
C68 C 0.0949 1.2174 0.4385 0.0331 1.0000 Uani . . . . . .
C69 C 0.1711 1.2136 0.5295 0.0242 1.0000 Uani . . . . . .
C70 C 0.2707 1.2417 0.5488 0.0272 1.0000 Uani . . . . . .
C71 C 0.3446 1.2338 0.6349 0.0243 1.0000 Uani . . . . . .
H71 H 0.1521 0.3854 0.8732 0.0401 1.0000 Uiso R . . . . .
C72 C 0.3212 1.1983 0.7065 0.0206 1.0000 Uani . . . . . .
O73 O 0.3999 1.1923 0.7927 0.0229 1.0000 Uani . . . . . .
N74 N 0.5214 1.0825 0.7930 0.0226 1.0000 Uani . . . . . .
C75 C 0.6298 1.0666 0.8474 0.0229 1.0000 Uani . . . . . .
C76 C 0.4839 1.0706 0.6901 0.0286 1.0000 Uani . . . . . .
C77 C 0.4846 0.9918 0.6657 0.0501 1.0000 Uani . . . . . .
C78 C 0.5422 1.1160 0.6427 0.0509 1.0000 Uani . . . . . .
C79 C 0.6501 0.9890 0.8800 0.0226 1.0000 Uani . . . . . .
C80 C 0.5772 0.9480 0.8942 0.0238 1.0000 Uani . . . . . .
C81 C 0.5956 0.8761 0.9288 0.0234 1.0000 Uani . . . . . .
H81 H -0.0011 0.4471 0.8190 0.0440 1.0000 Uiso R . . . . .
C82 C 0.5193 0.8369 0.9487 0.0296 1.0000 Uani . . . . . .
C83 C 0.5377 0.7681 0.9827 0.0307 1.0000 Uani . . . . . .
C84 C 0.6332 0.7365 0.9975 0.0297 1.0000 Uani . . . . . .
C85 C 0.7089 0.7733 0.9782 0.0274 1.0000 Uani . . . . . .
C86 C 0.6927 0.8446 0.9447 0.0231 1.0000 Uani . . . . . .
C87 C 0.7731 0.8875 0.9308 0.0221 1.0000 Uani . . . . . .
C88 C 0.8729 0.8605 0.9501 0.0285 1.0000 Uani . . . . . .
C89 C 0.9502 0.9021 0.9428 0.0343 1.0000 Uani . . . . . .
C90 C 0.9306 0.9737 0.9147 0.0329 1.0000 Uani . . . . . .
C91 C 0.8341 1.0018 0.8941 0.0291 1.0000 Uani . . . . . .
H91 H -0.0490 0.5099 0.6780 0.0387 1.0000 Uiso R . . . . .
C92 C 0.7525 0.9599 0.9006 0.0219 1.0000 Uani . . . . . .
C93 C 0.6734 1.1190 0.9288 0.0263 1.0000 Uani . . . . . .
C94 C 0.6997 1.0979 1.0215 0.0290 1.0000 Uani . . . . . .
C95 C 0.7350 1.1469 1.0946 0.0349 1.0000 Uani . . . . . .
C96 C 0.7430 1.2184 1.0724 0.0403 1.0000 Uani . . . . . .
C97 C 0.7196 1.2412 0.9812 0.0412 1.0000 Uani . . . . . .
C98 C 0.6850 1.1911 0.9092 0.0333 1.0000 Uani . . . . . .
C99 C 0.7648 1.1221 1.1945 0.0483 1.0000 Uani . . . . . .
C100 C 0.7309 1.3186 0.9588 0.0657 1.0000 Uani . . . . . .
Cl101 Cl 0.2949 0.8595 0.7369 0.0578 1.0000 Uani . . . . . .
H101 H 0.0548 0.5086 0.5892 0.0298 1.0000 Uiso R . . . . .
C102 C 0.3752 0.7991 0.7081 0.0698 1.0000 Uani . . . . . .
Cl103 Cl 0.3069 0.7356 0.6254 0.0633 1.0000 Uani . . . . . .
H151 H 0.0828 0.3770 0.5073 0.0330 1.0000 Uiso R . . . . .
H161 H -0.0560 0.3484 0.3774 0.0418 1.0000 Uiso R . . . . .
H171 H -0.1006 0.4217 0.2431 0.0470 1.0000 Uiso R . . . . .
H181 H -0.0047 0.5204 0.2404 0.0419 1.0000 Uiso R . . . . .
H201 H 0.1473 0.5975 0.3183 0.0360 1.0000 Uiso R . . . . .
H211 H 0.2949 0.6223 0.4458 0.0326 1.0000 Uiso R . . . . .
H251 H 0.6924 0.5248 0.7927 0.0278 1.0000 Uiso R . . . . .
H261 H 0.4373 0.5235 0.7728 0.0342 1.0000 Uiso R . . . . .
H271 H 0.4835 0.6438 0.7799 0.0793 1.0000 Uiso R . . . . .
H272 H 0.5917 0.6272 0.8538 0.0802 1.0000 Uiso R . . . . .
H273 H 0.4928 0.6146 0.8792 0.0801 1.0000 Uiso R . . . . .
H281 H 0.5634 0.4366 0.8490 0.0712 1.0000 Uiso R . . . . .
H282 H 0.6390 0.4998 0.9019 0.0708 1.0000 Uiso R . . . . .
H283 H 0.5351 0.4855 0.9215 0.0703 1.0000 Uiso R . . . . .
H301 H 0.5372 0.6462 0.6292 0.0299 1.0000 Uiso R . . . . .
H321 H 0.4870 0.7616 0.5532 0.0357 1.0000 Uiso R . . . . .
H331 H 0.5218 0.8781 0.5274 0.0421 1.0000 Uiso R . . . . .
H341 H 0.6845 0.9258 0.6110 0.0450 1.0000 Uiso R . . . . .
H351 H 0.8117 0.8568 0.7129 0.0384 1.0000 Uiso R . . . . .
H381 H 0.9222 0.7871 0.7931 0.0388 1.0000 Uiso R . . . . .
H391 H 1.0496 0.7081 0.8779 0.0440 1.0000 Uiso R . . . . .
H401 H 1.0127 0.5862 0.8841 0.0420 1.0000 Uiso R . . . . .
H411 H 0.8466 0.5470 0.8164 0.0344 1.0000 Uiso R . . . . .
H441 H 0.7236 0.5639 0.5848 0.0326 1.0000 Uiso R . . . . .
H461 H 0.7785 0.3632 0.5220 0.0400 1.0000 Uiso R . . . . .
H481 H 0.6654 0.3992 0.7268 0.0357 1.0000 Uiso R . . . . .
H491 H 0.8501 0.4660 0.4647 0.0583 1.0000 Uiso R . . . . .
H492 H 0.8268 0.5424 0.4887 0.0597 1.0000 Uiso R . . . . .
H493 H 0.7459 0.5016 0.4092 0.0589 1.0000 Uiso R . . . . .
H501 H 0.7317 0.2767 0.7064 0.0717 1.0000 Uiso R . . . . .
H502 H 0.7637 0.2613 0.6200 0.0722 1.0000 Uiso R . . . . .
H503 H 0.6486 0.2669 0.6088 0.0725 1.0000 Uiso R . . . . .
