# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1585747'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   19.5805(2)
_cell_length_b                   9.75950(10)
_cell_length_c                   8.96440(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.1581(12)
_cell_angle_gamma                90
_cell_volume                     1668.08(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-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'
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'
B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 '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'
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'


_cell_formula_units_Z            4

# Given Formula = C17 H19 B1 F4 N2 O1 
# Dc =      1.41 Fooo =    736.00 Mu =     10.13 M =    354.15
# Found Formula = C17 H19 B1 F4 N2 O1 
# Dc =      1.41 FOOO =    736.00 Mu =     10.13 M =    354.15

_chemical_formula_sum            'C17 H19 B F4 N2 O'
_chemical_formula_moiety         'C17 H19 N2 O, B F4'
_chemical_compound_source        ?
_chemical_formula_weight         354.15


_cell_measurement_reflns_used    10122
_cell_measurement_theta_min      5
_cell_measurement_theta_max      79
_cell_measurement_temperature    160

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.014
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_max          0.262

_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    1.013

# Sheldrick geometric approximatio 0.79 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.21
_exptl_absorpt_correction_T_max  0.99
_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      160
_diffrn_reflns_number            18232
_reflns_number_total             3411
_diffrn_reflns_av_R_equivalents  0.033
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3411 
# Theoretical number of reflections is about 6823 


_diffrn_reflns_theta_min         4.638
_diffrn_reflns_theta_max         74.504
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        74.504
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -24
_reflns_limit_h_max              23
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   2.60
_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         -0.21
_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         3411
_refine_ls_number_restraints     0
_refine_ls_number_parameters     226
_oxford_refine_ls_R_factor_ref   0.0399
_refine_ls_wR_factor_ref         0.0971
_refine_ls_goodness_of_fit_ref   0.9896
_refine_ls_shift/su_max          0.0012482
_refine_ls_shift/su_mean         0.0000583


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3411
_refine_ls_R_factor_all          0.0399
_refine_ls_wR_factor_all         0.0971

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3088
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_gt          0.0942

# 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 .


_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 + 0.65P] 
 ,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 0.91369(6) 0.51283(12) 0.66471(13) 0.0317 1.0000 Uani . . . . . .
C2 C 0.84329(7) 0.57722(14) 0.65159(14) 0.0283 1.0000 Uani . . . . . .
C3 C 0.82448(7) 0.66542(13) 0.50715(14) 0.0259 1.0000 Uani . . . . . .
C4 C 0.81877(6) 0.58092(12) 0.36546(13) 0.0228 1.0000 Uani . . . . . .
C5 C 0.86937(6) 0.56090(13) 0.28403(14) 0.0261 1.0000 Uani . . . . . .
N6 N 0.84667(5) 0.46781(12) 0.16948(12) 0.0274 1.0000 Uani . . . . . .
C7 C 0.78069(6) 0.42318(13) 0.17596(13) 0.0241 1.0000 Uani . . . . . .
C8 C 0.76089(6) 0.49384(12) 0.29649(13) 0.0220 1.0000 Uani . . . . . .
C9 C 0.73628(7) 0.32769(14) 0.08622(15) 0.0290 1.0000 Uani . . . . . .
C10 C 0.67098(7) 0.30841(13) 0.11602(15) 0.0292 1.0000 Uani . . . . . .
C11 C 0.64921(6) 0.38274(13) 0.23231(14) 0.0250 1.0000 Uani . . . . . .
C12 C 0.69355(6) 0.47415(12) 0.32448(13) 0.0231 1.0000 Uani . . . . . .
O13 O 0.58130(5) 0.35634(10) 0.24322(11) 0.0310 1.0000 Uani . . . . . .
C14 C 0.55186(6) 0.44979(13) 0.33564(15) 0.0266 1.0000 Uani . . . . . .
C15 C 0.47689(6) 0.40842(13) 0.32416(14) 0.0253 1.0000 Uani . . . . . .
C16 C 0.42223(7) 0.48250(15) 0.23453(16) 0.0326 1.0000 Uani . . . . . .
C17 C 0.35304(7) 0.44272(17) 0.22315(17) 0.0375 1.0000 Uani . . . . . .
C18 C 0.33833(7) 0.32792(16) 0.30064(17) 0.0351 1.0000 Uani . . . . . .
C19 C 0.39250(8) 0.25440(15) 0.39224(17) 0.0342 1.0000 Uani . . . . . .
C20 C 0.46149(7) 0.29487(13) 0.40508(15) 0.0294 1.0000 Uani . . . . . .
B21 B 1.02402(8) 0.79114(14) 0.50844(16) 0.0246 1.0000 Uani . . . . . .
F22 F 1.01528(5) 0.81325(10) 0.35254(9) 0.0446 1.0000 Uani . . . . . .
F23 F 0.97431(5) 0.86118(9) 0.56443(12) 0.0446 1.0000 Uani . . . . . .
F24 F 1.09063(4) 0.83679(9) 0.58228(9) 0.0368 1.0000 Uani . . . . . .
F25 F 1.01832(4) 0.65077(8) 0.53260(9) 0.0340 1.0000 Uani . . . . . .
H81 H 0.6798 0.5218 0.4045 0.0286 1.0000 Uiso R . . . . .
H121 H 0.9149 0.6018 0.2992 0.0302 1.0000 Uiso R . . . . .
H141 H 0.8605 0.7361 0.5130 0.0307 1.0000 Uiso R . . . . .
H142 H 0.7788 0.7099 0.5074 0.0308 1.0000 Uiso R . . . . .
H151 H 0.8452 0.6315 0.7425 0.0345 1.0000 Uiso R . . . . .
H152 H 0.8088 0.5032 0.6479 0.0338 1.0000 Uiso R . . . . .
H171 H 0.7498 0.2815 0.0061 0.0342 1.0000 Uiso R . . . . .
H181 H 0.6394 0.2480 0.0549 0.0346 1.0000 Uiso R . . . . .
H191 H 0.5779 0.4441 0.4425 0.0302 1.0000 Uiso R . . . . .
H192 H 0.5548 0.5431 0.2978 0.0319 1.0000 Uiso R . . . . .
H211 H 0.4993 0.2458 0.4698 0.0356 1.0000 Uiso R . . . . .
H221 H 0.3830 0.1762 0.4469 0.0421 1.0000 Uiso R . . . . .
H231 H 0.2906 0.2998 0.2908 0.0422 1.0000 Uiso R . . . . .
H241 H 0.3161 0.4926 0.1598 0.0463 1.0000 Uiso R . . . . .
H251 H 0.4330 0.5583 0.1795 0.0401 1.0000 Uiso R . . . . .
H161 H 0.9166 0.4711 0.5732 0.0479 1.0000 Uiso R . . . . .
H162 H 0.9485 0.5771 0.6866 0.0480 1.0000 Uiso R . . . . .
H163 H 0.9213 0.4505 0.7421 0.0483 1.0000 Uiso R . . . . .
H1 H 0.8713 0.4370 0.1093 0.0334 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.06(14)
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 . 1.4951(17) yes
N1 . H161 . 0.928 no
N1 . H162 . 0.914 no
N1 . H163 . 0.909 no
C2 . C3 . 1.5284(18) yes
C2 . H151 . 0.966 no
C2 . H152 . 0.985 no
C3 . C4 . 1.4971(17) yes
C3 . H141 . 0.980 no
C3 . H142 . 0.995 no
C4 . C5 . 1.3717(17) yes
C4 . C8 . 1.4387(16) yes
C5 . N6 . 1.3674(17) yes
C5 . H121 . 0.958 no
N6 . C7 . 1.3771(16) yes
N6 . H1 . 0.855 no
C7 . C8 . 1.4086(16) yes
C7 . C9 . 1.3976(18) yes
C8 . C12 . 1.4104(16) yes
C9 . C10 . 1.3772(18) yes
C9 . H171 . 0.936 no
C10 . C11 . 1.4132(17) yes
C10 . H181 . 0.936 no
C11 . C12 . 1.3805(17) yes
C11 . O13 . 1.3796(14) yes
C12 . H81 . 0.944 no
O13 . C14 . 1.4380(15) yes
C14 . C15 . 1.5032(16) yes
C14 . H191 . 0.979 no
C14 . H192 . 0.978 no
C15 . C16 . 1.3864(18) yes
C15 . C20 . 1.3946(18) yes
C16 . C17 . 1.3907(19) yes
C16 . H251 . 0.939 no
C17 . C18 . 1.383(2) yes
C17 . H241 . 0.946 no
C18 . C19 . 1.385(2) yes
C18 . H231 . 0.959 no
C19 . C20 . 1.3867(19) yes
C19 . H221 . 0.948 no
C20 . H211 . 0.958 no
B21 . F22 . 1.3857(16) yes
B21 . F23 . 1.3744(16) yes
B21 . F24 . 1.3945(16) yes
B21 . F25 . 1.3954(16) 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 . H161 . 110.8 no
C2 . N1 . H162 . 110.9 no
H161 . N1 . H162 . 107.3 no
C2 . N1 . H163 . 109.2 no
H161 . N1 . H163 . 110.4 no
H162 . N1 . H163 . 108.1 no
N1 . C2 . C3 . 110.09(10) yes
N1 . C2 . H151 . 107.8 no
C3 . C2 . H151 . 111.2 no
N1 . C2 . H152 . 107.9 no
C3 . C2 . H152 . 110.7 no
H151 . C2 . H152 . 109.0 no
C2 . C3 . C4 . 111.44(10) yes
C2 . C3 . H141 . 108.6 no
C4 . C3 . H141 . 110.3 no
C2 . C3 . H142 . 106.7 no
C4 . C3 . H142 . 110.4 no
H141 . C3 . H142 . 109.2 no
C3 . C4 . C5 . 127.34(11) yes
C3 . C4 . C8 . 126.11(11) yes
C5 . C4 . C8 . 106.31(11) yes
C4 . C5 . N6 . 110.10(11) yes
C4 . C5 . H121 . 128.8 no
N6 . C5 . H121 . 121.1 no
C5 . N6 . C7 . 109.04(10) yes
C5 . N6 . H1 . 125.0 no
C7 . N6 . H1 . 125.7 no
N6 . C7 . C8 . 107.59(10) yes
N6 . C7 . C9 . 130.80(11) yes
C8 . C7 . C9 . 121.61(11) yes
C4 . C8 . C7 . 106.94(10) yes
C4 . C8 . C12 . 132.92(11) yes
C7 . C8 . C12 . 120.10(11) yes
C7 . C9 . C10 . 117.58(11) yes
C7 . C9 . H171 . 121.0 no
C10 . C9 . H171 . 121.3 no
C9 . C10 . C11 . 121.48(12) yes
C9 . C10 . H181 . 119.4 no
C11 . C10 . H181 . 119.0 no
C10 . C11 . C12 . 121.26(11) yes
C10 . C11 . O13 . 114.45(11) yes
C12 . C11 . O13 . 124.29(11) yes
C8 . C12 . C11 . 117.89(11) yes
C8 . C12 . H81 . 120.6 no
C11 . C12 . H81 . 121.5 no
C11 . O13 . C14 . 116.21(9) yes
O13 . C14 . C15 . 107.67(10) yes
O13 . C14 . H191 . 109.9 no
C15 . C14 . H191 . 109.6 no
O13 . C14 . H192 . 109.1 no
C15 . C14 . H192 . 111.1 no
H191 . C14 . H192 . 109.4 no
C14 . C15 . C16 . 120.83(12) yes
C14 . C15 . C20 . 120.09(11) yes
C16 . C15 . C20 . 119.08(12) yes
C15 . C16 . C17 . 120.50(13) yes
C15 . C16 . H251 . 118.7 no
C17 . C16 . H251 . 120.8 no
C16 . C17 . C18 . 120.01(13) yes
C16 . C17 . H241 . 119.9 no
C18 . C17 . H241 . 120.0 no
C17 . C18 . C19 . 119.92(13) yes
C17 . C18 . H231 . 119.8 no
C19 . C18 . H231 . 120.3 no
C18 . C19 . C20 . 120.12(13) yes
C18 . C19 . H221 . 120.6 no
C20 . C19 . H221 . 119.2 no
C15 . C20 . C19 . 120.33(13) yes
C15 . C20 . H211 . 118.9 no
C19 . C20 . H211 . 120.8 no
F22 . B21 . F23 . 110.84(12) yes
F22 . B21 . F24 . 108.45(10) yes
F23 . B21 . F24 . 109.35(11) yes
F22 . B21 . F25 . 108.27(11) yes
F23 . B21 . F25 . 110.08(10) yes
F24 . B21 . F25 . 109.83(11) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1585761'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_I                   
;
PROBLEM: D-H Without Acceptor O5 --H51 . Please Check
RESPONSE: There is only one potential hydrogen bond acceptor
in the whole structure (nitrile) and this one is far away from
the hydroxy group.
;
# end Validation Reply Form

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   9.49835(14)
_cell_length_b                   11.89113(17)
_cell_length_c                   22.8675(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2582.79(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'
B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 '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'


_cell_formula_units_Z            4

# Given Formula = C30 H35 B1 N2 O1 
# Dc =      1.16 Fooo =    968.00 Mu =      5.28 M =    450.43
# Found Formula = C31 H35 B1 N2 O1 
# Dc =      1.19 FOOO =    992.00 Mu =      5.42 M =    462.44

_chemical_formula_sum            'C31 H35 B1 N2 O1'
_chemical_formula_moiety         'C24 H20 B, C7 H15 N2 O'
_chemical_compound_source        ?
_chemical_formula_weight         462.44


_cell_measurement_reflns_used    13220
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    160

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.093
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_max          0.425

_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.542

# Sheldrick geometric approximatio 0.95 0.95 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.95
_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      160
_diffrn_reflns_number            21298
_reflns_number_total             5254
_diffrn_reflns_av_R_equivalents  0.024
# Number of reflections without Friedels Law is 5254 
# Number of reflections with Friedels Law is 2981 
# Theoretical number of reflections is about 2640 


_diffrn_reflns_theta_min         3.866
_diffrn_reflns_theta_max         74.454
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        74.454
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   2.35
_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         -0.11
_refine_diff_density_max         0.21


# 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         5254
_refine_ls_number_restraints     0
_refine_ls_number_parameters     316
_oxford_refine_ls_R_factor_ref   0.0281
_refine_ls_wR_factor_ref         0.0713
_refine_ls_goodness_of_fit_ref   0.9920
_refine_ls_shift/su_max          0.0016783
_refine_ls_shift/su_mean         0.0003885


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5254
_refine_ls_R_factor_all          0.0281
_refine_ls_wR_factor_all         0.0713

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5101
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_gt          0.0703