H541 H 0.2878 1.0128 0.9269 0.0325 1.0000 Uiso R . . . . .
H551 H 0.1602 1.0517 0.9776 0.0360 1.0000 Uiso R . . . . .
H571 H 0.0177 1.1347 0.9637 0.0420 1.0000 Uiso R . . . . .
H581 H -0.0838 1.2319 0.8929 0.0497 1.0000 Uiso R . . . . .
H591 H -0.0498 1.2944 0.7725 0.0460 1.0000 Uiso R . . . . .
H601 H 0.0766 1.2532 0.7185 0.0352 1.0000 Uiso R . . . . .
H651 H 0.0317 1.1274 0.6272 0.0282 1.0000 Uiso R . . . . .
H661 H -0.0906 1.1349 0.4780 0.0368 1.0000 Uiso R . . . . .
H671 H -0.0488 1.1916 0.3594 0.0456 1.0000 Uiso R . . . . .
H681 H 0.1100 1.2394 0.3902 0.0406 1.0000 Uiso R . . . . .
H701 H 0.2872 1.2658 0.5018 0.0334 1.0000 Uiso R . . . . .
H711 H 0.4111 1.2515 0.6480 0.0285 1.0000 Uiso R . . . . .
H751 H 0.6669 1.0744 0.8030 0.0273 1.0000 Uiso R . . . . .
H761 H 0.4112 1.0875 0.6658 0.0323 1.0000 Uiso R . . . . .
H771 H 0.4558 0.9875 0.5985 0.0744 1.0000 Uiso R . . . . .
H772 H 0.5541 0.9740 0.6898 0.0748 1.0000 Uiso R . . . . .
H773 H 0.4429 0.9660 0.6934 0.0745 1.0000 Uiso R . . . . .
H781 H 0.6095 1.0955 0.6544 0.0758 1.0000 Uiso R . . . . .
H782 H 0.5498 1.1643 0.6668 0.0759 1.0000 Uiso R . . . . .
H783 H 0.5040 1.1157 0.5751 0.0756 1.0000 Uiso R . . . . .
H801 H 0.5103 0.9673 0.8819 0.0291 1.0000 Uiso R . . . . .
H821 H 0.4566 0.8588 0.9400 0.0355 1.0000 Uiso R . . . . .
H831 H 0.4858 0.7421 0.9953 0.0363 1.0000 Uiso R . . . . .
H841 H 0.6476 0.6890 1.0202 0.0365 1.0000 Uiso R . . . . .
H851 H 0.7715 0.7510 0.9862 0.0336 1.0000 Uiso R . . . . .
H881 H 0.8866 0.8129 0.9697 0.0338 1.0000 Uiso R . . . . .
H891 H 1.0165 0.8827 0.9567 0.0404 1.0000 Uiso R . . . . .
H901 H 0.9846 1.0022 0.9096 0.0392 1.0000 Uiso R . . . . .
H911 H 0.8209 1.0506 0.8736 0.0350 1.0000 Uiso R . . . . .
H941 H 0.6919 1.0503 1.0359 0.0346 1.0000 Uiso R . . . . .
H961 H 0.7643 1.2526 1.1203 0.0482 1.0000 Uiso R . . . . .
H981 H 0.6674 1.2062 0.8457 0.0400 1.0000 Uiso R . . . . .
H991 H 0.7610 1.1604 1.2350 0.0726 1.0000 Uiso R . . . . .
H992 H 0.8345 1.1044 1.2172 0.0724 1.0000 Uiso R . . . . .
H993 H 0.7227 1.0826 1.1998 0.0723 1.0000 Uiso R . . . . .
H1001 H 0.6819 1.3485 0.9715 0.0990 1.0000 Uiso R . . . . .
H1002 H 0.7973 1.3357 0.9964 0.0993 1.0000 Uiso R . . . . .
H1003 H 0.7230 1.3260 0.8947 0.0991 1.0000 Uiso R . . . . .
H1021 H 0.4201 0.8254 0.6845 0.0845 1.0000 Uiso R . . . . .
H1022 H 0.4159 0.7738 0.7658 0.0846 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.840
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
P1 . O2 . 1.664 yes
P1 . O23 . 1.674 yes
P1 . N24 . 1.658 yes
O2 . C3 . 1.387 yes
C3 . C4 . 1.411 yes
C3 . C12 . 1.379 yes
C4 . C5 . 1.363 yes
C4 . H41 . 0.930 no
C5 . C6 . 1.410 yes
C5 . H51 . 0.916 no
C6 . C7 . 1.416 yes
C6 . C11 . 1.419 yes
C7 . C8 . 1.360 yes
C7 . H71 . 0.941 no
C8 . C9 . 1.399 yes
C8 . H81 . 0.933 no
C9 . C10 . 1.372 yes
C9 . H91 . 0.943 no
C10 . C11 . 1.426 yes
C10 . H101 . 0.946 no
C11 . C12 . 1.431 yes
C12 . C13 . 1.486 yes
C13 . C14 . 1.432 yes
C13 . C22 . 1.378 yes
C14 . C15 . 1.417 yes
C14 . C19 . 1.427 yes
C15 . C16 . 1.367 yes
C15 . H151 . 0.935 no
C16 . C17 . 1.400 yes
C16 . H161 . 0.953 no
C17 . C18 . 1.360 yes
C17 . H171 . 0.941 no
C18 . C19 . 1.421 yes
C18 . H181 . 0.944 no
C19 . C20 . 1.412 yes
C20 . C21 . 1.366 yes
C20 . H201 . 0.939 no
C21 . C22 . 1.406 yes
C21 . H211 . 0.944 no
C22 . O23 . 1.385 yes
N24 . C25 . 1.476 yes
N24 . C26 . 1.492 yes
C25 . C29 . 1.526 yes
C25 . C43 . 1.537 yes
C25 . H251 . 1.013 no
C26 . C27 . 1.517 yes
C26 . C28 . 1.529 yes
C26 . H261 . 0.984 no
C27 . H271 . 0.953 no
C27 . H272 . 0.958 no
C27 . H273 . 0.969 no
C28 . H281 . 0.978 no
C28 . H282 . 0.971 no
C28 . H283 . 0.973 no
C29 . C30 . 1.354 yes
C29 . C42 . 1.452 yes
C30 . C31 . 1.429 yes
C30 . H301 . 0.950 no
C31 . C32 . 1.412 yes
C31 . C36 . 1.410 yes
C32 . C33 . 1.374 yes
C32 . H321 . 0.927 no
C33 . C34 . 1.393 yes
C33 . H331 . 0.935 no
C34 . C35 . 1.379 yes
C34 . H341 . 0.928 no
C35 . C36 . 1.412 yes
C35 . H351 . 0.961 no
C36 . C37 . 1.465 yes
C37 . C38 . 1.404 yes
C37 . C42 . 1.414 yes
C38 . C39 . 1.372 yes
C38 . H381 . 0.946 no
C39 . C40 . 1.390 yes
C39 . H391 . 0.924 no
C40 . C41 . 1.379 yes
C40 . H401 . 0.937 no
C41 . C42 . 1.417 yes
C41 . H411 . 0.932 no
C43 . C44 . 1.381 yes
C43 . C48 . 1.394 yes
C44 . C45 . 1.395 yes
C44 . H441 . 0.950 no
C45 . C46 . 1.390 yes
C45 . C49 . 1.499 yes
C46 . C47 . 1.390 yes
C46 . H461 . 0.927 no
C47 . C48 . 1.392 yes
C47 . C50 . 1.513 yes
C48 . H481 . 0.934 no
C49 . H491 . 0.953 no
C49 . H492 . 0.953 no
C49 . H493 . 0.948 no
C50 . H501 . 0.959 no
C50 . H502 . 0.965 no
C50 . H503 . 0.972 no
P51 . O52 . 1.677 yes
P51 . O73 . 1.663 yes
P51 . N74 . 1.658 yes
O52 . C53 . 1.391 yes
C53 . C54 . 1.403 yes
C53 . C62 . 1.377 yes
C54 . C55 . 1.365 yes
C54 . H541 . 0.942 no
C55 . C56 . 1.421 yes
C55 . H551 . 0.938 no
C56 . C57 . 1.420 yes
C56 . C61 . 1.427 yes
C57 . C58 . 1.364 yes
C57 . H571 . 0.938 no
C58 . C59 . 1.408 yes
C58 . H581 . 0.948 no
C59 . C60 . 1.376 yes
C59 . H591 . 0.945 no
C60 . C61 . 1.411 yes
C60 . H601 . 0.932 no
C61 . C62 . 1.439 yes
C62 . C63 . 1.483 yes
C63 . C64 . 1.439 yes
C63 . C72 . 1.376 yes
C64 . C65 . 1.416 yes
C64 . C69 . 1.421 yes
C65 . C66 . 1.371 yes
C65 . H651 . 0.925 no
C66 . C67 . 1.407 yes
C66 . H661 . 0.945 no
C67 . C68 . 1.356 yes
C67 . H671 . 0.936 no
C68 . C69 . 1.420 yes
C68 . H681 . 0.930 no
C69 . C70 . 1.414 yes
C70 . C71 . 1.361 yes
C70 . H701 . 0.942 no
C71 . C72 . 1.412 yes
C71 . H711 . 0.935 no
C72 . O73 . 1.388 yes
N74 . C75 . 1.473 yes
N74 . C76 . 1.486 yes
C75 . C79 . 1.524 yes
C75 . C93 . 1.529 yes
C75 . H751 . 0.997 no
C76 . C77 . 1.518 yes
C76 . C78 . 1.522 yes
C76 . H761 . 0.998 no
C77 . H771 . 0.965 no
C77 . H772 . 0.964 no
C77 . H773 . 0.960 no
C78 . H781 . 0.969 no
C78 . H782 . 0.966 no
C78 . H783 . 0.980 no
C79 . C80 . 1.349 yes
C79 . C92 . 1.452 yes
C80 . C81 . 1.432 yes
C80 . H801 . 0.953 no
C81 . C82 . 1.409 yes
C81 . C86 . 1.414 yes
C82 . C83 . 1.376 yes
C82 . H821 . 0.931 no
C83 . C84 . 1.398 yes
C83 . H831 . 0.946 no
C84 . C85 . 1.374 yes
C84 . H841 . 0.947 no
C85 . C86 . 1.415 yes
C85 . H851 . 0.934 no
C86 . C87 . 1.452 yes
C87 . C88 . 1.408 yes
C87 . C92 . 1.425 yes
C88 . C89 . 1.364 yes
C88 . H881 . 0.936 no
C89 . C90 . 1.400 yes
C89 . H891 . 0.943 no
C90 . C91 . 1.373 yes
C90 . H901 . 0.947 no
C91 . C92 . 1.411 yes
C91 . H911 . 0.959 no
C93 . C94 . 1.387 yes
C93 . C98 . 1.399 yes
C94 . C95 . 1.390 yes
C94 . H941 . 0.932 no
C95 . C96 . 1.392 yes
C95 . C99 . 1.506 yes
C96 . C97 . 1.380 yes
C96 . H961 . 0.936 no
C97 . C98 . 1.393 yes
C97 . C100 . 1.506 yes
C98 . H981 . 0.955 no
C99 . H991 . 0.958 no
C99 . H992 . 0.967 no
C99 . H993 . 0.963 no
C100 . H1001 . 0.954 no
C100 . H1002 . 0.954 no
C100 . H1003 . 0.956 no
Cl101 . C102 . 1.751 yes
C102 . Cl103 . 1.747 yes
C102 . H1021 . 0.962 no
C102 . H1022 . 0.983 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
O2 . P1 . O23 . 98.34 yes
O2 . P1 . N24 . 106.40 yes
O23 . P1 . N24 . 97.13 yes
P1 . O2 . C3 . 125.72 yes
O2 . C3 . C4 . 117.46 yes
O2 . C3 . C12 . 120.52 yes
C4 . C3 . C12 . 121.98 yes
C3 . C4 . C5 . 119.67 yes
C3 . C4 . H41 . 120.3 no
C5 . C4 . H41 . 120.0 no
C4 . C5 . C6 . 120.76 yes
C4 . C5 . H51 . 119.5 no
C6 . C5 . H51 . 119.7 no
C5 . C6 . C7 . 121.42 yes
C5 . C6 . C11 . 119.41 yes
C7 . C6 . C11 . 119.16 yes
C6 . C7 . C8 . 121.13 yes
C6 . C7 . H71 . 118.5 no
C8 . C7 . H71 . 120.4 no
C7 . C8 . C9 . 120.39 yes
C7 . C8 . H81 . 120.1 no
C9 . C8 . H81 . 119.5 no
C8 . C9 . C10 . 120.26 yes
C8 . C9 . H91 . 120.1 no
C10 . C9 . H91 . 119.7 no
C9 . C10 . C11 . 121.01 yes
C9 . C10 . H101 . 119.7 no
C11 . C10 . H101 . 119.3 no
C10 . C11 . C6 . 118.03 yes
C10 . C11 . C12 . 122.28 yes
C6 . C11 . C12 . 119.59 yes
C11 . C12 . C3 . 118.13 yes
C11 . C12 . C13 . 121.95 yes
C3 . C12 . C13 . 119.79 yes
C12 . C13 . C14 . 122.62 yes
C12 . C13 . C22 . 118.93 yes
C14 . C13 . C22 . 118.45 yes
C13 . C14 . C15 . 122.63 yes
C13 . C14 . C19 . 119.14 yes
C15 . C14 . C19 . 118.19 yes
C14 . C15 . C16 . 120.91 yes
C14 . C15 . H151 . 119.0 no
C16 . C15 . H151 . 120.0 no
C15 . C16 . C17 . 120.78 yes
C15 . C16 . H161 . 118.5 no
C17 . C16 . H161 . 120.8 no
C16 . C17 . C18 . 120.22 yes
C16 . C17 . H171 . 120.0 no
C18 . C17 . H171 . 119.7 no
C17 . C18 . C19 . 120.89 yes
C17 . C18 . H181 . 119.0 no
C19 . C18 . H181 . 120.1 no
C14 . C19 . C18 . 118.92 yes
C14 . C19 . C20 . 119.40 yes
C18 . C19 . C20 . 121.68 yes
C19 . C20 . C21 . 120.77 yes
C19 . C20 . H201 . 118.9 no
C21 . C20 . H201 . 120.4 no
C20 . C21 . C22 . 119.70 yes
C20 . C21 . H211 . 120.7 no
C22 . C21 . H211 . 119.6 no
C21 . C22 . C13 . 122.21 yes
C21 . C22 . O23 . 118.57 yes
C13 . C22 . O23 . 119.21 yes
C22 . O23 . P1 . 113.14 yes
P1 . N24 . C25 . 119.49 yes
P1 . N24 . C26 . 122.58 yes
C25 . N24 . C26 . 117.90 yes
N24 . C25 . C29 . 113.64 yes
N24 . C25 . C43 . 111.57 yes
C29 . C25 . C43 . 112.10 yes
N24 . C25 . H251 . 106.0 no
C29 . C25 . H251 . 106.9 no
C43 . C25 . H251 . 105.9 no
N24 . C26 . C27 . 112.82 yes
N24 . C26 . C28 . 111.89 yes
C27 . C26 . C28 . 110.62 yes
N24 . C26 . H261 . 105.5 no