_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_abs_structure_details 'Flack (1983), 2273 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    noref #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 + 0.37P] 
 ,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 0.44661(19) 0.33175(13) 0.31927(7) 0.0696 1.0000 Uani . . . . . .
C2 C 0.53411(17) 0.34531(11) 0.35202(6) 0.0441 1.0000 Uani . . . . . .
C3 C 0.64544(14) 0.37212(10) 0.39372(5) 0.0327 1.0000 Uani . . . . . .
C4 C 0.65438(12) 0.49985(9) 0.40405(5) 0.0272 1.0000 Uani . . . . . .
O5 O 0.75302(10) 0.52226(8) 0.44896(4) 0.0374 1.0000 Uani . . . . . .
C6 C 0.70784(12) 0.55766(9) 0.34887(5) 0.0261 1.0000 Uani . . . . . .
N7 N 0.66145(10) 0.67802(8) 0.34031(4) 0.0261 1.0000 Uani . . . . . .
C8 C 0.68748(13) 0.74793(10) 0.39378(5) 0.0313 1.0000 Uani . . . . . .
C9 C 0.74466(15) 0.72568(10) 0.29011(5) 0.0363 1.0000 Uani . . . . . .
C10 C 0.50800(13) 0.68303(11) 0.32459(5) 0.0341 1.0000 Uani . . . . . .
B11 B 0.72302(12) 0.53618(9) 0.62890(5) 0.0209 1.0000 Uani . . . . . .
C12 C 0.71834(11) 0.65909(8) 0.59482(4) 0.0223 1.0000 Uani . . . . . .
C13 C 0.60431(13) 0.73266(10) 0.60064(5) 0.0322 1.0000 Uani . . . . . .
C14 C 0.59547(15) 0.83526(11) 0.57140(6) 0.0386 1.0000 Uani . . . . . .
C15 C 0.70381(15) 0.86915(10) 0.53520(5) 0.0370 1.0000 Uani . . . . . .
C16 C 0.81840(14) 0.79890(10) 0.52814(5) 0.0333 1.0000 Uani . . . . . .
C17 C 0.82489(12) 0.69589(9) 0.55704(4) 0.0255 1.0000 Uani . . . . . .
C18 C 0.64046(10) 0.54931(8) 0.69209(4) 0.0216 1.0000 Uani . . . . . .
C19 C 0.65799(12) 0.64428(9) 0.72822(5) 0.0285 1.0000 Uani . . . . . .
C20 C 0.58141(14) 0.65979(10) 0.77953(5) 0.0345 1.0000 Uani . . . . . .
C21 C 0.48361(13) 0.57995(12) 0.79731(5) 0.0365 1.0000 Uani . . . . . .
C22 C 0.46682(12) 0.48383(11) 0.76407(5) 0.0335 1.0000 Uani . . . . . .
C23 C 0.54381(12) 0.46985(10) 0.71255(5) 0.0263 1.0000 Uani . . . . . .
C24 C 0.63992(11) 0.44085(9) 0.58974(4) 0.0222 1.0000 Uani . . . . . .
C25 C 0.52444(12) 0.46725(10) 0.55415(5) 0.0276 1.0000 Uani . . . . . .
C26 C 0.44637(13) 0.38596(12) 0.52442(5) 0.0356 1.0000 Uani . . . . . .
C27 C 0.48072(14) 0.27385(12) 0.52950(5) 0.0377 1.0000 Uani . . . . . .
C28 C 0.59470(15) 0.24367(10) 0.56410(5) 0.0367 1.0000 Uani . . . . . .
C29 C 0.67230(13) 0.32552(9) 0.59331(5) 0.0299 1.0000 Uani . . . . . .
C30 C 0.88809(11) 0.49811(8) 0.63774(4) 0.0222 1.0000 Uani . . . . . .
C31 C 0.96394(12) 0.51177(9) 0.68983(5) 0.0249 1.0000 Uani . . . . . .
C32 C 1.10591(12) 0.48330(10) 0.69518(5) 0.0301 1.0000 Uani . . . . . .
C33 C 1.17847(11) 0.43910(10) 0.64777(6) 0.0318 1.0000 Uani . . . . . .
C34 C 1.10665(12) 0.42406(9) 0.59537(5) 0.0307 1.0000 Uani . . . . . .
C35 C 0.96553(12) 0.45311(9) 0.59102(5) 0.0272 1.0000 Uani . . . . . .
H31 H 0.6237 0.3363 0.4303 0.0399 1.0000 Uiso . . . . . .
H32 H 0.7363 0.3468 0.3785 0.0400 1.0000 Uiso . . . . . .
H41 H 0.5603 0.5283 0.4148 0.0304 1.0000 Uiso . . . . . .
H61 H 0.8125 0.5595 0.3505 0.0307 1.0000 Uiso . . . . . .
H62 H 0.6773 0.5172 0.3134 0.0290 1.0000 Uiso . . . . . .
H83 H 0.6613 0.8248 0.3843 0.0457 1.0000 Uiso . . . . . .
H82 H 0.7874 0.7421 0.4042 0.0463 1.0000 Uiso . . . . . .
H81 H 0.6301 0.7188 0.4268 0.0455 1.0000 Uiso . . . . . .
H91 H 0.7136 0.8022 0.2828 0.0526 1.0000 Uiso . . . . . .
H92 H 0.8462 0.7236 0.3001 0.0513 1.0000 Uiso . . . . . .
H93 H 0.7280 0.6792 0.2548 0.0520 1.0000 Uiso . . . . . .
H101 H 0.4804 0.7607 0.3204 0.0500 1.0000 Uiso . . . . . .
H102 H 0.4521 0.6489 0.3562 0.0496 1.0000 Uiso . . . . . .
H103 H 0.4951 0.6435 0.2873 0.0501 1.0000 Uiso . . . . . .
H131 H 0.5304 0.7113 0.6257 0.0384 1.0000 Uiso . . . . . .
H141 H 0.5159 0.8821 0.5756 0.0461 1.0000 Uiso . . . . . .
H151 H 0.6979 0.9386 0.5154 0.0441 1.0000 Uiso . . . . . .
H161 H 0.8928 0.8185 0.5030 0.0405 1.0000 Uiso . . . . . .
H171 H 0.9051 0.6473 0.5506 0.0303 1.0000 Uiso . . . . . .
H191 H 0.7229 0.7044 0.7161 0.0336 1.0000 Uiso . . . . . .
H201 H 0.5964 0.7275 0.8028 0.0416 1.0000 Uiso . . . . . .
H211 H 0.4295 0.5894 0.8309 0.0444 1.0000 Uiso . . . . . .
H221 H 0.4013 0.4254 0.7767 0.0414 1.0000 Uiso . . . . . .
H231 H 0.5294 0.4018 0.6901 0.0283 1.0000 Uiso . . . . . .
H251 H 0.4985 0.5433 0.5509 0.0342 1.0000 Uiso . . . . . .
H261 H 0.3680 0.4081 0.4999 0.0448 1.0000 Uiso . . . . . .
H271 H 0.4272 0.2180 0.5096 0.0466 1.0000 Uiso . . . . . .
H281 H 0.6212 0.1661 0.5686 0.0434 1.0000 Uiso . . . . . .
H291 H 0.7479 0.3026 0.6173 0.0350 1.0000 Uiso . . . . . .
H311 H 0.9162 0.5417 0.7235 0.0302 1.0000 Uiso . . . . . .
H321 H 1.1513 0.4953 0.7324 0.0372 1.0000 Uiso . . . . . .
H331 H 1.2779 0.4213 0.6508 0.0393 1.0000 Uiso . . . . . .
H341 H 1.1538 0.3926 0.5613 0.0365 1.0000 Uiso . . . . . .
H351 H 0.9191 0.4413 0.5531 0.0324 1.0000 Uiso . . . . . .
H51 H 0.7175 0.5079 0.4824 0.0575 1.0000 Uiso . . . . . .

_refine_ls_extinction_coef       74.265
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          5.89(7)
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 . 1.130(2) yes
C2 . C3 . 1.4591(19) yes
C3 . C4 . 1.5394(16) yes
C3 . H31 . 0.961 no
C3 . H32 . 0.978 no
C4 . O5 . 1.4154(14) yes
C4 . C6 . 1.5240(14) yes
C4 . H41 . 0.987 no
O5 . H51 . 0.853 no
C6 . N7 . 1.5103(14) yes
C6 . H61 . 0.995 no
C6 . H62 . 0.986 no
N7 . C8 . 1.4990(14) yes
N7 . C9 . 1.5047(15) yes
N7 . C10 . 1.5024(15) yes
C8 . H83 . 0.972 no
C8 . H82 . 0.981 no
C8 . H81 . 0.994 no
C9 . H91 . 0.971 no
C9 . H92 . 0.992 no
C9 . H93 . 0.991 no
C10 . H101 . 0.965 no
C10 . H102 . 0.985 no
C10 . H103 . 0.981 no
B11 . C12 . 1.6569(15) yes
B11 . C18 . 1.6515(15) yes
B11 . C24 . 1.6461(15) yes
B11 . C30 . 1.6444(15) yes
C12 . C13 . 1.3986(16) yes
C12 . C17 . 1.4007(15) yes
C13 . C14 . 1.3937(17) yes
C13 . H131 . 0.942 no
C14 . C15 . 1.381(2) yes
C14 . H141 . 0.944 no
C15 . C16 . 1.382(2) yes
C15 . H151 . 0.943 no
C16 . C17 . 1.3931(16) yes
C16 . H161 . 0.941 no
C17 . H171 . 0.967 no
C18 . C19 . 1.4091(15) yes
C18 . C23 . 1.3980(15) yes
C19 . C20 . 1.3929(17) yes
C19 . H191 . 0.984 no
C20 . C21 . 1.389(2) yes
C20 . H201 . 0.974 no
C21 . C22 . 1.382(2) yes
C21 . H211 . 0.931 no
C22 . C23 . 1.3966(16) yes
C22 . H221 . 0.976 no
C23 . H231 . 0.969 no
C24 . C25 . 1.4015(15) yes
C24 . C29 . 1.4079(15) yes
C25 . C26 . 1.3951(17) yes
C25 . H251 . 0.940 no
C26 . C27 . 1.377(2) yes
C26 . H261 . 0.967 no
C27 . C28 . 1.388(2) yes
C27 . H271 . 0.952 no
C28 . C29 . 1.3916(17) yes
C28 . H281 . 0.961 no
C29 . H291 . 0.944 no
C30 . C31 . 1.4015(15) yes
C30 . C35 . 1.4030(15) yes
C31 . C32 . 1.3957(16) yes
C31 . H311 . 0.962 no
C32 . C33 . 1.3880(18) yes
C32 . H321 . 0.965 no
C33 . C34 . 1.3903(18) yes
C33 . H331 . 0.971 no
C34 . C35 . 1.3878(16) yes
C34 . H341 . 0.972 no
C35 . H351 . 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
N1 . C2 . C3 . 175.57(16) yes
C2 . C3 . C4 . 110.85(11) yes
C2 . C3 . H31 . 108.4 no
C4 . C3 . H31 . 108.4 no
C2 . C3 . H32 . 109.8 no
C4 . C3 . H32 . 108.0 no
H31 . C3 . H32 . 111.3 no
C3 . C4 . O5 . 109.49(9) yes
C3 . C4 . C6 . 109.65(9) yes
O5 . C4 . C6 . 107.17(9) yes
C3 . C4 . H41 . 109.0 no
O5 . C4 . H41 . 110.8 no
C6 . C4 . H41 . 110.7 no
C4 . O5 . H51 . 110.5 no
C4 . C6 . N7 . 115.95(9) yes
C4 . C6 . H61 . 108.2 no
N7 . C6 . H61 . 106.0 no
C4 . C6 . H62 . 111.3 no
N7 . C6 . H62 . 105.7 no
H61 . C6 . H62 . 109.5 no
C6 . N7 . C8 . 111.82(8) yes
C6 . N7 . C9 . 107.62(8) yes
C8 . N7 . C9 . 109.08(9) yes
C6 . N7 . C10 . 110.59(9) yes
C8 . N7 . C10 . 109.46(9) yes
C9 . N7 . C10 . 108.18(9) yes
N7 . C8 . H83 . 107.3 no
N7 . C8 . H82 . 108.6 no
H83 . C8 . H82 . 111.6 no
N7 . C8 . H81 . 109.6 no
H83 . C8 . H81 . 110.9 no
H82 . C8 . H81 . 108.7 no
N7 . C9 . H91 . 109.0 no
N7 . C9 . H92 . 109.0 no
H91 . C9 . H92 . 111.0 no
N7 . C9 . H93 . 109.1 no
H91 . C9 . H93 . 109.5 no
H92 . C9 . H93 . 109.2 no
N7 . C10 . H101 . 109.0 no
N7 . C10 . H102 . 109.3 no
H101 . C10 . H102 . 108.8 no
N7 . C10 . H103 . 108.1 no
H101 . C10 . H103 . 109.7 no
H102 . C10 . H103 . 112.0 no
C12 . B11 . C18 . 108.39(8) yes
C12 . B11 . C24 . 109.80(8) yes
C18 . B11 . C24 . 108.26(8) yes
C12 . B11 . C30 . 109.04(8) yes
C18 . B11 . C30 . 111.79(8) yes
C24 . B11 . C30 . 109.54(8) yes
B11 . C12 . C13 . 121.85(9) yes
B11 . C12 . C17 . 123.11(9) yes
C13 . C12 . C17 . 115.01(9) yes
C12 . C13 . C14 . 123.26(11) yes
C12 . C13 . H131 . 117.8 no
C14 . C13 . H131 . 118.9 no
C13 . C14 . C15 . 119.88(12) yes
C13 . C14 . H141 . 121.0 no
C15 . C14 . H141 . 119.1 no
C14 . C15 . C16 . 118.73(11) yes
C14 . C15 . H151 . 119.9 no
C16 . C15 . H151 . 121.4 no
C15 . C16 . C17 . 120.74(11) yes
C15 . C16 . H161 . 120.9 no
C17 . C16 . H161 . 118.3 no
C12 . C17 . C16 . 122.36(11) yes
C12 . C17 . H171 . 118.4 no
C16 . C17 . H171 . 119.2 no
B11 . C18 . C19 . 122.18(9) yes
B11 . C18 . C23 . 122.73(9) yes
C19 . C18 . C23 . 115.03(10) yes
C18 . C19 . C20 . 122.57(11) yes
C18 . C19 . H191 . 119.4 no
C20 . C19 . H191 . 118.0 no
C19 . C20 . C21 . 120.35(11) yes
C19 . C20 . H201 . 119.5 no
C21 . C20 . H201 . 120.2 no
C20 . C21 . C22 . 118.78(10) yes
C20 . C21 . H211 . 121.9 no
C22 . C21 . H211 . 119.4 no
C21 . C22 . C23 . 120.13(11) yes
C21 . C22 . H221 . 120.0 no
C23 . C22 . H221 . 119.9 no
C18 . C23 . C22 . 123.07(11) yes
C18 . C23 . H231 . 118.7 no
C22 . C23 . H231 . 118.2 no
B11 . C24 . C25 . 122.48(9) yes
B11 . C24 . C29 . 122.31(9) yes
C25 . C24 . C29 . 115.01(10) yes
C24 . C25 . C26 . 122.94(11) yes
C24 . C25 . H251 . 117.8 no
C26 . C25 . H251 . 119.3 no
C25 . C26 . C27 . 120.24(12) yes
C25 . C26 . H261 . 120.2 no
C27 . C26 . H261 . 119.6 no
C26 . C27 . C28 . 118.89(11) yes
C26 . C27 . H271 . 120.6 no
C28 . C27 . H271 . 120.5 no
C27 . C28 . C29 . 120.39(12) yes
C27 . C28 . H281 . 120.8 no
C29 . C28 . H281 . 118.8 no
C24 . C29 . C28 . 122.54(11) yes
C24 . C29 . H291 . 118.8 no
C28 . C29 . H291 . 118.7 no
B11 . C30 . C31 . 124.24(9) yes
B11 . C30 . C35 . 120.75(9) yes
C31 . C30 . C35 . 114.95(10) yes
C30 . C31 . C32 . 122.89(11) yes
C30 . C31 . H311 . 118.8 no
C32 . C31 . H311 . 118.4 no
C31 . C32 . C33 . 120.20(11) yes
C31 . C32 . H321 . 118.2 no
C33 . C32 . H321 . 121.6 no
C32 . C33 . C34 . 118.57(10) yes
C32 . C33 . H331 . 120.7 no
C34 . C33 . H331 . 120.7 no
C33 . C34 . C35 . 120.24(11) yes
C33 . C34 . H341 . 120.9 no
C35 . C34 . H341 . 118.9 no
C30 . C35 . C34 . 123.14(11) yes
C30 . C35 . H351 . 119.4 no
C34 . C35 . H351 . 117.5 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
C17 . H171 . C35 . 131 0.97 2.55 3.2746(17) yes
O5 . H51 . C25 . 156 0.85 2.51 3.3057(17) 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_PN050916o_10442_A3_D2_eph_I
_database_code_depnum_ccdc_archive 'CCDC 1585759'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 I N O'
_chemical_formula_weight         293.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.40542(18)
_cell_length_b                   6.94898(18)
_cell_length_c                   16.0701(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.864(3)
_cell_angle_gamma                90
_cell_volume                     600.47(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    4194
_cell_measurement_theta_min      5.513
_cell_measurement_theta_max      73.415

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    20.679
_shelx_estimated_absorpt_T_min   0.079
_shelx_estimated_absorpt_T_max   0.804
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.215
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7652
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.535
_diffrn_reflns_theta_max         74.157
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             2282
_reflns_number_gt                2164
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.898
_reflns_Friedel_fraction_full    0.924