C27 . C26 . H261 . 107.7 no
C28 . C26 . H261 . 108.0 no
C26 . C27 . H271 . 109.8 no
C26 . C27 . H272 . 111.0 no
H271 . C27 . H272 . 109.5 no
C26 . C27 . H273 . 106.9 no
H271 . C27 . H273 . 109.9 no
H272 . C27 . H273 . 109.7 no
C26 . C28 . H281 . 108.3 no
C26 . C28 . H282 . 109.0 no
H281 . C28 . H282 . 110.1 no
C26 . C28 . H283 . 109.4 no
H281 . C28 . H283 . 109.2 no
H282 . C28 . H283 . 110.9 no
C25 . C29 . C30 . 121.47 yes
C25 . C29 . C42 . 119.26 yes
C30 . C29 . C42 . 119.22 yes
C29 . C30 . C31 . 122.54 yes
C29 . C30 . H301 . 119.3 no
C31 . C30 . H301 . 118.1 no
C30 . C31 . C32 . 120.31 yes
C30 . C31 . C36 . 120.02 yes
C32 . C31 . C36 . 119.64 yes
C31 . C32 . C33 . 120.98 yes
C31 . C32 . H321 . 119.3 no
C33 . C32 . H321 . 119.7 no
C32 . C33 . C34 . 119.52 yes
C32 . C33 . H331 . 119.5 no
C34 . C33 . H331 . 121.0 no
C33 . C34 . C35 . 120.72 yes
C33 . C34 . H341 . 120.5 no
C35 . C34 . H341 . 118.7 no
C34 . C35 . C36 . 120.92 yes
C34 . C35 . H351 . 119.2 no
C36 . C35 . H351 . 119.8 no
C35 . C36 . C31 . 118.17 yes
C35 . C36 . C37 . 123.28 yes
C31 . C36 . C37 . 118.48 yes
C36 . C37 . C38 . 121.50 yes
C36 . C37 . C42 . 119.43 yes
C38 . C37 . C42 . 118.96 yes
C37 . C38 . C39 . 121.48 yes
C37 . C38 . H381 . 117.4 no
C39 . C38 . H381 . 121.1 no
C38 . C39 . C40 . 120.08 yes
C38 . C39 . H391 . 119.7 no
C40 . C39 . H391 . 120.3 no
C39 . C40 . C41 . 119.98 yes
C39 . C40 . H401 . 121.2 no
C41 . C40 . H401 . 118.8 no
C40 . C41 . C42 . 121.07 yes
C40 . C41 . H411 . 119.8 no
C42 . C41 . H411 . 119.2 no
C29 . C42 . C41 . 121.46 yes
C29 . C42 . C37 . 120.15 yes
C41 . C42 . C37 . 118.37 yes
C25 . C43 . C44 . 122.50 yes
C25 . C43 . C48 . 118.48 yes
C44 . C43 . C48 . 119.02 yes
C43 . C44 . C45 . 121.58 yes
C43 . C44 . H441 . 119.4 no
C45 . C44 . H441 . 119.1 no
C44 . C45 . C46 . 118.06 yes
C44 . C45 . C49 . 120.20 yes
C46 . C45 . C49 . 121.73 yes
C45 . C46 . C47 . 121.83 yes
C45 . C46 . H461 . 118.2 no
C47 . C46 . H461 . 120.0 no
C46 . C47 . C48 . 118.54 yes
C46 . C47 . C50 . 121.33 yes
C48 . C47 . C50 . 120.13 yes
C43 . C48 . C47 . 120.94 yes
C43 . C48 . H481 . 117.5 no
C47 . C48 . H481 . 121.5 no
C45 . C49 . H491 . 109.5 no
C45 . C49 . H492 . 109.4 no
H491 . C49 . H492 . 107.5 no
C45 . C49 . H493 . 113.5 no
H491 . C49 . H493 . 109.0 no
H492 . C49 . H493 . 107.7 no
C47 . C50 . H501 . 111.2 no
C47 . C50 . H502 . 111.9 no
H501 . C50 . H502 . 108.5 no
C47 . C50 . H503 . 112.5 no
H501 . C50 . H503 . 105.8 no
H502 . C50 . H503 . 106.8 no
O52 . P51 . O73 . 97.85 yes
O52 . P51 . N74 . 97.64 yes
O73 . P51 . N74 . 106.31 yes
P51 . O52 . C53 . 110.92 yes
O52 . C53 . C54 . 118.02 yes
O52 . C53 . C62 . 119.10 yes
C54 . C53 . C62 . 122.87 yes
C53 . C54 . C55 . 119.64 yes
C53 . C54 . H541 . 120.2 no
C55 . C54 . H541 . 120.1 no
C54 . C55 . C56 . 120.66 yes
C54 . C55 . H551 . 119.1 no
C56 . C55 . H551 . 120.2 no
C55 . C56 . C57 . 121.13 yes
C55 . C56 . C61 . 119.45 yes
C57 . C56 . C61 . 119.42 yes
C56 . C57 . C58 . 120.61 yes
C56 . C57 . H571 . 118.2 no
C58 . C57 . H571 . 121.1 no
C57 . C58 . C59 . 120.09 yes
C57 . C58 . H581 . 119.6 no
C59 . C58 . H581 . 120.3 no
C58 . C59 . C60 . 120.70 yes
C58 . C59 . H591 . 120.3 no
C60 . C59 . H591 . 119.0 no
C59 . C60 . C61 . 120.76 yes
C59 . C60 . H601 . 121.6 no
C61 . C60 . H601 . 117.6 no
C56 . C61 . C60 . 118.30 yes
C56 . C61 . C62 . 119.11 yes
C60 . C61 . C62 . 122.53 yes
C61 . C62 . C53 . 118.11 yes
C61 . C62 . C63 . 122.72 yes
C53 . C62 . C63 . 119.07 yes
C62 . C63 . C64 . 121.81 yes
C62 . C63 . C72 . 119.85 yes
C64 . C63 . C72 . 118.26 yes
C63 . C64 . C65 . 122.50 yes
C63 . C64 . C69 . 119.20 yes
C65 . C64 . C69 . 118.23 yes
C64 . C65 . C66 . 121.23 yes
C64 . C65 . H651 . 118.0 no
C66 . C65 . H651 . 120.8 no
C65 . C66 . C67 . 120.14 yes
C65 . C66 . H661 . 119.9 no
C67 . C66 . H661 . 120.0 no
C66 . C67 . C68 . 120.20 yes
C66 . C67 . H671 . 119.7 no
C68 . C67 . H671 . 120.1 no
C67 . C68 . C69 . 121.24 yes
C67 . C68 . H681 . 118.9 no
C69 . C68 . H681 . 119.9 no
C64 . C69 . C68 . 118.93 yes
C64 . C69 . C70 . 119.55 yes
C68 . C69 . C70 . 121.51 yes
C69 . C70 . C71 . 120.78 yes
C69 . C70 . H701 . 120.3 no
C71 . C70 . H701 . 118.9 no
C70 . C71 . C72 . 119.74 yes
C70 . C71 . H711 . 121.3 no
C72 . C71 . H711 . 118.9 no
C71 . C72 . C63 . 122.10 yes
C71 . C72 . O73 . 116.80 yes
C63 . C72 . O73 . 120.94 yes
C72 . O73 . P51 . 125.98 yes
P51 . N74 . C75 . 119.07 yes
P51 . N74 . C76 . 122.68 yes
C75 . N74 . C76 . 118.18 yes
N74 . C75 . C79 . 114.20 yes
N74 . C75 . C93 . 111.22 yes
C79 . C75 . C93 . 111.57 yes
N74 . C75 . H751 . 105.1 no
C79 . C75 . H751 . 106.3 no
C93 . C75 . H751 . 107.9 no
N74 . C76 . C77 . 111.95 yes
N74 . C76 . C78 . 111.89 yes
C77 . C76 . C78 . 111.82 yes
N74 . C76 . H761 . 106.0 no
C77 . C76 . H761 . 108.0 no
C78 . C76 . H761 . 106.8 no
C76 . C77 . H771 . 107.7 no
C76 . C77 . H772 . 109.5 no
H771 . C77 . H772 . 111.1 no
C76 . C77 . H773 . 108.7 no
H771 . C77 . H773 . 109.8 no
H772 . C77 . H773 . 109.9 no
C76 . C78 . H781 . 109.8 no
C76 . C78 . H782 . 110.1 no
H781 . C78 . H782 . 109.2 no
C76 . C78 . H783 . 108.5 no
H781 . C78 . H783 . 108.6 no
H782 . C78 . H783 . 110.6 no
C75 . C79 . C80 . 121.95 yes
C75 . C79 . C92 . 118.64 yes
C80 . C79 . C92 . 119.34 yes
C79 . C80 . C81 . 123.00 yes
C79 . C80 . H801 . 119.5 no
C81 . C80 . H801 . 117.5 no
C80 . C81 . C82 . 121.06 yes
C80 . C81 . C86 . 119.28 yes
C82 . C81 . C86 . 119.66 yes
C81 . C82 . C83 . 120.86 yes
C81 . C82 . H821 . 118.9 no
C83 . C82 . H821 . 120.2 no
C82 . C83 . C84 . 119.56 yes
C82 . C83 . H831 . 120.2 no
C84 . C83 . H831 . 120.2 no
C83 . C84 . C85 . 120.85 yes
C83 . C84 . H841 . 121.3 no
C85 . C84 . H841 . 117.9 no
C84 . C85 . C86 . 120.76 yes
C84 . C85 . H851 . 120.1 no
C86 . C85 . H851 . 119.2 no
C85 . C86 . C81 . 118.29 yes
C85 . C86 . C87 . 122.61 yes
C81 . C86 . C87 . 119.02 yes
C86 . C87 . C88 . 121.85 yes
C86 . C87 . C92 . 119.56 yes
C88 . C87 . C92 . 118.53 yes
C87 . C88 . C89 . 121.94 yes
C87 . C88 . H881 . 118.8 no
C89 . C88 . H881 . 119.3 no
C88 . C89 . C90 . 119.65 yes
C88 . C89 . H891 . 120.1 no
C90 . C89 . H891 . 120.3 no
C89 . C90 . C91 . 120.23 yes
C89 . C90 . H901 . 119.3 no
C91 . C90 . H901 . 120.5 no
C90 . C91 . C92 . 121.37 yes
C90 . C91 . H911 . 119.7 no
C92 . C91 . H911 . 118.9 no
C79 . C92 . C87 . 119.64 yes
C79 . C92 . C91 . 122.09 yes
C87 . C92 . C91 . 118.25 yes
C75 . C93 . C94 . 122.23 yes
C75 . C93 . C98 . 118.91 yes
C94 . C93 . C98 . 118.84 yes
C93 . C94 . C95 . 121.53 yes
C93 . C94 . H941 . 120.1 no
C95 . C94 . H941 . 118.3 no
C94 . C95 . C96 . 118.13 yes
C94 . C95 . C99 . 120.28 yes
C96 . C95 . C99 . 121.58 yes
C95 . C96 . C97 . 121.96 yes
C95 . C96 . H961 . 119.6 no
C97 . C96 . H961 . 118.4 no
C96 . C97 . C98 . 118.85 yes
C96 . C97 . C100 . 121.19 yes
C98 . C97 . C100 . 119.97 yes
C93 . C98 . C97 . 120.65 yes
C93 . C98 . H981 . 119.6 no
C97 . C98 . H981 . 119.7 no
C95 . C99 . H991 . 111.5 no
C95 . C99 . H992 . 110.4 no
H991 . C99 . H992 . 107.5 no
C95 . C99 . H993 . 111.3 no
H991 . C99 . H993 . 110.1 no
H992 . C99 . H993 . 105.8 no
C97 . C100 . H1001 . 112.1 no
C97 . C100 . H1002 . 110.0 no
H1001 . C100 . H1002 . 107.0 no
C97 . C100 . H1003 . 112.9 no
H1001 . C100 . H1003 . 107.0 no
H1002 . C100 . H1003 . 107.6 no
Cl101 . C102 . Cl103 . 112.73 yes
Cl101 . C102 . H1021 . 108.9 no
Cl103 . C102 . H1021 . 109.7 no
Cl101 . C102 . H1022 . 107.5 no
Cl103 . C102 . H1022 . 108.4 no
H1021 . C102 . H1022 . 109.7 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
C26 . H261 . C3 . 131 0.98 2.59 3.326(4) yes
####################################################################### 
# 
# 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_6790
_database_code_depnum_ccdc_archive 'CCDC 1811311'
_audit_update_record             
;
2017-12-14 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;
_audit_creation_date             2017-08-18
_audit_creation_method           CRYSTALS_ver_14.61_build_6320

_oxford_structure_analysis_title 6790
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
A disordered solvent molecule was found in the difference map.
The solvent molecule was disordered over a symmetry operation.
;

_cell_length_a                   24.2085(3)
_cell_length_b                   16.0031(2)
_cell_length_c                   8.82830(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3420.18(7)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2 '
_symmetry_space_group_name_Hall  'P 2 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z
x+1/2,-y+1/2,-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'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 '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            4

# Given Formula = C43 H36 Cl2 N1 O2 P1 
# Dc =      1.36 Fooo =   1464.00 Mu =     24.60 M =    700.64
# Found Formula = C42.45 H36.90 Cl0.90 N1 O2 P1 
# Dc =      1.27 FOOO =   1379.41 Mu =     16.49 M =    655.85

_chemical_formula_sum            'C42.45 H36.90 Cl0.90 N O2 P1'
_chemical_formula_moiety         'C42 H36 N O2 P, 0.449(C H2 Cl2'
_chemical_compound_source        .