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Rigaku, 2015)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku, 2015)'
_computing_data_reduction        'CrysAlis PRO (Rigaku, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0298P)²+0.7076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 901 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(10)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2282
_refine_ls_number_parameters     121
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6870(14) 1.1846(9) 0.7363(4) 0.0257(14) Uani 1 1 d . . . . .
H1 H 0.6032 1.0924 0.6948 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5505(16) 1.3767(10) 0.7279(4) 0.0294(15) Uani 1 1 d . . . . .
H2 H 0.3717 1.3551 0.7361 0.035 Uiso 1 1 calc R U . . .
C3 C 0.657(2) 1.5292(11) 0.7900(5) 0.045(2) Uani 1 1 d . . . . .
H3A H 0.6205 1.4941 0.8465 0.067 Uiso 1 1 calc R U . . .
H3B H 0.5822 1.6543 0.7748 0.067 Uiso 1 1 calc R U . . .
H3C H 0.8378 1.5370 0.7885 0.067 Uiso 1 1 calc R U . . .
C4 C 0.4752(17) 1.3307(11) 0.5702(4) 0.044(2) Uani 1 1 d . . . . .
H4C H 0.4660 1.4038 0.5178 0.066 Uiso 1 1 calc R U . . .
H4B H 0.3098 1.2814 0.5786 0.066 Uiso 1 1 calc R U . . .
H4A H 0.5906 1.2226 0.5673 0.066 Uiso 1 1 calc R U . . .
C5 C 0.6804(15) 1.1010(10) 0.8235(4) 0.0280(15) Uani 1 1 d . . . . .
C6 C 0.4752(14) 0.9971(9) 0.8412(4) 0.0317(14) Uani 1 1 d . . . . .
H6 H 0.3412 0.9794 0.7988 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4608(16) 0.9181(10) 0.9197(5) 0.0401(17) Uani 1 1 d . . . . .
H7 H 0.3175 0.8478 0.9313 0.048 Uiso 1 1 calc R U . . .
C8 C 0.6578(17) 0.9425(12) 0.9811(5) 0.045(2) Uani 1 1 d . . . . .
H8 H 0.6516 0.8857 1.0346 0.054 Uiso 1 1 calc R U . . .
C9 C 0.8612(16) 1.0481(12) 0.9649(4) 0.0423(18) Uani 1 1 d . . . . .
H9 H 0.9938 1.0670 1.0077 0.051 Uiso 1 1 calc R U . . .
C10 C 0.8742(14) 1.1280(11) 0.8858(4) 0.0349(16) Uani 1 1 d . . . . .
H10 H 1.0158 1.2009 0.8747 0.042 Uiso 1 1 calc R U . . .
N1 N 0.5656(11) 1.4589(8) 0.6415(3) 0.0303(12) Uani 1 1 d . . . . .
H1A H 0.4757 1.5698 0.6370 0.036 Uiso 1 1 calc R U . . .
H1B H 0.7269 1.4901 0.6364 0.036 Uiso 1 1 calc R U . . .
O1 O 0.9333(9) 1.2201(7) 0.7150(3) 0.0320(10) Uani 1 1 d . . . . .
H1C H 0.9953 1.1169 0.6994 0.048 Uiso 1 1 calc R U . . .
I1 I 1.07602(6) 0.79247(7) 0.61731(2) 0.03336(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.430(9) . ?
C1 C5 1.521(9) . ?
C1 C2 1.524(8) . ?
C1 H1 1.0000 . ?
C2 N1 1.511(9) . ?
C2 C3 1.528(11) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N1 1.494(9) . ?
C4 H4C 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4A 0.9800 . ?
C5 C6 1.377(11) . ?
C5 C10 1.386(10) . ?
C6 C7 1.385(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.368(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(10) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
O1 H1C 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C5 113.4(6) . . ?
O1 C1 C2 106.4(5) . . ?
C5 C1 C2 111.1(6) . . ?
O1 C1 H1 108.6 . . ?
C5 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
N1 C2 C1 110.0(6) . . ?
N1 C2 C3 106.6(6) . . ?
C1 C2 C3 113.7(6) . . ?
N1 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4C 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4C C4 H4B 109.5 . . ?
N1 C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
C6 C5 C10 119.2(7) . . ?
C6 C5 C1 119.0(7) . . ?
C10 C5 C1 121.8(7) . . ?
C5 C6 C7 121.1(7) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C8 119.3(8) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 120.3(7) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.1(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.0(7) . . ?
C5 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C4 N1 C2 115.8(6) . . ?
C4 N1 H1A 108.3 . . ?
C2 N1 H1A 108.3 . . ?
C4 N1 H1B 108.3 . . ?
C2 N1 H1B 108.3 . . ?
H1A N1 H1B 107.4 . . ?
C1 O1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 54.7(7) . . . . ?
C5 C1 C2 N1 178.5(7) . . . . ?
O1 C1 C2 C3 -64.7(8) . . . . ?
C5 C1 C2 C3 59.1(8) . . . . ?
O1 C1 C5 C6 -156.6(6) . . . . ?
C2 C1 C5 C6 83.6(7) . . . . ?
O1 C1 C5 C10 24.0(9) . . . . ?
C2 C1 C5 C10 -95.7(8) . . . . ?
C10 C5 C6 C7 -0.7(11) . . . . ?
C1 C5 C6 C7 180.0(6) . . . . ?
C5 C6 C7 C8 -0.7(11) . . . . ?
C6 C7 C8 C9 1.8(11) . . . . ?
C7 C8 C9 C10 -1.6(12) . . . . ?
C6 C5 C10 C9 0.9(11) . . . . ?
C1 C5 C10 C9 -179.7(7) . . . . ?
C8 C9 C10 C5 0.2(11) . . . . ?
C1 C2 N1 C4 55.0(8) . . . . ?
C3 C2 N1 C4 178.7(7) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.069



_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_pn181016o_10453_b9_d3_traz_ox_4
_database_code_depnum_ccdc_archive 'CCDC 1585765'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;
_audit_creation_date             2017-12-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H23 Cl N5 O), C2 O4, 10(H2 O)'
_chemical_formula_sum            'C40 H66 Cl2 N10 O16'
_chemical_formula_weight         1013.92
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C40 H60 N10 O16 Cl2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.1489(4)
_cell_length_b                   13.2904(4)
_cell_length_c                   24.5940(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.293(3)
_cell_angle_gamma                90
_cell_volume                     4911.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10679
_cell_measurement_temperature    159.95(10)
_cell_measurement_theta_max      76.4470
_cell_measurement_theta_min      3.2740
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.782
_exptl_absorpt_coefficient_mu    1.850
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2152
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 -1 -1 0.0220
-10 1 1 0.0290
-4 4 13 0.0213
3 -6 -12 0.0316
-3 -6 10 0.0632
3 6 -10 0.0632
2 5 12 0.0210
-2 -5 -12 0.0341
7 -3 9 0.0501
-1 3 -15 0.0511
-4 -1 -14 0.0338

_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
10.0000 -1.0002 -1.0026 -0.1325 -0.9817 0.2677
-10.0000 1.0002 1.0026 0.1325 0.9817 -0.2677
-4.0004 4.0004 12.9998 0.5205 0.1290 -0.8266
3.0003 -6.0004 -11.9997 -0.3416 -0.0347 0.9872
-3.0004 -5.9998 9.9994 0.9085 0.1491 0.2848
3.0004 5.9998 -9.9994 -0.9085 -0.1491 -0.2848
1.9996 5.0003 11.9984 0.3300 -0.4625 -0.8168
-1.9996 -5.0003 -11.9984 -0.3300 0.4625 0.8168
6.9996 -2.9999 8.9970 0.5516 -0.8580 0.1473
-0.9995 2.9997 -14.9980 -0.9516 0.3684 0.1047
-3.9995 -1.0003 -13.9975 -0.6335 0.6768 0.4403

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20149
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.973
_diffrn_reflns_theta_min         3.624
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -18.00   1.00   15.00    --  -41.94 -37.00 -60.00   98
  2  ω     18.00 116.00   1.00   15.00    --   41.94  37.00 150.00   98
  3  ω    -33.00  66.00   1.00   15.00    --   41.94 -37.00 -30.00   99
  4  ω    -30.00  70.00   1.00   15.00    --   41.94 -57.00-150.00  100
  5  ω     86.00 178.00   1.00   60.00    --  112.00  45.00 -60.00   92
  6  ω     84.00 178.00   1.00   60.00    --  112.00  30.00  30.00   94
  7  ω     39.00 138.00   1.00   60.00    --  112.00 -45.00 -60.00   99
  8  ω     86.00 178.00   1.00   60.00    --  112.00  45.00 -90.00   92
  9  ω     86.00 178.00   1.00   60.00    --  112.00  45.00-180.00   92
 10  ω     84.00 178.00   1.00   60.00    --  112.00  30.00  60.00   94
 11  ω     40.00 141.00   1.00   60.00    --  112.00 -60.00 -59.62  101
 12  ω     40.00 141.00   1.00   60.00    --  112.00 -60.00 -89.82  101
 13  ω     36.00 140.00   1.00   60.00    --  112.00 -30.00  90.00  104
 14  ω     86.00 178.00   1.00   60.00    --  112.00  45.00 -30.00   92
 15  ω     14.00  46.00   1.00   15.00    --   41.94  58.00-119.55   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0135329000
_diffrn_orient_matrix_UB_12      -0.0560910000
_diffrn_orient_matrix_UB_13      0.0531340000
_diffrn_orient_matrix_UB_21      -0.1007169000
_diffrn_orient_matrix_UB_22      -0.0063449000
_diffrn_orient_matrix_UB_23      -0.0191201000
_diffrn_orient_matrix_UB_31      0.0138160000
_diffrn_orient_matrix_UB_32      -0.1013044000
_diffrn_orient_matrix_UB_33      -0.0281604000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4562
_reflns_number_total             5113
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5113
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+3.9562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O31-H31A = O31-H31B = O32-H32A = O34-H34B
 0.83 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C5, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,
 H16B), C18(H18A,H18B), C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C21(H21), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41420(13) 0.67145(15) 0.73979(7) 0.0397(4) Uani 1 1 d . . . . .
C4 C 0.52975(18) 0.82287(15) 0.84626(8) 0.0523(5) Uani 1 1 d . . . . .
H4 H 0.5899 0.8392 0.8588 0.063 Uiso 1 1 calc R . . . .
C5 C 0.4622(2) 0.85998(17) 0.87114(9) 0.0622(7) Uani 1 1 d . U . . .
H5 H 0.4756 0.9032 0.9018 0.075 Uiso 1 1 calc R . . . .
C6 C 0.3720(2) 0.8365(2) 0.85293(9) 0.0672(8) Uani 1 1 d . U . . .
H6 H 0.3261 0.8652 0.8710 0.081 Uiso 1 1 calc R . . . .
C7 C 0.35080(16) 0.7739(2) 0.81041(9) 0.0590(6) Uani 1 1 d . . . . .
H7 H 0.2906 0.7571 0.7982 0.071 Uiso 1 1 calc R . . . .
C9 C 0.50720(13) 0.75839(13) 0.80053(7) 0.0361(4) Uani 1 1 d . . . . .
C11 C 0.53229(14) 0.60221(14) 0.68865(7) 0.0397(4) Uani 1 1 d . . . . .
H11A H 0.4886 0.5485 0.6771 0.048 Uiso 1 1 calc R . . . .
H11B H 0.5890 0.5695 0.7034 0.048 Uiso 1 1 calc R . . . .
C12 C 0.54704(12) 0.66524(14) 0.63885(7) 0.0353(4) Uani 1 1 d . . . . .
H12A H 0.5923 0.7176 0.6500 0.042 Uiso 1 1 calc R . . . .
H12B H 0.5701 0.6216 0.6112 0.042 Uiso 1 1 calc R . . . .
C13 C 0.46141(10) 0.71534(12) 0.61335(6) 0.0281(3) Uani 1 1 d . . . . .
H13A H 0.4112 0.6683 0.6151 0.034 Uiso 1 1 calc R . . . .
H13B H 0.4504 0.7758 0.6350 0.034 Uiso 1 1 calc R . . . .
C15 C 0.37934(9) 0.79639(11) 0.53258(6) 0.0262(3) Uani 1 1 d . . . . .
H15A H 0.3728 0.8596 0.5530 0.031 Uiso 1 1 calc R . . . .
H15B H 0.3284 0.7522 0.5376 0.031 Uiso 1 1 calc R . . . .
C16 C 0.37836(10) 0.81978(12) 0.47239(7) 0.0276(3) Uani 1 1 d . . . . .
H16A H 0.3800 0.7561 0.4516 0.033 Uiso 1 1 calc R . . . .
H16B H 0.3225 0.8553 0.4588 0.033 Uiso 1 1 calc R . . . .
C18 C 0.53919(10) 0.83924(12) 0.48657(6) 0.0270(3) Uani 1 1 d . . . . .
H18A H 0.5875 0.8879 0.4827 0.032 Uiso 1 1 calc R . . . .
H18B H 0.5510 0.7775 0.4661 0.032 Uiso 1 1 calc R . . . .
C19 C 0.53968(10) 0.81355(11) 0.54666(6) 0.0262(3) Uani 1 1 d . . . . .
H19A H 0.5966 0.7802 0.5605 0.031 Uiso 1 1 calc R . . . .
H19B H 0.5352 0.8762 0.5679 0.031 Uiso 1 1 calc R . . . .
C20 C 0.45139(10) 0.92938(10) 0.41148(6) 0.0242(3) Uani 1 1 d . . . . .
C21 C 0.52961(10) 0.95005(11) 0.38843(6) 0.0264(3) Uani 1 1 d . . . . .
H21 H 0.5853 0.9252 0.4052 0.032 Uiso 1 1 calc R . . . .
C22 C 0.52481(11) 1.00717(12) 0.34085(7) 0.0294(3) Uani 1 1 d . . . . .
C23 C 0.44574(12) 1.04339(13) 0.31368(7) 0.0342(4) Uani 1 1 d . . . . .
H23 H 0.4444 1.0828 0.2814 0.041 Uiso 1 1 calc R . . . .
C24 C 0.36819(12) 1.01975(13) 0.33565(7) 0.0351(4) Uani 1 1 d . . . . .
H24 H 0.3126 1.0424 0.3176 0.042 Uiso 1 1 calc R . . . .
C25 C 0.37027(11) 0.96394(12) 0.38334(7) 0.0304(3) Uani 1 1 d . . . . .
H25 H 0.3161 0.9487 0.3973 0.036 Uiso 1 1 calc R . . . .
C27 C 0.44885(10) 0.49052(11) 0.49973(6) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.50014(10) 0.66188(11) 0.73172(6) 0.0335(3) Uani 1 1 d . . . . .
N3 N 0.55891(10) 0.71480(11) 0.76855(6) 0.0363(3) Uani 1 1 d . . . . .
N8 N 0.41933(11) 0.73497(13) 0.78501(6) 0.0405(4) Uani 1 1 d . . . . .
N14 N 0.46407(8) 0.74567(9) 0.55480(5) 0.0227(3) Uani 1 1 d . . . . .
H14 H 0.4699(14) 0.6934(17) 0.5354(9) 0.034 Uiso 1 1 d R . . . .
N17 N 0.45435(8) 0.88232(9) 0.46282(5) 0.0245(3) Uani 1 1 d . . . . .
O10 O 0.34649(10) 0.63625(15) 0.71409(6) 0.0600(4) Uani 1 1 d . . . . .
O28 O 0.40324(8) 0.56564(9) 0.50923(6) 0.0401(3) Uani 1 1 d . . . . .
O29 O 0.42088(8) 0.40427(9) 0.48964(6) 0.0395(3) Uani 1 1 d . . . . .
O31 O 0.25790(11) 0.55657(18) 0.56721(8) 0.0723(6) Uani 1 1 d D . . . .
H31A H 0.3048(18) 0.543(3) 0.5507(15) 0.109 Uiso 1 1 d DR . . . .
H31B H 0.2078(17) 0.550(3) 0.5455(14) 0.109 Uiso 1 1 d DR . . . .
O32 O 0.2691(2) 0.45362(17) 0.66803(12) 0.0967(8) Uani 1 1 d D . . . .
H32A H 0.284(3) 0.477(4) 0.6373(13) 0.145 Uiso 1 1 d DR . . . .
H32B H 0.297(3) 0.505(4) 0.694(2) 0.145 Uiso 1 1 d R . . . .
O33 O 0.2500 0.32226(15) 0.5000 0.0478(5) Uani 1 2 d S T P . .
H33 H 0.2896(18) 0.355(2) 0.4954(13) 0.072 Uiso 1 1 d R . . . .
O34 O 0.74416(11) 0.74597(15) 0.81689(8) 0.0607(4) Uani 1 1 d D . . . .
H34A H 0.747(2) 0.811(3) 0.8199(15) 0.091 Uiso 1 1 d R . . . .
H34B H 0.6960(16) 0.731(3) 0.7960(12) 0.091 Uiso 1 1 d DR . . . .
O35 O 0.73344(11) 0.66764(12) 0.92122(7) 0.0498(4) Uani 1 1 d . . . . .
H35A H 0.736(2) 0.691(2) 0.8908(13) 0.075 Uiso 1 1 d R . . . .
H35B H 0.736(2) 0.714(2) 0.9402(13) 0.075 Uiso 1 1 d R . . . .
O36 O 0.7500 0.51256(16) 1.0000 0.0523(5) Uani 1 2 d S T P . .
H36 H 0.747(2) 0.543(2) 0.9717(12) 0.078 Uiso 1 1 d R . . . .
Cl26 Cl 0.62384(3) 1.03765(3) 0.31529(2) 0.04006(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.348(2) . ?
C1 N8 1.391(2) . ?
C1 O10 1.227(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.350(4) . ?
C4 C9 1.421(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.419(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.342(4) . ?
C7 H7 0.9500 . ?
C7 N8 1.379(3) . ?
C9 N3 1.313(2) . ?
C9 N8 1.373(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.523(2) . ?
C11 N2 1.456(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.521(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 N14 1.5010(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.511(2) . ?
C15 N14 1.4908(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 N17 1.4628(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.516(2) . ?
C18 N17 1.4596(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 N14 1.4913(18) . ?
C20 C21 1.404(2) . ?
C20 C25 1.409(2) . ?
C20 N17 1.405(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(2) . ?
C22 C23 1.382(2) . ?
C22 Cl26 1.7463(16) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(2) . ?
C25 H25 0.9500 . ?
C27 C27 1.569(3) 5_666 ?
C27 O28 1.253(2) . ?
C27 O29 1.236(2) . ?
N2 N3 1.380(2) . ?
N14 H14 0.85(2) . ?
O31 H31A 0.879(19) . ?
O31 H31B 0.876(18) . ?
O32 H32A 0.868(19) . ?
O32 H32B 0.99(5) . ?
O33 H33 0.76(3) . ?
O34 H34A 0.86(4) . ?
O34 H34B 0.860(18) . ?
O35 H35A 0.81(3) . ?
O35 H35B 0.77(3) . ?
O36 H36 0.80(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N8 102.61(16) . . ?
O10 C1 N2 130.40(19) . . ?
O10 C1 N8 126.97(19) . . ?
C5 C4 H4 121.3 . . ?
C5 C4 C9 117.3(2) . . ?
C9 C4 H4 121.3 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.1(2) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 121.1 . . ?
C6 C7 N8 117.8(2) . . ?
N8 C7 H7 121.1 . . ?
N3 C9 C4 129.7(2) . . ?
N3 C9 N8 111.37(16) . . ?
N8 C9 C4 118.94(19) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
N2 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
N2 C11 C12 112.47(14) . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.58(15) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N14 C13 C12 112.82(13) . . ?
N14 C13 H13A 109.0 . . ?
N14 C13 H13B 109.0 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
N14 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
N14 C15 C16 110.67(12) . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N17 C16 C15 111.37(12) . . ?
N17 C16 H16A 109.4 . . ?
N17 C16 H16B 109.4 . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
N17 C18 H18A 109.2 . . ?
N17 C18 H18B 109.2 . . ?
N17 C18 C19 111.94(12) . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
N14 C19 C18 110.99(12) . . ?
N14 C19 H19A 109.4 . . ?
N14 C19 H19B 109.4 . . ?
C21 C20 C25 117.78(14) . . ?
C21 C20 N17 121.18(13) . . ?
N17 C20 C25 120.88(14) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.37(14) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 Cl26 118.34(13) . . ?
C23 C22 C21 123.17(15) . . ?
C23 C22 Cl26 118.47(13) . . ?
C22 C23 H23 121.4 . . ?
C22 C23 C24 117.19(16) . . ?
C24 C23 H23 121.4 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.39(16) . . ?
C25 C24 H24 119.3 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.03(15) . . ?
C24 C25 H25 119.5 . . ?
O28 C27 C27 115.97(17) . 5_666 ?
O29 C27 C27 117.64(17) . 5_666 ?
O29 C27 O28 126.39(15) . . ?
C1 N2 C11 125.26(16) . . ?
C1 N2 N3 114.21(15) . . ?
N3 N2 C11 120.52(15) . . ?
C9 N3 N2 103.52(15) . . ?
C7 N8 C1 128.43(19) . . ?
C9 N8 C1 108.28(15) . . ?
C9 N8 C7 123.24(19) . . ?
C13 N14 H14 109.5(14) . . ?
C15 N14 C13 110.26(11) . . ?
C15 N14 C19 108.51(11) . . ?
C15 N14 H14 108.0(14) . . ?
C19 N14 C13 113.94(12) . . ?
C19 N14 H14 106.4(14) . . ?
C18 N17 C16 112.56(12) . . ?
C20 N17 C16 117.49(12) . . ?
C20 N17 C18 117.41(12) . . ?
H31A O31 H31B 113(3) . . ?
H32A O32 H32B 100(4) . . ?
H34A O34 H34B 108(3) . . ?
H35A O35 H35B 105(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N14 H14 O28 0.85(2) 2.04(2) 2.7509(17) 140.6(19) .
N14 H14 O29 0.85(2) 2.25(2) 2.9474(17) 139.0(18) 5_666
O31 H31A O28 0.879(19) 1.93(2) 2.774(2) 159(4) .
O31 H31B O28 0.876(18) 2.03(2) 2.888(2) 168(4) 2_556
O32 H32A O31 0.868(19) 2.02(3) 2.818(4) 152(5) .
O32 H32B O10 0.99(5) 1.94(5) 2.866(3) 155(4) .
O33 H33 O29 0.76(3) 2.12(3) 2.8497(15) 162(3) .
O34 H34A O32 0.86(4) 1.94(4) 2.795(3) 169(3) 4_556
O34 H34B N3 0.860(18) 2.11(2) 2.935(2) 160(3) .
O35 H35A O34 0.81(3) 1.98(3) 2.793(3) 179(4) .
O35 H35B O33 0.77(3) 2.05(3) 2.814(2) 171(3) 3
O36 H36 O35 0.80(3) 2.06(3) 2.818(2) 157(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C9 0.12(19) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C4 C9 N3 N2 179.96(18) . . . . ?
C4 C9 N8 C1 -179.96(16) . . . . ?
C4 C9 N8 C7 2.5(3) . . . . ?
C5 C4 C9 N3 178.08(19) . . . . ?
C5 C4 C9 N8 -1.8(3) . . . . ?
C5 C6 C7 N8 -0.8(3) . . . . ?
C6 C7 N8 C1 -178.2(2) . . . . ?
C6 C7 N8 C9 -1.1(3) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C11 C12 C13 N14 -159.13(14) . . . . ?
C11 N2 N3 C9 -179.95(15) . . . . ?
C12 C11 N2 C1 96.8(2) . . . . ?
C12 C11 N2 N3 -83.15(19) . . . . ?
C12 C13 N14 C15 -178.66(13) . . . . ?
C12 C13 N14 C19 -56.36(17) . . . . ?
C15 C16 N17 C18 53.53(17) . . . . ?
C15 C16 N17 C20 -165.39(12) . . . . ?
C16 C15 N14 C13 -175.48(12) . . . . ?
C16 C15 N14 C19 59.08(15) . . . . ?
C18 C19 N14 C13 178.84(12) . . . . ?
C18 C19 N14 C15 -57.90(15) . . . . ?
C19 C18 N17 C16 -52.50(17) . . . . ?
C19 C18 N17 C20 166.39(12) . . . . ?
C20 C21 C22 C23 -1.7(2) . . . . ?
C20 C21 C22 Cl26 176.44(11) . . . . ?
C21 C20 C25 C24 -2.4(2) . . . . ?
C21 C20 N17 C16 -150.22(14) . . . . ?
C21 C20 N17 C18 -11.0(2) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C22 C23 C24 C25 1.2(3) . . . . ?
C23 C24 C25 C20 0.3(3) . . . . ?
C25 C20 C21 C22 3.1(2) . . . . ?
C25 C20 N17 C16 34.5(2) . . . . ?
C25 C20 N17 C18 173.66(13) . . . . ?
N2 C1 N8 C7 177.35(19) . . . . ?
N2 C1 N8 C9 -0.06(19) . . . . ?
N2 C11 C12 C13 -60.3(2) . . . . ?
N3 C9 N8 C1 0.1(2) . . . . ?
N3 C9 N8 C7 -177.43(18) . . . . ?
N8 C1 N2 C11 -179.96(15) . . . . ?
N8 C1 N2 N3 0.0(2) . . . . ?
N8 C9 N3 N2 -0.15(18) . . . . ?
N14 C15 C16 N17 -57.26(16) . . . . ?
N17 C18 C19 N14 55.13(16) . . . . ?
N17 C20 C21 C22 -172.37(13) . . . . ?
N17 C20 C25 C24 173.04(15) . . . . ?
O10 C1 N2 C11 -1.4(3) . . . . ?
O10 C1 N2 N3 178.5(2) . . . . ?
O10 C1 N8 C7 -1.3(3) . . . . ?
O10 C1 N8 C9 -178.7(2) . . . . ?
Cl26 C22 C23 C24 -178.63(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.636
_oxdiff_exptl_absorpt_empirical_full_min 0.707
####################################################################### 
# 
# 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_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1585748'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   18.7661(5)
_cell_length_b                   8.8339(2)
_cell_length_c                   9.6084(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.318(3)
_cell_angle_gamma                90
_cell_volume                     1567.10(7)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-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'
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'
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'
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 = C17 H19 Cl1 N2 O1 
# Dc =      1.28 Fooo =    640.00 Mu =     21.52 M =    302.80
# Found Formula = C17 H19 Cl1 N2 O1 
# Dc =      1.28 FOOO =    640.00 Mu =     21.52 M =    302.80

_chemical_formula_sum            'C17 H19 Cl N2 O'
_chemical_formula_moiety         'C17 H19 N2 O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         302.80


_cell_measurement_reflns_used    13635
_cell_measurement_theta_min      5
_cell_measurement_theta_max      78
_cell_measurement_temperature    160

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.018
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_max          0.263

_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    2.152

# Sheldrick geometric approximatio 0.73 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.96
_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      160
_diffrn_reflns_number            30743
_reflns_number_total             3187
_diffrn_reflns_av_R_equivalents  0.043
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3187 
# Theoretical number of reflections is about 6409 


_diffrn_reflns_theta_min         4.790
_diffrn_reflns_theta_max         74.494
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        74.494
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -23
_reflns_limit_h_max              23
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   2.96
_oxford_diffrn_Wilson_scale      0.09

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

_refine_diff_density_min         -0.37
_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         3187
_refine_ls_number_restraints     0
_refine_ls_number_parameters     190
_oxford_refine_ls_R_factor_ref   0.0406
_refine_ls_wR_factor_ref         0.0965
_refine_ls_goodness_of_fit_ref   0.9683
_refine_ls_shift/su_max          0.0002011
_refine_ls_shift/su_mean         0.0000245


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3187
_refine_ls_R_factor_all          0.0406
_refine_ls_wR_factor_all         0.0965

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2941
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_gt          0.0949

# 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 .


_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 + 1.06P] 
 ,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
Cl1 Cl 0.04614(2) 0.31157(5) -0.33879(4) 0.0378 1.0000 Uani . . . . . .
O2 O 0.40677(6) 0.36010(14) 0.18747(13) 0.0392 1.0000 Uani . . . . . .
C3 C 0.43842(8) 0.44693(18) 0.30975(17) 0.0327 1.0000 Uani . . . . . .
C4 C 0.51645(8) 0.40148(17) 0.35007(16) 0.0307 1.0000 Uani . . . . . .
C5 C 0.56994(9) 0.4802(2) 0.29780(19) 0.0393 1.0000 Uani . . . . . .
C6 C 0.64211(10) 0.4384(2) 0.3341(2) 0.0455 1.0000 Uani . . . . . .
C7 C 0.66113(10) 0.3161(2) 0.4217(2) 0.0456 1.0000 Uani . . . . . .
C8 C 0.60871(10) 0.2382(2) 0.47639(19) 0.0441 1.0000 Uani . . . . . .
C9 C 0.53655(9) 0.28075(19) 0.44170(17) 0.0364 1.0000 Uani . . . . . .
C10 C 0.33501(8) 0.38869(18) 0.13299(17) 0.0323 1.0000 Uani . . . . . .
C11 C 0.28973(8) 0.47435(17) 0.19955(16) 0.0298 1.0000 Uani . . . . . .
C12 C 0.21791(8) 0.49720(17) 0.12872(16) 0.0293 1.0000 Uani . . . . . .
C13 C 0.19422(8) 0.43341(18) -0.00600(16) 0.0314 1.0000 Uani . . . . . .
N14 N 0.12347(7) 0.47773(16) -0.05135(14) 0.0353 1.0000 Uani . . . . . .
C15 C 0.10229(9) 0.56604(19) 0.05089(18) 0.0360 1.0000 Uani . . . . . .
C16 C 0.15816(8) 0.58222(18) 0.16334(17) 0.0324 1.0000 Uani . . . . . .
C17 C 0.15627(9) 0.66377(19) 0.29911(19) 0.0382 1.0000 Uani . . . . . .
C18 C 0.15278(9) 0.5555(2) 0.42094(18) 0.0380 1.0000 Uani . . . . . .
N19 N 0.08684(7) 0.45903(16) 0.38774(14) 0.0362 1.0000 Uani . . . . . .
C20 C 0.24018(9) 0.34560(19) -0.07240(17) 0.0359 1.0000 Uani . . . . . .
C21 C 0.31012(9) 0.32417(19) -0.00157(18) 0.0373 1.0000 Uani . . . . . .
H31 H 0.4345 0.5558 0.2859 0.0389 1.0000 Uiso R . . . . .
H32 H 0.4125 0.4266 0.3875 0.0388 1.0000 Uiso R . . . . .
H51 H 0.5570 0.5629 0.2372 0.0476 1.0000 Uiso R . . . . .
H61 H 0.6780 0.4912 0.2968 0.0554 1.0000 Uiso R . . . . .
H71 H 0.7095 0.2859 0.4437 0.0545 1.0000 Uiso R . . . . .
H81 H 0.6212 0.1557 0.5356 0.0534 1.0000 Uiso R . . . . .
H91 H 0.5008 0.2305 0.4804 0.0440 1.0000 Uiso R . . . . .
H111 H 0.3062 0.5184 0.2885 0.0355 1.0000 Uiso R . . . . .
H151 H 0.0548 0.6070 0.0403 0.0418 1.0000 Uiso R . . . . .
H171 H 0.1994 0.7246 0.3239 0.0463 1.0000 Uiso R . . . . .
H172 H 0.1141 0.7308 0.2871 0.0459 1.0000 Uiso R . . . . .
H181 H 0.1491 0.6116 0.5057 0.0465 1.0000 Uiso R . . . . .
H182 H 0.1954 0.4885 0.4377 0.0446 1.0000 Uiso R . . . . .
H201 H 0.2248 0.3043 -0.1632 0.0424 1.0000 Uiso R . . . . .
H211 H 0.3427 0.2667 -0.0424 0.0445 1.0000 Uiso R . . . . .
H193 H 0.0890 0.3973 0.3124 0.0550 1.0000 Uiso R . . . . .
H192 H 0.0818 0.4025 0.4635 0.0550 1.0000 Uiso R . . . . .
H141 H 0.0969 0.4500 -0.1296 0.0423 1.0000 Uiso R . . . . .
H191 H 0.0457 0.5168 0.3641 0.0555 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.26(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
O2 . C3 . 1.4393(18) yes
O2 . C10 . 1.3779(18) yes
C3 . C4 . 1.501(2) yes
C3 . H31 . 0.988 no
C3 . H32 . 0.978 no
C4 . C5 . 1.387(2) yes
C4 . C9 . 1.391(2) yes
C5 . C6 . 1.387(2) yes
C5 . H51 . 0.938 no
C6 . C7 . 1.377(3) yes
C6 . H61 . 0.941 no
C7 . C8 . 1.379(3) yes
C7 . H71 . 0.934 no
C8 . C9 . 1.387(2) yes
C8 . H81 . 0.929 no
C9 . H91 . 0.936 no
C10 . C11 . 1.378(2) yes
C10 . C21 . 1.414(2) yes
C11 . C12 . 1.411(2) yes
C11 . H111 . 0.940 no
C12 . C13 . 1.409(2) yes
C12 . C16 . 1.437(2) yes
C13 . N14 . 1.378(2) yes
C13 . C20 . 1.396(2) yes
N14 . C15 . 1.368(2) yes
N14 . H141 . 0.860 no
C15 . C16 . 1.372(2) yes
C15 . H151 . 0.950 no
C16 . C17 . 1.496(2) yes
C17 . C18 . 1.522(2) yes
C17 . H171 . 0.966 no
C17 . H172 . 0.978 no
C18 . N19 . 1.489(2) yes
C18 . H181 . 0.966 no
C18 . H182 . 0.985 no
N19 . H193 . 0.913 no
N19 . H192 . 0.902 no
N19 . H191 . 0.920 no
C20 . C21 . 1.379(2) yes
C20 . H201 . 0.942 no
C21 . H211 . 0.934 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
C3 . O2 . C10 . 116.41(12) yes
O2 . C3 . C4 . 108.01(12) yes
O2 . C3 . H31 . 109.1 no
C4 . C3 . H31 . 110.4 no
O2 . C3 . H32 . 109.7 no
C4 . C3 . H32 . 110.4 no
H31 . C3 . H32 . 109.3 no
C3 . C4 . C5 . 120.54(14) yes
C3 . C4 . C9 . 120.65(15) yes
C5 . C4 . C9 . 118.80(15) yes
C4 . C5 . C6 . 120.84(17) yes
C4 . C5 . H51 . 119.4 no
C6 . C5 . H51 . 119.8 no
C5 . C6 . C7 . 119.85(17) yes
C5 . C6 . H61 . 120.3 no
C7 . C6 . H61 . 119.8 no
C6 . C7 . C8 . 119.98(16) yes
C6 . C7 . H71 . 119.9 no
C8 . C7 . H71 . 120.1 no
C7 . C8 . C9 . 120.36(17) yes
C7 . C8 . H81 . 120.4 no
C9 . C8 . H81 . 119.3 no
C4 . C9 . C8 . 120.14(16) yes
C4 . C9 . H91 . 118.9 no
C8 . C9 . H91 . 121.0 no
O2 . C10 . C11 . 124.49(14) yes
O2 . C10 . C21 . 114.45(14) yes
C11 . C10 . C21 . 121.05(14) yes
C10 . C11 . C12 . 118.02(14) yes
C10 . C11 . H111 . 121.3 no
C12 . C11 . H111 . 120.6 no
C11 . C12 . C13 . 120.18(14) yes
C11 . C12 . C16 . 132.87(14) yes
C13 . C12 . C16 . 106.91(13) yes
C12 . C13 . N14 . 107.72(14) yes
C12 . C13 . C20 . 121.53(14) yes
N14 . C13 . C20 . 130.73(14) yes
C13 . N14 . C15 . 108.81(13) yes
C13 . N14 . H141 . 124.8 no
C15 . N14 . H141 . 126.3 no
N14 . C15 . C16 . 110.21(14) yes
N14 . C15 . H151 . 121.9 no
C16 . C15 . H151 . 127.9 no
C12 . C16 . C15 . 106.33(14) yes
C12 . C16 . C17 . 126.50(14) yes
C15 . C16 . C17 . 127.07(15) yes
C16 . C17 . C18 . 112.26(14) yes
C16 . C17 . H171 . 109.5 no
C18 . C17 . H171 . 108.0 no
C16 . C17 . H172 . 109.5 no
C18 . C17 . H172 . 109.0 no
H171 . C17 . H172 . 108.5 no
C17 . C18 . N19 . 110.09(13) yes
C17 . C18 . H181 . 110.2 no
N19 . C18 . H181 . 107.0 no
C17 . C18 . H182 . 110.9 no
N19 . C18 . H182 . 108.1 no
H181 . C18 . H182 . 110.4 no
C18 . N19 . H193 . 111.0 no
C18 . N19 . H192 . 110.3 no
H193 . N19 . H192 . 109.6 no
C18 . N19 . H191 . 111.4 no
H193 . N19 . H191 . 106.9 no
H192 . N19 . H191 . 107.6 no
C13 . C20 . C21 . 117.51(14) yes
C13 . C20 . H201 . 121.7 no
C21 . C20 . H201 . 120.8 no
C10 . C21 . C20 . 121.70(15) yes
C10 . C21 . H211 . 118.0 no
C20 . C21 . H211 . 120.3 no