_chemical_formula_weight         655.85


_cell_measurement_reflns_used    17491
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1379.412
_exptl_absorpt_coefficient_mu    1.649

# Sheldrick geometric approximatio 0.72 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_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       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_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            36120
_reflns_number_total             7115
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_sigmaI/netI    0.0556
# Number of reflections without Friedels Law is 7115 
# Number of reflections with Friedels Law is 4016 
# Theoretical number of reflections is about 3588 

_diffrn_reflns_theta_min         3.652
_diffrn_reflns_theta_max         76.378
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        74.850
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -30
_reflns_limit_h_max              30
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   2.79
_oxford_diffrn_Wilson_scale      0.05

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

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.34


# 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>-10.0\s(I)
_refine_ls_number_reflns         7115
_refine_ls_number_restraints     0
_refine_ls_number_parameters     438
_oxford_refine_ls_R_factor_ref   0.0375
_refine_ls_wR_factor_ref         0.0949
_refine_ls_goodness_of_fit_ref   1.0024
_refine_ls_shift/su_max          0.0008721
_refine_ls_shift/su_mean         0.0000986


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7115
_refine_ls_R_factor_all          0.0375
_refine_ls_wR_factor_all         0.0949

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6824
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_gt          0.0929

_refine_ls_abs_structure_Flack   -0.008(15)
_refine_ls_abs_structure_details 'Flack (1983), 3099 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    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.92P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
P1 P 0.2842 0.6239 0.6543 0.0302 1.0000 Uani . . . . . .
O2 O 0.2163 0.6445 0.6455 0.0278 1.0000 Uani . . . . . .
C3 C 0.1833 0.6092 0.7561 0.0262 1.0000 Uani . . . . . .
C4 C 0.1523 0.5374 0.7157 0.0301 1.0000 Uani . . . . . .
C5 C 0.1185 0.5004 0.8199 0.0320 1.0000 Uani . . . . . .
C6 C 0.1158 0.5316 0.9704 0.0280 1.0000 Uani . . . . . .
C7 C 0.0837 0.4916 1.0833 0.0378 1.0000 Uani . . . . . .
C8 C 0.0834 0.5191 1.2289 0.0436 1.0000 Uani . . . . . .
C9 C 0.1157 0.5886 1.2698 0.0404 1.0000 Uani . . . . . .
C10 C 0.1466 0.6298 1.1632 0.0327 1.0000 Uani . . . . . .
C11 C 0.1474 0.6033 1.0099 0.0261 1.0000 Uani . . . . . .
C12 C 0.1803 0.6448 0.8975 0.0245 1.0000 Uani . . . . . .
C13 C 0.2129 0.7216 0.9296 0.0267 1.0000 Uani . . . . . .
C14 C 0.1888 0.7956 0.9911 0.0327 1.0000 Uani . . . . . .
C15 C 0.1315 0.8039 1.0175 0.0427 1.0000 Uani . . . . . .
C16 C 0.1110 0.8749 1.0830 0.0683 1.0000 Uani . . . . . .
C17 C 0.1464 0.9417 1.1227 0.0823 1.0000 Uani . . . . . .
C18 C 0.2008 0.9366 1.0936 0.0663 1.0000 Uani . . . . . .
C19 C 0.2236 0.8651 1.0264 0.0448 1.0000 Uani . . . . . .
C20 C 0.2804 0.8602 0.9944 0.0492 1.0000 Uani . . . . . .
C21 C 0.3026 0.7918 0.9296 0.0426 1.0000 Uani . . . . . .
C22 C 0.2686 0.7224 0.8961 0.0321 1.0000 Uani . . . . . .
O23 O 0.2940 0.6539 0.8325 0.0345 1.0000 Uani . . . . . .
N24 N 0.3043 0.7030 0.5438 0.0278 1.0000 Uani . . . . . .
C25 C 0.3476 0.6868 0.4276 0.0272 1.0000 Uani . . . . . .
C26 C 0.2711 0.7818 0.5285 0.0299 1.0000 Uani . . . . . .
C27 C 0.3053 0.8614 0.5228 0.0456 1.0000 Uani . . . . . .
C28 C 0.2321 0.7771 0.3932 0.0440 1.0000 Uani . . . . . .
C29 C 0.3997 0.7391 0.4514 0.0292 1.0000 Uani . . . . . .
C30 C 0.4167 0.7618 0.5934 0.0385 1.0000 Uani . . . . . .
C31 C 0.4641 0.8114 0.6157 0.0440 1.0000 Uani . . . . . .
C32 C 0.4940 0.8380 0.4944 0.0450 1.0000 Uani . . . . . .
C33 C 0.4796 0.8142 0.3463 0.0361 1.0000 Uani . . . . . .
C34 C 0.5118 0.8390 0.2194 0.0452 1.0000 Uani . . . . . .
C35 C 0.4989 0.8134 0.0771 0.0500 1.0000 Uani . . . . . .
C36 C 0.4527 0.7624 0.0539 0.0464 1.0000 Uani . . . . . .
C37 C 0.4201 0.7373 0.1728 0.0370 1.0000 Uani . . . . . .
C38 C 0.4321 0.7632 0.3231 0.0301 1.0000 Uani . . . . . .
C43 C 0.3623 0.5936 0.4152 0.0299 1.0000 Uani . . . . . .
C44 C 0.3295 0.5392 0.3291 0.0350 1.0000 Uani . . . . . .
C45 C 0.3430 0.4543 0.3250 0.0423 1.0000 Uani . . . . . .
C46 C 0.3879 0.4221 0.4030 0.0430 1.0000 Uani . . . . . .
C47 C 0.4203 0.4764 0.4864 0.0445 1.0000 Uani . . . . . .
C48 C 0.4078 0.5612 0.4917 0.0384 1.0000 Uani . . . . . .
C49 C 0.2790 0.5688 0.2458 0.0478 1.0000 Uani . . . . . .
C50 C 0.4014 0.3295 0.3959 0.0639 1.0000 Uani . . . . . .
C61 C 0.5339 0.4647 0.0874 0.0704 0.4489 Uani . . P 1 -1 .
Cl62 Cl 0.4891 0.5491 0.1137 0.0645 0.4489 Uani . . P 1 -1 .
Cl63 Cl 0.5403 0.4333 -0.1001 0.0704 0.4489 Uani . . P 1 -1 .
H41 H 0.1550 0.5152 0.6172 0.0349 1.0000 Uiso R . . . . .
H51 H 0.0969 0.4543 0.7956 0.0380 1.0000 Uiso R . . . . .
H71 H 0.0631 0.4442 1.0528 0.0449 1.0000 Uiso R . . . . .
H81 H 0.0625 0.4919 1.3006 0.0515 1.0000 Uiso R . . . . .
H91 H 0.1168 0.6071 1.3713 0.0485 1.0000 Uiso R . . . . .
H101 H 0.1675 0.6750 1.1915 0.0385 1.0000 Uiso R . . . . .
H151 H 0.1074 0.7617 0.9900 0.0506 1.0000 Uiso R . . . . .