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_pn280716o_10444_G9_D2
_database_code_depnum_ccdc_archive 'CCDC 1585763'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H26 Cl N5 O3'
_chemical_formula_weight         407.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.10113(10)
_cell_length_b                   13.6250(2)
_cell_length_c                   20.6821(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.5054(12)
_cell_angle_gamma                90
_cell_volume                     2000.36(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    12805
_cell_measurement_theta_min      3.843
_cell_measurement_theta_max      73.826

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.948
_shelx_estimated_absorpt_T_min   0.612
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73321
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Agilent SuperNova dual radiation CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_reflns_number            29860
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.886
_diffrn_reflns_theta_max         74.266
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4036
_reflns_number_gt                3588
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Rigaku, 2015)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku, 2015)'
_computing_data_reduction        'CrysAlis PRO (Rigaku, 2015)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+0.7726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4036
_refine_ls_number_parameters     337
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1265(3) 0.20633(16) 0.78151(10) 0.0337(4) Uani 0.9 1 d . . P A 1
C4 C -0.0349(5) 0.33698(18) 0.63564(13) 0.0453(6) Uani 0.9 1 d . . P A 1
H4A H 0.0699 0.3458 0.6086 0.054 Uiso 0.9 1 calc R U P A 1
C5 C -0.1973(5) 0.3812(2) 0.62164(15) 0.0476(8) Uani 0.9 1 d . . P A 1
H5A H -0.2089 0.4209 0.5840 0.057 Uiso 0.9 1 calc R U P A 1
C6 C -0.3568(7) 0.3697(3) 0.6630(2) 0.0521(11) Uani 0.9 1 d . . P A 1
H6A H -0.4725 0.4012 0.6519 0.062 Uiso 0.9 1 calc R U P A 1
C7 C -0.3430(4) 0.31488(18) 0.71656(12) 0.0460(6) Uani 0.9 1 d . . P A 1
H7A H -0.4466 0.3077 0.7443 0.055 Uiso 0.9 1 calc R U P A 1
C9 C -0.0189(3) 0.27613(13) 0.69152(10) 0.0345(4) Uani 0.9 1 d . . P A 1
C11 C 0.1629(2) 0.10867(12) 0.80521(8) 0.0336(4) Uani 0.9 1 d . . P A 1
H11A H 0.2275 0.0650 0.7746 0.040 Uiso 0.9 1 calc R U P A 1
H11B H 0.0770 0.0677 0.8308 0.040 Uiso 0.9 1 calc R U P A 1
C12 C 0.3095(2) 0.15523(13) 0.85079(8) 0.0347(4) Uani 0.9 1 d . . P A 1
H12A H 0.3761 0.1030 0.8755 0.042 Uiso 0.9 1 calc R U P A 1
H12B H 0.4036 0.1906 0.8251 0.042 Uiso 0.9 1 calc R U P A 1
C13 C 0.2211(2) 0.22594(13) 0.89735(8) 0.0412(4) Uani 0.9 1 d . . P A 1
H13A H 0.1965 0.2889 0.8748 0.049 Uiso 0.9 1 calc R U P A 1
H13B H 0.0984 0.1991 0.9105 0.049 Uiso 0.9 1 calc R U P A 1
O10 O -0.22708(18) 0.18272(11) 0.82593(7) 0.0458(3) Uani 0.9 1 d . . P A 1
N2 N 0.0526(2) 0.18020(12) 0.76880(8) 0.0309(3) Uani 0.9 1 d . . P A 1
N3 N 0.1236(3) 0.22283(12) 0.71357(8) 0.0349(3) Uani 0.9 1 d . . P A 1
N8 N -0.1731(3) 0.26911(12) 0.73019(10) 0.0344(3) Uani 0.9 1 d . U P A 1
C1B C 0.044(3) 0.2183(14) 0.7419(11) 0.033(3) Uiso 0.1 1 d . . P A 2
C4B C -0.412(4) 0.329(2) 0.7144(14) 0.050(7) Uiso 0.1 1 d . . P A 2
H4B H -0.5293 0.3294 0.7352 0.060 Uiso 0.1 1 calc R U P A 2
C5B C -0.390(5) 0.380(3) 0.6568(17) 0.028(7) Uiso 0.1 1 d . . P A 2
H5B H -0.4904 0.4181 0.6384 0.034 Uiso 0.1 1 calc R U P A 2
C6B C -0.248(4) 0.375(2) 0.6322(15) 0.031(6) Uiso 0.1 1 d . . P A 2
H6B H -0.2410 0.4078 0.5918 0.037 Uiso 0.1 1 calc R U P A 2
C7B C -0.069(4) 0.323(2) 0.6541(15) 0.054(9) Uiso 0.1 1 d . . P A 2
H7B H 0.0459 0.3230 0.6318 0.064 Uiso 0.1 1 calc R U P A 2
C9B C -0.256(3) 0.2772(14) 0.7418(9) 0.034(4) Uiso 0.1 1 d . . P A 2
C11B C -0.003(2) 0.1181(13) 0.8420(8) 0.042(4) Uiso 0.1 1 d . . P A 2
H11C H 0.0940 0.0735 0.8251 0.050 Uiso 0.1 1 calc R U P A 2
H11D H -0.1149 0.0777 0.8515 0.050 Uiso 0.1 1 calc R U P A 2
C12B C 0.073(2) 0.1625(12) 0.9061(8) 0.038(3) Uiso 0.1 1 d . . P A 2
H12C H -0.0301 0.1981 0.9273 0.046 Uiso 0.1 1 calc R U P A 2
H12D H 0.1148 0.1087 0.9352 0.046 Uiso 0.1 1 calc R U P A 2
C13B C 0.2211(2) 0.22594(13) 0.89735(8) 0.0412(4) Uani 0.1 1 d . . P A 2
H13C H 0.1703 0.2892 0.8811 0.049 Uiso 0.1 1 calc R U P A 2
H13D H 0.3024 0.1986 0.8636 0.049 Uiso 0.1 1 calc R U P A 2
N2B N -0.057(3) 0.1890(12) 0.7901(9) 0.032(4) Uiso 0.1 1 d . . P A 2
N3B N -0.246(2) 0.2243(10) 0.7943(7) 0.033(3) Uiso 0.1 1 d . . P A 2
N8B N -0.100(3) 0.2785(12) 0.7105(10) 0.0338(7) Uiso 0.1 1 d . U P A 2
O10B O 0.201(3) 0.2054(15) 0.7265(9) 0.067(6) Uiso 0.1 1 d . . P A 2
C15 C 0.5091(2) 0.29976(12) 0.94055(7) 0.0366(3) Uani 1 1 d . . . . .
H15A H 0.4739 0.3638 0.9211 0.044 Uiso 1 1 calc R U . . .
H15B H 0.5820 0.2625 0.9086 0.044 Uiso 1 1 calc R U . . .
C16 C 0.6297(2) 0.31654(14) 1.00093(8) 0.0396(4) Uani 1 1 d . . . . .
H16A H 0.6745 0.2525 1.0180 0.047 Uiso 1 1 calc R U . . .
H16B H 0.7413 0.3560 0.9899 0.047 Uiso 1 1 calc R U . . .
C18 C 0.3467(2) 0.31902(12) 1.06406(7) 0.0343(3) Uani 1 1 d . . . . .
H18A H 0.2739 0.3597 1.0942 0.041 Uiso 1 1 calc R U . . .
H18B H 0.3717 0.2548 1.0849 0.041 Uiso 1 1 calc R U . . .
C19 C 0.2329(2) 0.30385(13) 1.00214(7) 0.0366(3) Uani 1 1 d . . . . .
H19A H 0.1136 0.2701 1.0119 0.044 Uiso 1 1 calc R U . . .
H19B H 0.2014 0.3684 0.9827 0.044 Uiso 1 1 calc R U . . .
C20 C 0.6247(2) 0.41058(10) 1.10255(7) 0.0298(3) Uani 1 1 d . . . . .
C21 C 0.8056(2) 0.44991(11) 1.09452(8) 0.0335(3) Uani 1 1 d . . . . .
H21A H 0.8671 0.4419 1.0546 0.040 Uiso 1 1 calc R U . . .
C22 C 0.8938(2) 0.50016(11) 1.14471(8) 0.0351(3) Uani 1 1 d . . . . .
C23 C 0.8137(2) 0.51344(12) 1.20396(8) 0.0390(4) Uani 1 1 d . . . . .
H23A H 0.8761 0.5496 1.2374 0.047 Uiso 1 1 calc R U . . .
C24 C 0.6386(2) 0.47185(13) 1.21267(8) 0.0394(4) Uani 1 1 d . . . . .
H24A H 0.5807 0.4787 1.2533 0.047 Uiso 1 1 calc R U . . .
C25 C 0.5455(2) 0.42053(12) 1.16384(7) 0.0343(3) Uani 1 1 d . . . . .
H25A H 0.4265 0.3916 1.1718 0.041 Uiso 1 1 calc R U . . .
N14 N 0.33818(17) 0.24511(9) 0.95573(6) 0.0309(3) Uani 1 1 d . . . . .
N17 N 0.52511(17) 0.36745(10) 1.05095(6) 0.0327(3) Uani 1 1 d . . . . .
O31 O 0.2358(8) 0.0617(3) 1.0052(2) 0.0899(13) Uani 0.5 1 d D . P B 3
H31A H 0.305(7) 0.110(3) 0.995(3) 0.085(18) Uiso 0.5 1 d D . P C 3
H31B H 0.251(15) 0.024(6) 1.039(3) 0.18(4) Uiso 0.5 1 d D . P D 3
O33 O 0.2839(8) -0.0066(4) 1.1198(3) 0.109(2) Uani 0.4 1 d . . P E 3
O32 O 0.4166(5) 0.0574(2) 1.0167(2) 0.0702(9) Uani 0.5 1 d D . P F 4
H32A H 0.447(10) 0.105(3) 0.995(3) 0.105 Uiso 0.5 1 d D U P G 4
H32B H 0.518(6) 0.048(5) 0.999(4) 0.105 Uiso 0.5 1 d D U P H 4
O34 O 0.1311(6) -0.0625(3) 1.0572(2) 0.0934(12) Uani 0.5 1 d . . P I 4
O35 O -0.039(4) -0.0476(18) 1.0039(14) 0.113(8) Uiso 0.1 1 d . . P J 5
Cl26 Cl 1.11528(6) 0.55110(3) 1.13186(2) 0.04918(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O10 1.221(2) . ?
C1 N2 1.353(3) . ?
C1 N8 1.396(3) . ?
C4 C5 1.326(4) . ?
C4 C9 1.424(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.445(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.338(5) . ?
C6 H6A 0.9500 . ?
C7 N8 1.381(3) . ?
C7 H7A 0.9500 . ?
C9 N3 1.317(3) . ?
C9 N8 1.376(3) . ?
C11 N2 1.449(2) . ?
C11 C12 1.524(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.510(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N14 1.4711(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N2 N3 1.388(2) . ?
C1B O10B 1.18(3) . ?
C1B N2B 1.31(3) . ?
C1B N8B 1.45(3) . ?
C4B C5B 1.39(5) . ?
C4B C9B 1.42(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.15(5) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.51(5) . ?
C6B H6B 0.9500 . ?
C7B N8B 1.34(4) . ?
C7B H7B 0.9500 . ?
C9B N8B 1.30(3) . ?
C9B N3B 1.30(3) . ?
C11B N2B 1.49(2) . ?
C11B C12B 1.54(2) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B C13B 1.377(16) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B N14 1.4711(19) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
N2B N3B 1.43(2) . ?
C15 N14 1.465(2) . ?
C15 C16 1.513(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N17 1.4638(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 N17 1.4600(19) . ?
C18 C19 1.510(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N14 1.4691(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 N17 1.3943(19) . ?
C20 C21 1.406(2) . ?
C20 C25 1.407(2) . ?
C21 C22 1.380(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.376(2) . ?
C22 Cl26 1.7461(16) . ?
C23 C24 1.383(2) . ?
C23 H23A 0.9500 . ?
C24 C25 1.382(2) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
O31 H31A 0.85(2) . ?
O31 H31B 0.87(2) . ?
O32 H32A 0.83(2) . ?
O32 H32B 0.82(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O10 C1 N2 130.4(3) . . ?
O10 C1 N8 127.0(2) . . ?
N2 C1 N8 102.63(18) . . ?
C5 C4 C9 119.5(3) . . ?
C5 C4 H4A 120.3 . . ?
C9 C4 H4A 120.3 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 N8 117.8(3) . . ?
C6 C7 H7A 121.1 . . ?
N8 C7 H7A 121.1 . . ?
N3 C9 N8 112.10(17) . . ?
N3 C9 C4 130.2(2) . . ?
N8 C9 C4 117.7(2) . . ?
N2 C11 C12 113.12(14) . . ?
N2 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N2 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 111.79(14) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
N14 C13 C12 113.65(13) . . ?
N14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
N14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C1 N2 N3 114.42(19) . . ?
C1 N2 C11 125.03(19) . . ?
N3 N2 C11 120.41(15) . . ?
C9 N3 N2 102.90(19) . . ?
C9 N8 C7 123.7(2) . . ?
C9 N8 C1 107.95(18) . . ?
C7 N8 C1 128.3(2) . . ?
O10B C1B N2B 135(2) . . ?
O10B C1B N8B 129(3) . . ?
N2B C1B N8B 96.9(18) . . ?
C5B C4B C9B 119(2) . . ?
C5B C4B H4B 120.3 . . ?
C9B C4B H4B 120.3 . . ?
C6B C5B C4B 118(3) . . ?
C6B C5B H5B 121.1 . . ?
C4B C5B H5B 121.1 . . ?
C5B C6B C7B 130(3) . . ?
C5B C6B H6B 115.1 . . ?
C7B C6B H6B 115.1 . . ?
N8B C7B C6B 109(2) . . ?
N8B C7B H7B 125.7 . . ?
C6B C7B H7B 125.7 . . ?
N8B C9B N3B 113(2) . . ?
N8B C9B C4B 117.3(19) . . ?
N3B C9B C4B 129(2) . . ?
N2B C11B C12B 116.3(14) . . ?
N2B C11B H11C 108.2 . . ?
C12B C11B H11C 108.2 . . ?
N2B C11B H11D 108.2 . . ?
C12B C11B H11D 108.2 . . ?
H11C C11B H11D 107.4 . . ?
C13B C12B C11B 112.7(13) . . ?
C13B C12B H12C 109.1 . . ?
C11B C12B H12C 109.1 . . ?
C13B C12B H12D 109.1 . . ?
C11B C12B H12D 109.1 . . ?
H12C C12B H12D 107.8 . . ?
C12B C13B N14 114.9(7) . . ?
C12B C13B H13C 108.5 . . ?
N14 C13B H13C 108.5 . . ?
C12B C13B H13D 108.5 . . ?
N14 C13B H13D 108.5 . . ?
H13C C13B H13D 107.5 . . ?
C1B N2B N3B 118.5(16) . . ?
C1B N2B C11B 128(2) . . ?
N3B N2B C11B 113.5(17) . . ?
C9B N3B N2B 99.7(16) . . ?
C9B N8B C7B 127(2) . . ?
C9B N8B C1B 112(2) . . ?
C7B N8B C1B 121(3) . . ?
N14 C15 C16 110.73(12) . . ?
N14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N17 C16 C15 111.62(13) . . ?
N17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
N17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N17 C18 C19 110.60(12) . . ?
N17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
N14 C19 C18 111.01(12) . . ?
N14 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
N14 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
N17 C20 C21 121.12(13) . . ?
N17 C20 C25 121.57(13) . . ?
C21 C20 C25 117.25(14) . . ?
C22 C21 C20 119.88(14) . . ?
C22 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
C23 C22 C21 123.05(15) . . ?
C23 C22 Cl26 118.56(12) . . ?
C21 C22 Cl26 118.39(12) . . ?
C22 C23 C24 117.13(15) . . ?
C22 C23 H23A 121.4 . . ?
C24 C23 H23A 121.4 . . ?
C25 C24 C23 121.78(15) . . ?
C25 C24 H24A 119.1 . . ?
C23 C24 H24A 119.1 . . ?
C24 C25 C20 120.81(15) . . ?
C24 C25 H25A 119.6 . . ?
C20 C25 H25A 119.6 . . ?
C15 N14 C19 107.56(12) . . ?
C15 N14 C13B 111.58(12) . . ?
C19 N14 C13B 110.30(12) . . ?
C15 N14 C13 111.58(12) . . ?
C19 N14 C13 110.30(12) . . ?
C20 N17 C18 118.26(12) . . ?
C20 N17 C16 118.95(12) . . ?
C18 N17 C16 112.06(12) . . ?
H31A O31 H31B 126(8) . . ?
H32A O32 H32B 69(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 C7 0.7(5) . . . . ?
C5 C6 C7 N8 -1.0(5) . . . . ?
C5 C4 C9 N3 177.3(2) . . . . ?
C5 C4 C9 N8 -2.5(3) . . . . ?
N2 C11 C12 C13 56.5(2) . . . . ?
C11 C12 C13 N14 159.10(14) . . . . ?
O10 C1 N2 N3 -179.31(19) . . . . ?
N8 C1 N2 N3 0.75(19) . . . . ?
O10 C1 N2 C11 5.1(3) . . . . ?
N8 C1 N2 C11 -174.81(14) . . . . ?
C12 C11 N2 C1 -103.45(19) . . . . ?
C12 C11 N2 N3 81.24(18) . . . . ?
N8 C9 N3 N2 0.30(18) . . . . ?
C4 C9 N3 N2 -179.48(19) . . . . ?
C1 N2 N3 C9 -0.68(19) . . . . ?
C11 N2 N3 C9 175.11(14) . . . . ?
N3 C9 N8 C7 -177.52(17) . . . . ?
C4 C9 N8 C7 2.3(3) . . . . ?
N3 C9 N8 C1 0.1(2) . . . . ?
C4 C9 N8 C1 179.94(17) . . . . ?
C6 C7 N8 C9 -0.6(3) . . . . ?
C6 C7 N8 C1 -177.7(3) . . . . ?
O10 C1 N8 C9 179.54(18) . . . . ?
N2 C1 N8 C9 -0.52(18) . . . . ?
O10 C1 N8 C7 -2.9(3) . . . . ?
N2 C1 N8 C7 176.99(18) . . . . ?
C9B C4B C5B C6B 3(5) . . . . ?
C4B C5B C6B C7B -3(6) . . . . ?
C5B C6B C7B N8B 1(5) . . . . ?
C5B C4B C9B N8B -1(4) . . . . ?
C5B C4B C9B N3B -179(2) . . . . ?
N2B C11B C12B C13B -54(2) . . . . ?
C11B C12B C13B N14 -160.9(10) . . . . ?
O10B C1B N2B N3B 177(2) . . . . ?
N8B C1B N2B N3B -1.2(19) . . . . ?
O10B C1B N2B C11B -6(4) . . . . ?
N8B C1B N2B C11B 176.0(16) . . . . ?
C12B C11B N2B C1B 96(2) . . . . ?
C12B C11B N2B N3B -86.4(18) . . . . ?
N8B C9B N3B N2B -1.8(19) . . . . ?
C4B C9B N3B N2B 176(2) . . . . ?
C1B N2B N3B C9B 2(2) . . . . ?
C11B N2B N3B C9B -175.6(14) . . . . ?
N3B C9B N8B C7B 178(2) . . . . ?
C4B C9B N8B C7B -1(3) . . . . ?
N3B C9B N8B C1B 1(2) . . . . ?
C4B C9B N8B C1B -176.9(18) . . . . ?
C6B C7B N8B C9B 1(4) . . . . ?
C6B C7B N8B C1B 176.6(19) . . . . ?
O10B C1B N8B C9B -179(2) . . . . ?
N2B C1B N8B C9B 0(2) . . . . ?
O10B C1B N8B C7B 5(3) . . . . ?
N2B C1B N8B C7B -177(2) . . . . ?
N14 C15 C16 N17 -56.53(19) . . . . ?
N17 C18 C19 N14 58.24(18) . . . . ?
N17 C20 C21 C22 174.00(14) . . . . ?
C25 C20 C21 C22 -3.2(2) . . . . ?
C20 C21 C22 C23 0.8(2) . . . . ?
C20 C21 C22 Cl26 -178.04(11) . . . . ?
C21 C22 C23 C24 1.5(2) . . . . ?
Cl26 C22 C23 C24 -179.74(12) . . . . ?
C22 C23 C24 C25 -1.1(2) . . . . ?
C23 C24 C25 C20 -1.4(3) . . . . ?
N17 C20 C25 C24 -173.67(15) . . . . ?
C21 C20 C25 C24 3.5(2) . . . . ?
C16 C15 N14 C19 60.29(16) . . . . ?
C16 C15 N14 C13B -178.62(13) . . . . ?
C16 C15 N14 C13 -178.62(13) . . . . ?
C18 C19 N14 C15 -61.57(16) . . . . ?
C18 C19 N14 C13B 176.54(14) . . . . ?
C18 C19 N14 C13 176.54(14) . . . . ?
C12B C13B N14 C15 170.7(8) . . . . ?
C12B C13B N14 C19 -69.9(8) . . . . ?
C12 C13 N14 C15 67.89(19) . . . . ?
C12 C13 N14 C19 -172.63(15) . . . . ?
C21 C20 N17 C18 173.72(13) . . . . ?
C25 C20 N17 C18 -9.2(2) . . . . ?
C21 C20 N17 C16 32.0(2) . . . . ?
C25 C20 N17 C16 -150.87(15) . . . . ?
C19 C18 N17 C20 163.17(13) . . . . ?
C19 C18 N17 C16 -52.65(18) . . . . ?
C15 C16 N17 C20 -163.93(13) . . . . ?
C15 C16 N17 C18 52.17(18) . . . . ?