H161 H 0.0730 0.8811 1.0960 0.0818 1.0000 Uiso R . . . . .
H171 H 0.1315 0.9898 1.1689 0.0991 1.0000 Uiso R . . . . .
H181 H 0.2239 0.9838 1.1168 0.0795 1.0000 Uiso R . . . . .
H201 H 0.3032 0.9063 1.0200 0.0582 1.0000 Uiso R . . . . .
H211 H 0.3405 0.7886 0.9068 0.0516 1.0000 Uiso R . . . . .
H251 H 0.3321 0.7046 0.3296 0.0316 1.0000 Uiso R . . . . .
H261 H 0.2489 0.7837 0.6214 0.0339 1.0000 Uiso R . . . . .
H273 H 0.2809 0.9085 0.5196 0.0673 1.0000 Uiso R . . . . .
H271 H 0.3288 0.8680 0.6119 0.0661 1.0000 Uiso R . . . . .
H272 H 0.3279 0.8609 0.4331 0.0666 1.0000 Uiso R . . . . .
H281 H 0.2097 0.8253 0.3871 0.0646 1.0000 Uiso R . . . . .
H282 H 0.2514 0.7732 0.3020 0.0665 1.0000 Uiso R . . . . .
H283 H 0.2082 0.7287 0.4057 0.0652 1.0000 Uiso R . . . . .
H301 H 0.3969 0.7457 0.6794 0.0459 1.0000 Uiso R . . . . .
H311 H 0.4742 0.8252 0.7153 0.0529 1.0000 Uiso R . . . . .
H321 H 0.5254 0.8728 0.5086 0.0548 1.0000 Uiso R . . . . .
H341 H 0.5425 0.8724 0.2366 0.0542 1.0000 Uiso R . . . . .
H351 H 0.5213 0.8288 -0.0096 0.0603 1.0000 Uiso R . . . . .
H361 H 0.4431 0.7453 -0.0456 0.0565 1.0000 Uiso R . . . . .
H371 H 0.3888 0.7023 0.1529 0.0431 1.0000 Uiso R . . . . .
H451 H 0.3200 0.4181 0.2683 0.0519 1.0000 Uiso R . . . . .
H471 H 0.4494 0.4559 0.5450 0.0539 1.0000 Uiso R . . . . .
H481 H 0.4304 0.5962 0.5505 0.0450 1.0000 Uiso R . . . . .
H492 H 0.2609 0.5229 0.2000 0.0722 1.0000 Uiso R . . . . .
H493 H 0.2900 0.6095 0.1684 0.0729 1.0000 Uiso R . . . . .
H491 H 0.2547 0.5945 0.3181 0.0716 1.0000 Uiso R . . . . .
H503 H 0.4133 0.3103 0.4922 0.0956 1.0000 Uiso R . . . . .
H501 H 0.4319 0.3230 0.3240 0.0969 1.0000 Uiso R . . . . .
H502 H 0.3710 0.2955 0.3651 0.0971 1.0000 Uiso R . . . . .
H611 H 0.5188 0.4190 0.1521 0.0852 0.4489 Uiso R . P 1 -1 .
H612 H 0.5693 0.4814 0.1249 0.0851 0.4489 Uiso R . P 1 -1 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.387
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
P1 . O2 . 1.679 yes
P1 . O23 . 1.662 yes
P1 . N24 . 1.670 yes
O2 . C3 . 1.383 yes
C3 . C4 . 1.417 yes
C3 . C12 . 1.374 yes
C4 . C5 . 1.366 yes
C4 . H41 . 0.942 no
C5 . C6 . 1.421 yes
C5 . H51 . 0.931 no
C6 . C7 . 1.417 yes
C6 . C11 . 1.422 yes
C7 . C8 . 1.359 yes
C7 . H71 . 0.947 no
C8 . C9 . 1.407 yes
C8 . H81 . 0.919 no
C9 . C10 . 1.370 yes
C9 . H91 . 0.944 no
C10 . C11 . 1.419 yes
C10 . H101 . 0.917 no
C11 . C12 . 1.435 yes
C12 . C13 . 1.489 yes
C13 . C14 . 1.428 yes
C13 . C22 . 1.380 yes
C14 . C15 . 1.412 yes
C14 . C19 . 1.430 yes
C15 . C16 . 1.369 yes
C15 . H151 . 0.925 no
C16 . C17 . 1.413 yes
C16 . H161 . 0.931 no
C17 . C18 . 1.346 yes
C17 . H171 . 0.943 no
C18 . C19 . 1.402 yes
C18 . H181 . 0.962 no
C19 . C20 . 1.406 yes
C20 . C21 . 1.346 yes
C20 . H201 . 0.949 no
C21 . C22 . 1.414 yes
C21 . H211 . 0.940 no
C22 . O23 . 1.377 yes
N24 . C25 . 1.490 yes
N24 . C26 . 1.501 yes
C25 . C29 . 1.527 yes
C25 . C43 . 1.537 yes
C25 . H251 . 0.986 no
C26 . C27 . 1.520 yes
C26 . C28 . 1.525 yes
C26 . H261 . 0.981 no
C27 . H273 . 0.958 no
C27 . H271 . 0.977 no
C27 . H272 . 0.963 no
C28 . H281 . 0.944 no
C28 . H282 . 0.933 no
C28 . H283 . 0.972 no
C29 . C30 . 1.369 yes
C29 . C38 . 1.431 yes
C30 . C31 . 1.409 yes
C30 . H301 . 0.935 no
C31 . C32 . 1.361 yes
C31 . H311 . 0.939 no
C32 . C33 . 1.406 yes
C32 . H321 . 0.950 no
C33 . C34 . 1.422 yes
C33 . C38 . 1.425 yes
C34 . C35 . 1.357 yes
C34 . H341 . 0.927 no
C35 . C36 . 1.399 yes
C35 . H351 . 0.970 no
C36 . C37 . 1.374 yes
C36 . H361 . 0.950 no
C37 . C38 . 1.421 yes
C37 . H371 . 0.958 no
C43 . C44 . 1.404 yes
C43 . C48 . 1.392 yes
C44 . C45 . 1.398 yes
C44 . C49 . 1.502 yes
C45 . C46 . 1.385 yes
C45 . H451 . 0.947 no
C46 . C47 . 1.384 yes
C46 . C50 . 1.519 yes
C47 . C48 . 1.392 yes
C47 . H471 . 0.932 no
C48 . H481 . 0.938 no
C49 . H492 . 0.948 no
C49 . H493 . 0.981 no
C49 . H491 . 0.961 no
C50 . H503 . 0.948 no
C50 . H501 . 0.979 no
C50 . H502 . 0.955 no
C61 . Cl62 . 1.748 yes
C61 . Cl63 . 1.736 yes
C61 . H611 . 0.998 no
C61 . H612 . 0.957 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
O2 . P1 . O23 . 97.30 yes
O2 . P1 . N24 . 96.26 yes
O23 . P1 . N24 . 107.03 yes
P1 . O2 . C3 . 116.89 yes
O2 . C3 . C4 . 117.35 yes
O2 . C3 . C12 . 120.17 yes
C4 . C3 . C12 . 122.45 yes
C3 . C4 . C5 . 119.90 yes