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.040



_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_pn040816o
_database_code_depnum_ccdc_archive 'CCDC 1585760'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H32 N2 O6'
_chemical_formula_weight         420.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   13.5545(2)
_cell_length_b                   5.84781(7)
_cell_length_c                   14.1657(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.071(2)
_cell_angle_gamma                90
_cell_volume                     1054.64(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    10199
_cell_measurement_theta_min      3.593
_cell_measurement_theta_max      34.561

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.568
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Agilent SuperNova dual radiation CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_reflns_number            20898
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.591
_diffrn_reflns_theta_max         35.243
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4451
_reflns_number_gt                4049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Rigaku, 2015)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku, 2015)'
_computing_data_reduction        'CrysAlis PRO (Rigaku, 2015)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.2139P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4451
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18071(9) 0.5342(2) 0.69752(9) 0.01544(19) Uani 1 1 d . . . . .
H1 H 0.1187 0.6052 0.6452 0.019 Uiso 1 1 calc R U . . .
C2 C 0.27540(9) 0.6945(2) 0.71678(9) 0.0156(2) Uani 1 1 d . . . . .
H2 H 0.2596 0.8422 0.7442 0.019 Uiso 1 1 calc R U . . .
C3 C 0.37647(10) 0.5971(3) 0.79058(10) 0.0230(2) Uani 1 1 d . . . . .
H3A H 0.3664 0.5627 0.8544 0.035 Uiso 1 1 calc R U . . .
H3B H 0.4331 0.7093 0.8021 0.035 Uiso 1 1 calc R U . . .
H3C H 0.3951 0.4566 0.7629 0.035 Uiso 1 1 calc R U . . .
C4 C 0.36164(10) 0.9314(2) 0.61833(11) 0.0222(2) Uani 1 1 d . . . . .
H4A H 0.3348 1.0743 0.6364 0.033 Uiso 1 1 calc R U . . .
H4B H 0.3671 0.9465 0.5514 0.033 Uiso 1 1 calc R U . . .
H4C H 0.4312 0.8986 0.6676 0.033 Uiso 1 1 calc R U . . .
C5 C 0.15468(9) 0.5033(2) 0.79280(9) 0.0159(2) Uani 1 1 d . . . . .
C6 C 0.18453(10) 0.3085(2) 0.85224(10) 0.0199(2) Uani 1 1 d . . . . .
H6 H 0.2202 0.1884 0.8322 0.024 Uiso 1 1 calc R U . . .
C7 C 0.16246(10) 0.2885(2) 0.94095(10) 0.0223(2) Uani 1 1 d . . . . .
H7 H 0.1828 0.1546 0.9809 0.027 Uiso 1 1 calc R U . . .
C8 C 0.11098(10) 0.4631(2) 0.97104(10) 0.0221(2) Uani 1 1 d . . . . .
H8 H 0.0970 0.4502 1.0321 0.027 Uiso 1 1 calc R U . . .
C9 C 0.07977(11) 0.6570(2) 0.91171(11) 0.0222(2) Uani 1 1 d . . . . .
H9 H 0.0436 0.7761 0.9319 0.027 Uiso 1 1 calc R U . . .
C10 C 0.10129(10) 0.6778(2) 0.82262(10) 0.0191(2) Uani 1 1 d . . . . .
H10 H 0.0796 0.8107 0.7822 0.023 Uiso 1 1 calc R U . . .
C11 C 0.02070(9) 0.98609(19) 0.45521(9) 0.01400(19) Uani 1 1 d . . . . .
N1 N 0.28826(8) 0.74028(18) 0.61777(8) 0.01553(18) Uani 1 1 d . . . . .
H12 H 0.3104(15) 0.616(4) 0.5967(14) 0.023 Uiso 1 1 d . U . . .
H11 H 0.2233(15) 0.779(4) 0.5728(14) 0.023 Uiso 1 1 d . U . . .
O1 O 0.20585(7) 0.32868(16) 0.65838(8) 0.02046(18) Uani 1 1 d . . . . .
H1A H 0.1539 0.2403 0.6427 0.031 Uiso 1 1 calc R U . . .
O11 O 0.11466(7) 0.92376(16) 0.47297(7) 0.01922(18) Uani 1 1 d . . . . .
O12 O -0.04040(7) 1.05314(17) 0.37237(7) 0.02110(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4133(15) . ?
C1 C5 1.5184(16) . ?
C1 C2 1.5362(16) . ?
C1 H1 1.0000 . ?
C2 N1 1.4957(15) . ?
C2 C3 1.5201(18) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N1 1.4942(16) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.3917(17) . ?
C5 C10 1.3976(16) . ?
C6 C7 1.3930(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3837(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3948(18) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 O12 1.2448(14) . ?
C11 O11 1.2642(13) . ?
C11 C11 1.554(2) 2_556 ?
N1 H12 0.88(2) . ?
N1 H11 0.92(2) . ?
O1 H1A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C5 114.11(10) . . ?
O1 C1 C2 106.81(9) . . ?
C5 C1 C2 110.45(9) . . ?
O1 C1 H1 108.4 . . ?
C5 C1 H1 108.4 . . ?
C2 C1 H1 108.4 . . ?
N1 C2 C3 110.14(10) . . ?
N1 C2 C1 107.58(9) . . ?
C3 C2 C1 113.24(10) . . ?
N1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 119.21(11) . . ?
C6 C5 C1 121.81(10) . . ?
C10 C5 C1 118.97(10) . . ?
C5 C6 C7 120.45(12) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.20(12) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.82(12) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 120.27(12) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 120.04(11) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
O12 C11 O11 125.27(11) . . ?
O12 C11 C11 117.38(11) . 2_556 ?
O11 C11 C11 117.32(12) . 2_556 ?
C4 N1 C2 114.87(10) . . ?
C4 N1 H12 108.5(13) . . ?
C2 N1 H12 109.5(13) . . ?
C4 N1 H11 107.2(13) . . ?
C2 N1 H11 107.6(11) . . ?
H12 N1 H11 109.2(18) . . ?
C1 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 62.30(12) . . . . ?
C5 C1 C2 N1 -173.08(9) . . . . ?
O1 C1 C2 C3 -59.65(13) . . . . ?
C5 C1 C2 C3 64.97(12) . . . . ?
O1 C1 C5 C6 19.03(16) . . . . ?
C2 C1 C5 C6 -101.31(13) . . . . ?
O1 C1 C5 C10 -162.40(11) . . . . ?
C2 C1 C5 C10 77.27(13) . . . . ?
C10 C5 C6 C7 -0.65(18) . . . . ?
C1 C5 C6 C7 177.92(12) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 1.1(2) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C8 C9 C10 C5 -0.1(2) . . . . ?
C6 C5 C10 C9 0.88(18) . . . . ?
C1 C5 C10 C9 -177.73(11) . . . . ?
C3 C2 N1 C4 -68.68(14) . . . . ?
C1 C2 N1 C4 167.47(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H12 O11 0.88(2) 1.99(2) 2.8233(14) 158.4(18) 4_546
N1 H11 O11 0.92(2) 1.86(2) 2.7536(14) 163.5(18) .
O1 H1A O12 0.84 1.84 2.6730(13) 171.5 2_546

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_I_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1585757'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   24.3732(2)
_cell_length_b                   10.40840(10)
_cell_length_c                   9.99320(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.1701(9)
_cell_angle_gamma                90
_cell_volume                     2531.26(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-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
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'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
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'
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'
K 0.3868 1.0657 8.2186 12.7949 7.4398 0.7748 1.0519 213.1870 0.8659 41.6841
1.4228 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C14 H18 F9 K0.50 N3 P0.50 S1 
# Dc =      1.22 Fooo =    948.00 Mu =     28.26 M =    466.40
# Found Formula = C14 H18 F18.00 K1 N3 P2 S1 
# Dc =      1.85 FOOO =   1400.00 Mu =     51.96 M =    703.39

_chemical_formula_sum            'C14 H18 F18 K1 N3 P2 S1'
_chemical_formula_moiety         'F12 K P2, C14 H18 F6 N3 S'
_chemical_compound_source        ?
_chemical_formula_weight         703.39


_cell_measurement_reflns_used    19332
_cell_measurement_theta_min      5
_cell_measurement_theta_max      79
_cell_measurement_temperature    160

_exptl_crystal_description       lath
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.017
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_max          0.109

_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    5.196

# Sheldrick geometric approximatio 0.76 0.92 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.92
_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      160
_diffrn_reflns_number            49106
_reflns_number_total             5098
_diffrn_reflns_av_R_equivalents  0.045
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5098 
# Theoretical number of reflections is about 10354 


_diffrn_reflns_theta_min         3.632
_diffrn_reflns_theta_max         74.496
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        74.33
_diffrn_measured_fraction_theta_full 0.987


_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -30
_reflns_limit_h_max              30
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   2.33
_oxford_diffrn_Wilson_scale      0.27

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

_refine_diff_density_min         -0.48
_refine_diff_density_max         0.84


# 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         5098
_refine_ls_number_restraints     79
_refine_ls_number_parameters     408
_oxford_refine_ls_R_factor_ref   0.0496
_refine_ls_wR_factor_ref         0.1087
_refine_ls_goodness_of_fit_ref   1.0134
_refine_ls_shift/su_max          0.0075753
_refine_ls_shift/su_mean         0.0003175


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5098
_refine_ls_R_factor_all          0.0496
_refine_ls_wR_factor_all         0.1087

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4507
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_gt          0.1053