C3 . C4 . H41 . 120.2 no
C5 . C4 . H41 . 119.9 no
C4 . C5 . C6 . 120.33 yes
C4 . C5 . H51 . 121.7 no
C6 . C5 . H51 . 118.0 no
C5 . C6 . C7 . 121.60 yes
C5 . C6 . C11 . 119.20 yes
C7 . C6 . C11 . 119.18 yes
C6 . C7 . C8 . 121.45 yes
C6 . C7 . H71 . 116.8 no
C8 . C7 . H71 . 121.7 no
C7 . C8 . C9 . 119.72 yes
C7 . C8 . H81 . 120.0 no
C9 . C8 . H81 . 120.2 no
C8 . C9 . C10 . 120.47 yes
C8 . C9 . H91 . 120.5 no
C10 . C9 . H91 . 119.1 no
C9 . C10 . C11 . 121.31 yes
C9 . C10 . H101 . 119.5 no
C11 . C10 . H101 . 119.2 no
C6 . C11 . C10 . 117.84 yes
C6 . C11 . C12 . 120.11 yes
C10 . C11 . C12 . 122.01 yes
C11 . C12 . C3 . 117.79 yes
C11 . C12 . C13 . 122.98 yes
C3 . C12 . C13 . 119.17 yes
C12 . C13 . C14 . 122.68 yes
C12 . C13 . C22 . 119.03 yes
C14 . C13 . C22 . 118.28 yes
C13 . C14 . C15 . 122.90 yes
C13 . C14 . C19 . 119.06 yes
C15 . C14 . C19 . 118.03 yes
C14 . C15 . C16 . 120.30 yes
C14 . C15 . H151 . 120.4 no
C16 . C15 . H151 . 119.3 no
C15 . C16 . C17 . 120.81 yes
C15 . C16 . H161 . 119.9 no
C17 . C16 . H161 . 119.1 no
C16 . C17 . C18 . 120.05 yes
C16 . C17 . H171 . 119.6 no
C18 . C17 . H171 . 120.4 no
C17 . C18 . C19 . 121.05 yes
C17 . C18 . H181 . 118.7 no
C19 . C18 . H181 . 120.2 no
C14 . C19 . C18 . 119.63 yes
C14 . C19 . C20 . 119.33 yes
C18 . C19 . C20 . 121.03 yes
C19 . C20 . C21 . 121.43 yes
C19 . C20 . H201 . 118.4 no
C21 . C20 . H201 . 120.1 no
C20 . C21 . C22 . 119.61 yes
C20 . C21 . H211 . 121.7 no
C22 . C21 . H211 . 118.7 no
C21 . C22 . C13 . 122.12 yes
C21 . C22 . O23 . 116.77 yes
C13 . C22 . O23 . 121.08 yes
C22 . O23 . P1 . 123.53 yes
P1 . N24 . C25 . 118.39 yes
P1 . N24 . C26 . 122.19 yes
C25 . N24 . C26 . 117.48 yes
N24 . C25 . C29 . 113.01 yes
N24 . C25 . C43 . 112.37 yes
C29 . C25 . C43 . 110.53 yes
N24 . C25 . H251 . 106.5 no
C29 . C25 . H251 . 106.2 no
C43 . C25 . H251 . 107.8 no
N24 . C26 . C27 . 114.55 yes
N24 . C26 . C28 . 111.15 yes
C27 . C26 . C28 . 110.62 yes
N24 . C26 . H261 . 104.2 no
C27 . C26 . H261 . 107.5 no
C28 . C26 . H261 . 108.4 no
C26 . C27 . H273 . 109.0 no
C26 . C27 . H271 . 112.4 no
H273 . C27 . H271 . 107.3 no
C26 . C27 . H272 . 109.3 no
H273 . C27 . H272 . 109.5 no
H271 . C27 . H272 . 109.3 no
C26 . C28 . H281 . 111.1 no
C26 . C28 . H282 . 111.6 no
H281 . C28 . H282 . 107.0 no
C26 . C28 . H283 . 108.5 no
H281 . C28 . H283 . 108.5 no
H282 . C28 . H283 . 110.0 no
C25 . C29 . C30 . 121.37 yes
C25 . C29 . C38 . 119.43 yes
C30 . C29 . C38 . 119.19 yes
C29 . C30 . C31 . 121.53 yes
C29 . C30 . H301 . 121.0 no
C31 . C30 . H301 . 117.4 no
C30 . C31 . C32 . 119.99 yes
C30 . C31 . H311 . 118.3 no
C32 . C31 . H311 . 121.7 no
C31 . C32 . C33 . 120.98 yes
C31 . C32 . H321 . 120.3 no
C33 . C32 . H321 . 118.7 no
C32 . C33 . C34 . 121.43 yes
C32 . C33 . C38 . 119.29 yes
C34 . C33 . C38 . 119.27 yes
C33 . C34 . C35 . 121.29 yes
C33 . C34 . H341 . 118.1 no
C35 . C34 . H341 . 120.6 no
C34 . C35 . C36 . 119.68 yes
C34 . C35 . H351 . 121.7 no
C36 . C35 . H351 . 118.6 no
C35 . C36 . C37 . 121.22 yes
C35 . C36 . H361 . 120.0 no
C37 . C36 . H361 . 118.7 no
C36 . C37 . C38 . 120.69 yes
C36 . C37 . H371 . 119.1 no
C38 . C37 . H371 . 120.2 no
C29 . C38 . C33 . 118.91 yes
C29 . C38 . C37 . 123.26 yes
C33 . C38 . C37 . 117.81 yes
C25 . C43 . C44 . 120.62 yes
C25 . C43 . C48 . 120.63 yes
C44 . C43 . C48 . 118.73 yes
C43 . C44 . C45 . 118.92 yes
C43 . C44 . C49 . 122.02 yes
C45 . C44 . C49 . 119.03 yes
C44 . C45 . C46 . 122.19 yes
C44 . C45 . H451 . 117.9 no
C46 . C45 . H451 . 119.9 no
C45 . C46 . C47 . 118.44 yes
C45 . C46 . C50 . 120.78 yes
C47 . C46 . C50 . 120.78 yes
C46 . C47 . C48 . 120.45 yes
C46 . C47 . H471 . 120.2 no
C48 . C47 . H471 . 119.2 no
C47 . C48 . C43 . 121.26 yes
C47 . C48 . H481 . 118.3 no
C43 . C48 . H481 . 120.5 no
C44 . C49 . H492 . 109.9 no
C44 . C49 . H493 . 109.4 no
H492 . C49 . H493 . 110.1 no
C44 . C49 . H491 . 108.0 no
H492 . C49 . H491 . 109.3 no
H493 . C49 . H491 . 110.2 no
C46 . C50 . H503 . 110.1 no
C46 . C50 . H501 . 107.0 no
H503 . C50 . H501 . 108.6 no
C46 . C50 . H502 . 113.6 no
H503 . C50 . H502 . 107.8 no
H501 . C50 . H502 . 109.7 no
Cl62 . C61 . Cl63 . 113.91 yes
Cl62 . C61 . H611 . 105.2 no
Cl63 . C61 . H611 . 111.5 no
Cl62 . C61 . H612 . 107.0 no
Cl63 . C61 . H612 . 109.4 no
H611 . C61 . H612 . 109.6 no