# 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 .


_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 + 5.35P] 
 ,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
F118 F 0.5198(3) 0.6907(8) 0.1762(8) 0.0620 0.431(12) Uani . U P 2 1 .
F119 F 0.5217(6) 0.5018(11) 0.2533(15) 0.0551 0.431(12) Uani . U P 2 1 .
F120 F 0.4685(3) 0.6401(12) 0.3328(9) 0.0651 0.431(12) Uani . U P 2 1 .
C21 C 0.36450(16) 0.2614(4) 0.0128(4) 0.0487 1.0000 Uani D U . . . .
F22 F 0.3153(2) 0.2479(4) 0.0695(7) 0.0801 0.758(9) Uani . U P 1 1 .
F23 F 0.3563(3) 0.2201(5) -0.1097(4) 0.0842 0.758(9) Uani . U P 1 1 .
F24 F 0.3962(2) 0.1808(3) 0.0808(7) 0.0909 0.758(9) Uani . U P 1 1 .
F123 F 0.3449(9) 0.2216(13) 0.1147(12) 0.0712 0.242(9) Uani D U P 1 2 .
F124 F 0.3275(6) 0.2410(13) -0.0824(17) 0.0617 0.242(9) Uani . U P 1 2 .
F125 F 0.4048(5) 0.1860(10) -0.020(2) 0.0680 0.242(9) Uani . U P 1 2 .
S1 S 0.32526(3) 0.87503(7) 0.01032(7) 0.0300 1.0000 Uani . . . . . .
C2 C 0.33270(10) 0.8112(3) -0.1423(3) 0.0227 1.0000 Uani . . . . . .
N3 N 0.31128(9) 0.8681(2) -0.2538(2) 0.0259 1.0000 Uani . . . . . .
C4 C 0.27468(11) 0.9783(3) -0.2520(3) 0.0259 1.0000 Uani . . . . . .
C5 C 0.21733(11) 0.9304(3) -0.2251(3) 0.0246 1.0000 Uani . . . . . .
N6 N 0.17827(10) 1.0313(2) -0.1781(2) 0.0259 1.0000 Uani . . . . . .
C7 C 0.12240(13) 0.9704(4) -0.1772(4) 0.0454 1.0000 Uani . . . . . .
C8 C 0.19491(16) 1.0754(4) -0.0399(3) 0.0504 1.0000 Uani . . . . . .
C9 C 0.17497(15) 1.1447(3) -0.2701(3) 0.0392 1.0000 Uani . . . . . .
N10 N 0.35995(10) 0.7006(2) -0.1652(2) 0.0273 1.0000 Uani . . . . . .
C11 C 0.38083(11) 0.6130(3) -0.0660(3) 0.0245 1.0000 Uani . . . . . .
C12 C 0.36261(11) 0.4874(3) -0.0725(3) 0.0281 1.0000 Uani . . . . . .
C13 C 0.38398(12) 0.3979(3) 0.0201(3) 0.0308 1.0000 Uani . . . . . .
C14 C 0.42288(12) 0.4340(3) 0.1193(3) 0.0326 1.0000 Uani . . . . . .
C15 C 0.44083(11) 0.5604(3) 0.1235(3) 0.0289 1.0000 Uani . . . . . .
C16 C 0.42063(11) 0.6501(3) 0.0314(3) 0.0261 1.0000 Uani . . . . . .
C17 C 0.48348(14) 0.5981(4) 0.2304(4) 0.0410 1.0000 Uani . . . . . .
F18 F 0.4905(3) 0.7214(5) 0.2412(8) 0.0719 0.569(12) Uani . U P 2 2 .
F19 F 0.4636(2) 0.5686(8) 0.3570(5) 0.0551 0.569(12) Uani . U P 2 2 .
F20 F 0.5274(4) 0.5371(11) 0.2275(11) 0.0640 0.569(12) Uani . U P 2 2 .
P25 P 0.19171(3) 0.54112(8) -0.14886(8) 0.0315 1.0000 Uani . . . . . .
F26 F 0.15749(13) 0.6548(3) -0.2212(3) 0.0779 1.0000 Uani . . . . . .
F27 F 0.23709(10) 0.5532(4) -0.2507(2) 0.1023 1.0000 Uani . . . . . .
F28 F 0.22427(12) 0.6393(3) -0.0521(2) 0.0728 1.0000 Uani . . . . . .
F29 F 0.14394(9) 0.5331(3) -0.0435(2) 0.0559 1.0000 Uani . . . . . .
F30 F 0.15695(8) 0.4432(2) -0.2426(2) 0.0473 1.0000 Uani . . . . . .
F31 F 0.22244(10) 0.4279(3) -0.0698(3) 0.0646 1.0000 Uani . . . . . .
P32 P -0.01798(3) 0.75379(7) -0.01599(7) 0.0243 1.0000 Uani . . . . . .
F33 F -0.06002(8) 0.85365(19) -0.08584(18) 0.0417 1.0000 Uani . . . . . .
F34 F 0.00774(10) 0.8647(2) 0.07622(19) 0.0500 1.0000 Uani . . . . . .
F35 F 0.02506(8) 0.7819(2) -0.12652(19) 0.0466 1.0000 Uani . . . . . .
F36 F -0.04365(8) 0.64094(19) -0.1087(2) 0.0412 1.0000 Uani . . . . . .
F37 F -0.06161(9) 0.72344(19) 0.09332(19) 0.0441 1.0000 Uani . . . . . .
F38 F 0.02328(8) 0.6507(2) 0.0536(2) 0.0464 1.0000 Uani . . . . . .
K39 K 0.04881(2) 0.51706(6) -0.20506(6) 0.0273 1.0000 Uani . . . . . .
H42 H 0.2747 1.0219 -0.3374 0.0314 1.0000 Uiso R . . . . .
H41 H 0.2879 1.0371 -0.1835 0.0311 1.0000 Uiso R . . . . .
H52 H 0.2007 0.8944 -0.3062 0.0290 1.0000 Uiso R . . . . .
H51 H 0.2204 0.8654 -0.1582 0.0292 1.0000 Uiso R . . . . .
H73 H 0.0967 1.0323 -0.1455 0.0669 1.0000 Uiso R . . . . .
H71 H 0.1113 0.9439 -0.2668 0.0671 1.0000 Uiso R . . . . .
H72 H 0.1254 0.8979 -0.1182 0.0667 1.0000 Uiso R . . . . .
H91 H 0.1468 1.2004 -0.2449 0.0588 1.0000 Uiso R . . . . .
H92 H 0.2099 1.1884 -0.2659 0.0584 1.0000 Uiso R . . . . .
H93 H 0.1663 1.1145 -0.3596 0.0588 1.0000 Uiso R . . . . .
H83 H 0.1680 1.1357 -0.0101 0.0754 1.0000 Uiso R . . . . .
H81 H 0.2304 1.1158 -0.0393 0.0756 1.0000 Uiso R . . . . .
H82 H 0.1974 1.0029 0.0193 0.0763 1.0000 Uiso R . . . . .
H161 H 0.4337 0.7338 0.0337 0.0311 1.0000 Uiso R . . . . .
H141 H 0.4368 0.3745 0.1802 0.0385 1.0000 Uiso R . . . . .
H121 H 0.3362 0.4620 -0.1379 0.0333 1.0000 Uiso R . . . . .
H101 H 0.3558 0.6707 -0.2448 0.0331 1.0000 Uiso R . . . . .
H31 H 0.3124 0.8272 -0.3267 0.0324 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.586(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
F118 . C17 . 1.435(8) yes
F119 . C17 . 1.378(13) yes
F120 . C17 . 1.189(7) yes
C21 . F22 . 1.362(6) yes
C21 . F23 . 1.302(6) yes
C21 . F24 . 1.305(5) yes
C21 . C13 . 1.498(5) yes
C21 . F123 . 1.221(10) yes
C21 . F124 . 1.292(12) yes
C21 . F125 . 1.313(11) yes
C21 . C13 . 1.498(5) yes
S1 . C2 . 1.683(3) yes
C2 . N3 . 1.342(3) yes
C2 . N10 . 1.355(4) yes
N3 . C4 . 1.454(4) yes
N3 . H31 . 0.846 no
C4 . C5 . 1.522(4) yes
C4 . H42 . 0.967 no
C4 . H41 . 0.960 no
C5 . N6 . 1.509(3) yes
C5 . H52 . 0.962 no
C5 . H51 . 0.951 no
N6 . C7 . 1.502(4) yes
N6 . C8 . 1.490(4) yes
N6 . C9 . 1.496(4) yes
C7 . H73 . 0.963 no
C7 . H71 . 0.962 no
C7 . H72 . 0.957 no
C8 . H83 . 0.967 no
C8 . H81 . 0.961 no
C8 . H82 . 0.959 no
C9 . H91 . 0.943 no
C9 . H92 . 0.965 no
C9 . H93 . 0.961 no
N10 . C11 . 1.420(4) yes
N10 . H101 . 0.854 no
C11 . C12 . 1.381(4) yes
C11 . C16 . 1.390(4) yes
C12 . C13 . 1.393(4) yes
C12 . H121 . 0.930 no
C13 . C14 . 1.385(4) yes
C14 . C15 . 1.386(5) yes
C14 . H141 . 0.919 no
C15 . C16 . 1.383(4) yes
C15 . C17 . 1.501(4) yes
C16 . H161 . 0.928 no
C17 . F18 . 1.299(6) yes
C17 . F19 . 1.414(7) yes
C17 . F20 . 1.246(10) yes
P25 . F26 . 1.597(3) yes
P25 . F27 . 1.549(2) yes
P25 . F28 . 1.589(2) yes
P25 . F29 . 1.615(2) yes
P25 . F30 . 1.596(2) yes
P25 . F31 . 1.584(2) yes
P32 . F33 . 1.5932(19) yes
P32 . F34 . 1.5845(19) yes
P32 . F35 . 1.5920(19) yes
P32 . F36 . 1.6015(18) yes
P32 . F37 . 1.5976(19) yes
P32 . F38 . 1.603(2) 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
F22 . C21 . F23 . 105.3(4) yes
F22 . C21 . F24 . 103.1(5) yes
F23 . C21 . F24 . 109.4(5) yes
F22 . C21 . C13 . 111.2(3) yes
F23 . C21 . C13 . 113.0(4) yes
F24 . C21 . C13 . 114.1(3) yes
F123 . C21 . F124 . 105.6(10) yes
F123 . C21 . F125 . 109.7(10) yes
F124 . C21 . F125 . 102.8(10) yes
F123 . C21 . C13 . 114.8(7) yes
F124 . C21 . C13 . 113.5(7) yes
F125 . C21 . C13 . 109.8(6) yes
S1 . C2 . N3 . 121.4(2) yes
S1 . C2 . N10 . 124.5(2) yes
N3 . C2 . N10 . 114.0(2) yes
C2 . N3 . C4 . 123.3(2) yes
C2 . N3 . H31 . 117.6 no
C4 . N3 . H31 . 117.2 no
N3 . C4 . C5 . 108.3(2) yes
N3 . C4 . H42 . 109.2 no
C5 . C4 . H42 . 110.7 no
N3 . C4 . H41 . 109.3 no
C5 . C4 . H41 . 111.0 no
H42 . C4 . H41 . 108.3 no
C4 . C5 . N6 . 115.4(2) yes
C4 . C5 . H52 . 109.2 no
N6 . C5 . H52 . 106.8 no
C4 . C5 . H51 . 108.7 no
N6 . C5 . H51 . 107.5 no
H52 . C5 . H51 . 109.1 no
C5 . N6 . C7 . 107.2(2) yes
C5 . N6 . C8 . 111.0(2) yes
C7 . N6 . C8 . 108.9(3) yes
C5 . N6 . C9 . 111.8(2) yes
C7 . N6 . C9 . 108.6(3) yes
C8 . N6 . C9 . 109.2(3) yes
N6 . C7 . H73 . 109.0 no
N6 . C7 . H71 . 108.9 no
H73 . C7 . H71 . 110.1 no
N6 . C7 . H72 . 107.3 no
H73 . C7 . H72 . 110.7 no
H71 . C7 . H72 . 110.8 no
N6 . C8 . H83 . 109.3 no
N6 . C8 . H81 . 109.9 no
H83 . C8 . H81 . 109.9 no
N6 . C8 . H82 . 109.5 no
H83 . C8 . H82 . 109.9 no
H81 . C8 . H82 . 108.3 no
N6 . C9 . H91 . 109.6 no
N6 . C9 . H92 . 109.1 no
H91 . C9 . H92 . 110.7 no
N6 . C9 . H93 . 108.4 no
H91 . C9 . H93 . 108.9 no
H92 . C9 . H93 . 110.1 no
C2 . N10 . C11 . 126.0(2) yes
C2 . N10 . H101 . 115.6 no
C11 . N10 . H101 . 115.8 no
N10 . C11 . C12 . 118.2(2) yes
N10 . C11 . C16 . 121.3(3) yes
C12 . C11 . C16 . 120.4(3) yes
C11 . C12 . C13 . 119.6(3) yes
C11 . C12 . H121 . 120.6 no
C13 . C12 . H121 . 119.7 no
C21 . C13 . C12 . 119.7(3) yes
C21 . C13 . C14 . 119.6(3) yes
C12 . C13 . C14 . 120.7(3) yes
C13 . C14 . C15 . 118.8(3) yes
C13 . C14 . H141 . 120.2 no
C15 . C14 . H141 . 121.0 no
C14 . C15 . C16 . 121.4(3) yes
C14 . C15 . C17 . 118.3(3) yes
C16 . C15 . C17 . 120.3(3) yes
C11 . C16 . C15 . 119.2(3) yes
C11 . C16 . H161 . 120.3 no
C15 . C16 . H161 . 120.5 no
C15 . C17 . F118 . 108.9(3) yes
C15 . C17 . F119 . 111.3(7) yes
F118 . C17 . F119 . 97.2(7) yes
C15 . C17 . F120 . 118.4(4) yes
F118 . C17 . F120 . 107.6(6) yes
F119 . C17 . F120 . 111.2(8) yes
C15 . C17 . F18 . 113.6(3) yes
C15 . C17 . F19 . 108.8(3) yes
F18 . C17 . F19 . 101.0(5) yes
C15 . C17 . F20 . 114.3(6) yes
F18 . C17 . F20 . 113.4(6) yes
F19 . C17 . F20 . 104.4(6) yes
F26 . P25 . F27 . 90.9(2) yes
F26 . P25 . F28 . 91.73(15) yes
F27 . P25 . F28 . 89.81(16) yes
F26 . P25 . F29 . 87.48(15) yes
F27 . P25 . F29 . 178.2(2) yes
F28 . P25 . F29 . 89.43(14) yes
F26 . P25 . F30 . 87.71(13) yes
F27 . P25 . F30 . 92.39(14) yes
F28 . P25 . F30 . 177.74(14) yes
F29 . P25 . F30 . 88.36(12) yes
F26 . P25 . F31 . 176.02(16) yes
F27 . P25 . F31 . 93.05(18) yes
F28 . P25 . F31 . 88.19(15) yes
F29 . P25 . F31 . 88.54(14) yes
F30 . P25 . F31 . 92.22(14) yes
F33 . P32 . F34 . 90.22(12) yes
F33 . P32 . F35 . 90.49(11) yes
F34 . P32 . F35 . 90.85(12) yes
F33 . P32 . F36 . 90.22(11) yes
F34 . P32 . F36 . 179.56(12) yes
F35 . P32 . F36 . 89.13(11) yes
F33 . P32 . F37 . 89.56(11) yes
F34 . P32 . F37 . 90.19(12) yes
F35 . P32 . F37 . 178.96(12) yes
F36 . P32 . F37 . 89.82(11) yes
F33 . P32 . F38 . 178.67(12) yes
F34 . P32 . F38 . 90.94(12) yes
F35 . P32 . F38 . 90.14(12) yes
F36 . P32 . F38 . 88.62(11) yes
F37 . P32 . F38 . 89.78(11) yes


_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_I_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1585754'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   8.64540(10)
_cell_length_b                   9.46300(10)
_cell_length_c                   20.0392(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.7530(9)
_cell_angle_gamma                90
_cell_volume                     1628.06(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
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
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'
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'


_cell_formula_units_Z            2

# Given Formula = C34 H40 N4 O8 S1 
# Dc =      1.36 Fooo =    704.00 Mu =     13.73 M =    664.78
# Found Formula = C34 H42 N4 O8 S1 
# Dc =      1.36 FOOO =    708.00 Mu =     13.73 M =    666.80

_chemical_formula_sum            'C34 H42 N4 O8 S'
_chemical_formula_moiety         '2(C17 H19 N2 O), O4 S, 2(H2 O)'
_chemical_compound_source        ?
_chemical_formula_weight         666.80


_cell_measurement_reflns_used    19459
_cell_measurement_theta_min      5
_cell_measurement_theta_max      79
_cell_measurement_temperature    160

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.025
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_max          0.079

_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    1.373

# Sheldrick geometric approximatio 0.93 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.81
_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     1.54184
_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      160
_diffrn_reflns_number            34569
_reflns_number_total             6613
_diffrn_reflns_av_R_equivalents  0.035
# Number of reflections without Friedels Law is 6613 
# Number of reflections with Friedels Law is 3530 
# Theoretical number of reflections is about 3330 


_diffrn_reflns_theta_min         4.444
_diffrn_reflns_theta_max         74.500
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        74.500
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   2.31
_oxford_diffrn_Wilson_scale      0.44

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

_refine_diff_density_min         -0.39
_refine_diff_density_max         0.80


# 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         6613
_refine_ls_number_restraints     5
_refine_ls_number_parameters     425
_oxford_refine_ls_R_factor_ref   0.0441
_refine_ls_wR_factor_ref         0.1063
_refine_ls_goodness_of_fit_ref   0.9540
_refine_ls_shift/su_max          0.0004127
_refine_ls_shift/su_mean         0.0000257


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6613
_refine_ls_R_factor_all          0.0441
_refine_ls_wR_factor_all         0.1063

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6209
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_gt          0.1038

_refine_ls_abs_structure_Flack   0.114(15)
_refine_ls_abs_structure_details 'Flack (1983), 3083 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) + ( 0.06P)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
N1 N 0.3773(2) 0.9999(2) 0.41828(11) 0.0335 1.0000 Uani . . . . . .
C2 C 0.3669(3) 1.0104(3) 0.34308(13) 0.0340 1.0000 Uani . . . . . .
C3 C 0.2156(3) 1.0786(3) 0.31424(12) 0.0297 1.0000 Uani . . . . . .
C4 C 0.0748(3) 0.9873(2) 0.31475(11) 0.0260 1.0000 Uani . . . . . .
C5 C -0.0138(3) 0.9634(3) 0.36617(12) 0.0310 1.0000 Uani D . . . . .
N6 N -0.1268(2) 0.8658(2) 0.34739(10) 0.0307 1.0000 Uani . . . . . .
C7 C -0.1154(3) 0.8249(2) 0.28237(11) 0.0254 1.0000 Uani . . . . . .
C8 C 0.0096(2) 0.8994(2) 0.26002(11) 0.0236 1.0000 Uani . . . . . .
C9 C -0.2040(3) 0.7286(3) 0.24064(12) 0.0289 1.0000 Uani . . . . . .
C10 C -0.1677(3) 0.7130(2) 0.17608(12) 0.0284 1.0000 Uani . . . . . .
C11 C -0.0469(2) 0.7908(2) 0.15207(11) 0.0238 1.0000 Uani . . . . . .
C12 C 0.0438(2) 0.8831(2) 0.19341(11) 0.0224 1.0000 Uani . . . . . .
O13 O -0.02904(19) 0.76648(17) 0.08558(8) 0.0296 1.0000 Uani . . . . . .
C14 C 0.0754(3) 0.8592(2) 0.05561(11) 0.0262 1.0000 Uani . . . . . .
C15 C 0.0755(2) 0.8173(2) -0.01655(11) 0.0247 1.0000 Uani . . . . . .
C16 C -0.0079(3) 0.8936(3) -0.06775(12) 0.0322 1.0000 Uani . . . . . .
C17 C -0.0068(3) 0.8550(3) -0.13469(13) 0.0374 1.0000 Uani . . . . . .
C18 C 0.0757(3) 0.7374(3) -0.15049(13) 0.0342 1.0000 Uani . . . . . .
C19 C 0.1618(3) 0.6610(3) -0.09974(13) 0.0331 1.0000 Uani . . . . . .
C20 C 0.1629(3) 0.7014(2) -0.03354(12) 0.0285 1.0000 Uani . . . . . .
N21 N 0.8608(2) 0.4405(2) 0.39090(10) 0.0299 1.0000 Uani . . . . . .
C22 C 0.8651(3) 0.3567(3) 0.32791(12) 0.0306 1.0000 Uani . . . . . .
C23 C 0.7253(2) 0.2564(2) 0.31775(11) 0.0267 1.0000 Uani . . . . . .
C24 C 0.5753(2) 0.3378(2) 0.31411(10) 0.0224 1.0000 Uani . . . . . .
C25 C 0.4877(3) 0.3630(2) 0.36566(11) 0.0263 1.0000 Uani D . . . . .
N26 N 0.3687(2) 0.4544(2) 0.34472(9) 0.0261 1.0000 Uani D . . . . .
C27 C 0.3793(2) 0.4926(2) 0.27895(11) 0.0229 1.0000 Uani . . . . . .
C28 C 0.5066(2) 0.4191(2) 0.25775(10) 0.0206 1.0000 Uani . . . . . .
C29 C 0.2897(3) 0.5846(2) 0.23665(12) 0.0277 1.0000 Uani . . . . . .
C30 C 0.3268(3) 0.5994(2) 0.17190(12) 0.0274 1.0000 Uani . . . . . .
C31 C 0.4510(2) 0.5229(2) 0.14907(11) 0.0233 1.0000 Uani . . . . . .
C32 C 0.5425(2) 0.4338(2) 0.19116(10) 0.0210 1.0000 Uani . . . . . .
O33 O 0.46865(19) 0.54587(17) 0.08260(8) 0.0288 1.0000 Uani . . . . . .
C34 C 0.5775(3) 0.4555(2) 0.05394(11) 0.0246 1.0000 Uani . . . . . .
C35 C 0.5762(2) 0.4949(2) -0.01860(11) 0.0239 1.0000 Uani . . . . . .
C36 C 0.4942(3) 0.4154(3) -0.06877(12) 0.0312 1.0000 Uani . . . . . .
C37 C 0.4929(3) 0.4535(3) -0.13586(13) 0.0370 1.0000 Uani . . . . . .
C38 C 0.5708(3) 0.5724(3) -0.15280(12) 0.0356 1.0000 Uani . . . . . .
C39 C 0.6555(3) 0.6506(3) -0.10345(12) 0.0335 1.0000 Uani . . . . . .
C40 C 0.6602(2) 0.6126(2) -0.03627(11) 0.0277 1.0000 Uani . . . . . .
S41 S 0.23514(5) 0.63341(7) 0.48521(3) 0.0247 1.0000 Uani . . . . . .
O42 O 0.1533(2) 0.5473(3) 0.43157(12) 0.0601 1.0000 Uani . . . . . .
O43 O 0.12206(19) 0.7231(2) 0.51437(9) 0.0375 1.0000 Uani D . . . . .
O44 O 0.3109(2) 0.5395(3) 0.53619(12) 0.0600 1.0000 Uani . . . . . .
O45 O 0.3532(2) 0.7200(2) 0.45852(11) 0.0452 1.0000 Uani . . . . . .
O46 O 0.6456(2) 0.6712(2) 0.40548(10) 0.0441 1.0000 Uani D . . . . .
O47 O 0.1894(2) 1.2394(2) 0.47226(10) 0.0379 1.0000 Uani D . . . . .
H121 H 0.1254 0.9354 0.1772 0.0268 1.0000 Uiso R . . . . .
H51 H -0.0020 1.0063 0.4089 0.0376 1.0000 Uiso R . . . . .
H31 H 0.2030 1.1646 0.3389 0.0355 1.0000 Uiso R . . . . .
H32 H 0.2251 1.1040 0.2680 0.0368 1.0000 Uiso R . . . . .
H22 H 0.4565 1.0663 0.3336 0.0403 1.0000 Uiso R . . . . .
H21 H 0.3769 0.9183 0.3252 0.0398 1.0000 Uiso R . . . . .
H91 H -0.2862 0.6784 0.2552 0.0350 1.0000 Uiso R . . . . .
H101 H -0.2243 0.6479 0.1473 0.0346 1.0000 Uiso R . . . . .
H141 H 0.1799 0.8505 0.0794 0.0306 1.0000 Uiso R . . . . .
H142 H 0.0425 0.9554 0.0595 0.0311 1.0000 Uiso R . . . . .
H201 H 0.2240 0.6507 0.0005 0.0345 1.0000 Uiso R . . . . .
H191 H 0.2194 0.5815 -0.1114 0.0396 1.0000 Uiso R . . . . .
H181 H 0.0717 0.7099 -0.1957 0.0417 1.0000 Uiso R . . . . .
H171 H -0.0650 0.9031 -0.1692 0.0449 1.0000 Uiso R . . . . .
H161 H -0.0629 0.9741 -0.0570 0.0396 1.0000 Uiso R . . . . .
H321 H 0.6259 0.3837 0.1775 0.0248 1.0000 Uiso R . . . . .
H251 H 0.5015 0.3280 0.4109 0.0320 1.0000 Uiso R . . . . .
H232 H 0.7356 0.1911 0.3549 0.0328 1.0000 Uiso R . . . . .
H231 H 0.7313 0.2067 0.2750 0.0321 1.0000 Uiso R . . . . .
H222 H 0.9620 0.3021 0.3319 0.0372 1.0000 Uiso R . . . . .
H221 H 0.8688 0.4227 0.2894 0.0368 1.0000 Uiso R . . . . .
H291 H 0.2036 0.6341 0.2507 0.0340 1.0000 Uiso R . . . . .
H301 H 0.2701 0.6619 0.1414 0.0324 1.0000 Uiso R . . . . .
H342 H 0.6794 0.4730 0.0771 0.0289 1.0000 Uiso R . . . . .
H341 H 0.5437 0.3575 0.0590 0.0295 1.0000 Uiso R . . . . .
H401 H 0.7210 0.6610 -0.0036 0.0337 1.0000 Uiso R . . . . .
H391 H 0.7087 0.7299 -0.1147 0.0409 1.0000 Uiso R . . . . .
H381 H 0.5644 0.6004 -0.1984 0.0427 1.0000 Uiso R . . . . .
H371 H 0.4378 0.3978 -0.1697 0.0443 1.0000 Uiso R . . . . .
H361 H 0.4390 0.3355 -0.0577 0.0360 1.0000 Uiso R . . . . .
H12 H 0.3198 1.0695 0.4349 0.0500 1.0000 Uiso R . . . . .
H61 H -0.1966 0.8362 0.3718 0.0371 1.0000 Uiso R . . . . .
H261 H 0.3019 0.4874 0.3701 0.0315 1.0000 Uiso R . . . . .
H213 H 0.8540 0.3788 0.4254 0.0452 1.0000 Uiso R . . . . .
H13 H 0.3416 0.9125 0.4293 0.0497 1.0000 Uiso R . . . . .
H462 H 0.6866 0.6990 0.4454 0.0678 1.0000 Uiso DR . . . . .
H471 H 0.1781 1.3227 0.4640 0.0575 1.0000 Uiso DR . . . . .
H211 H 0.9478 0.4880 0.4001 0.0453 1.0000 Uiso R . . . . .
H212 H 0.7797 0.5016 0.3887 0.0450 1.0000 Uiso R . . . . .
H11 H 0.4785 1.0100 0.4361 0.0496 1.0000 Uiso R . . . . .
H461 H 0.5497 0.6689 0.4073 0.0660 1.0000 Uiso R . . . . .
H472 H 0.0960 1.2284 0.4792 0.0576 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.476(7)
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 . 1.502(3) yes
N1 . H12 . 0.911 no
N1 . H13 . 0.919 no
N1 . H11 . 0.910 no
C2 . C3 . 1.512(3) yes
C2 . H22 . 0.975 no
C2 . H21 . 0.950 no
C3 . C4 . 1.494(3) yes
C3 . H31 . 0.965 no
C3 . H32 . 0.971 no
C4 . C5 . 1.373(3) yes
C4 . C8 . 1.438(3) yes
C5 . N6 . 1.365(3) yes
C5 . H51 . 0.942 no
N6 . C7 . 1.374(3) yes
N6 . H61 . 0.867 no
C7 . C8 . 1.407(3) yes
C7 . C9 . 1.402(3) yes
C8 . C12 . 1.409(3) yes
C9 . C10 . 1.374(3) yes
C9 . H91 . 0.930 no
C10 . C11 . 1.408(3) yes
C10 . H101 . 0.941 no
C11 . C12 . 1.383(3) yes
C11 . O13 . 1.379(3) yes
C12 . H121 . 0.950 no
O13 . C14 . 1.440(3) yes
C14 . C15 . 1.499(3) yes
C14 . H141 . 0.974 no
C14 . H142 . 0.960 no
C15 . C16 . 1.385(3) yes
C15 . C20 . 1.396(3) yes
C16 . C17 . 1.391(3) yes
C16 . H161 . 0.937 no
C17 . C18 . 1.379(4) yes
C17 . H171 . 0.926 no
C18 . C19 . 1.390(4) yes
C18 . H181 . 0.940 no
C19 . C20 . 1.380(3) yes
C19 . H191 . 0.945 no
C20 . H201 . 0.943 no
N21 . C22 . 1.495(3) yes
N21 . H213 . 0.912 no
N21 . H211 . 0.877 no
N21 . H212 . 0.906 no
C22 . C23 . 1.531(3) yes
C22 . H222 . 0.979 no
C22 . H221 . 0.996 no
C23 . C24 . 1.503(3) yes
C23 . H232 . 0.963 no
C23 . H231 . 0.983 no
C24 . C25 . 1.371(3) yes
C24 . C28 . 1.436(3) yes
C25 . N26 . 1.371(3) yes
C25 . H251 . 0.960 no
N26 . C27 . 1.380(3) yes
N26 . H261 . 0.871 no
C27 . C28 . 1.409(3) yes
C27 . C29 . 1.386(3) yes
C28 . C32 . 1.412(3) yes
C29 . C30 . 1.380(3) yes
C29 . H291 . 0.950 no
C30 . C31 . 1.415(3) yes
C30 . H301 . 0.946 no
C31 . C32 . 1.375(3) yes
C31 . O33 . 1.376(3) yes
C32 . H321 . 0.930 no
O33 . C34 . 1.440(2) yes
C34 . C35 . 1.500(3) yes
C34 . H342 . 0.961 no
C34 . H341 . 0.980 no
C35 . C36 . 1.383(3) yes
C35 . C40 . 1.398(3) yes
C36 . C37 . 1.391(3) yes
C36 . H361 . 0.935 no
C37 . C38 . 1.375(4) yes
C37 . H371 . 0.943 no
C38 . C39 . 1.375(4) yes
C38 . H381 . 0.946 no
C39 . C40 . 1.389(3) yes
C39 . H391 . 0.922 no
C40 . H401 . 0.912 no
S41 . O42 . 1.4633(18) yes
S41 . O43 . 1.4667(17) yes
S41 . O44 . 1.451(2) yes
S41 . O45 . 1.4582(18) yes
O46 . H462 . 0.877 no
O46 . H461 . 0.835 no
O47 . H471 . 0.809 no
O47 . H472 . 0.841 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 . H12 . 110.3 no
C2 . N1 . H13 . 108.6 no
H12 . N1 . H13 . 110.5 no
C2 . N1 . H11 . 109.1 no
H12 . N1 . H11 . 108.8 no
H13 . N1 . H11 . 109.5 no
N1 . C2 . C3 . 111.01(19) yes
N1 . C2 . H22 . 106.0 no
C3 . C2 . H22 . 111.4 no
N1 . C2 . H21 . 108.7 no
C3 . C2 . H21 . 111.1 no
H22 . C2 . H21 . 108.4 no
C2 . C3 . C4 . 114.8(2) yes
C2 . C3 . H31 . 108.0 no
C4 . C3 . H31 . 110.0 no
C2 . C3 . H32 . 107.7 no
C4 . C3 . H32 . 108.1 no
H31 . C3 . H32 . 108.0 no
C3 . C4 . C5 . 128.8(2) yes
C3 . C4 . C8 . 125.2(2) yes
C5 . C4 . C8 . 105.92(19) yes
C4 . C5 . N6 . 110.4(2) yes
C4 . C5 . H51 . 127.0 no
N6 . C5 . H51 . 122.6 no
C5 . N6 . C7 . 108.86(19) yes
C5 . N6 . H61 . 126.0 no
C7 . N6 . H61 . 125.2 no
N6 . C7 . C8 . 107.7(2) yes
N6 . C7 . C9 . 130.8(2) yes
C8 . C7 . C9 . 121.5(2) yes
C4 . C8 . C7 . 107.08(19) yes
C4 . C8 . C12 . 132.7(2) yes
C7 . C8 . C12 . 120.10(19) yes
C7 . C9 . C10 . 117.5(2) yes
C7 . C9 . H91 . 122.0 no
C10 . C9 . H91 . 120.5 no
C9 . C10 . C11 . 121.7(2) yes
C9 . C10 . H101 . 119.2 no
C11 . C10 . H101 . 119.1 no
C10 . C11 . C12 . 121.1(2) yes
C10 . C11 . O13 . 114.50(19) yes
C12 . C11 . O13 . 124.38(19) yes
C8 . C12 . C11 . 117.99(19) yes
C8 . C12 . H121 . 121.0 no
C11 . C12 . H121 . 121.0 no
C11 . O13 . C14 . 116.64(17) yes
O13 . C14 . C15 . 108.21(18) yes
O13 . C14 . H141 . 109.6 no
C15 . C14 . H141 . 110.2 no
O13 . C14 . H142 . 109.7 no
C15 . C14 . H142 . 111.3 no
H141 . C14 . H142 . 107.9 no
C14 . C15 . C16 . 121.2(2) yes
C14 . C15 . C20 . 120.3(2) yes
C16 . C15 . C20 . 118.6(2) yes
C15 . C16 . C17 . 121.0(2) yes
C15 . C16 . H161 . 119.2 no
C17 . C16 . H161 . 119.8 no
C16 . C17 . C18 . 119.7(2) yes
C16 . C17 . H171 . 121.8 no
C18 . C17 . H171 . 118.4 no
C17 . C18 . C19 . 119.9(2) yes
C17 . C18 . H181 . 118.9 no
C19 . C18 . H181 . 121.1 no
C18 . C19 . C20 . 120.1(2) yes
C18 . C19 . H191 . 119.0 no
C20 . C19 . H191 . 120.9 no
C15 . C20 . C19 . 120.7(2) yes
C15 . C20 . H201 . 119.8 no
C19 . C20 . H201 . 119.5 no
C22 . N21 . H213 . 108.2 no
C22 . N21 . H211 . 110.1 no
H213 . N21 . H211 . 107.4 no
C22 . N21 . H212 . 113.2 no
H213 . N21 . H212 . 109.0 no
H211 . N21 . H212 . 108.8 no
N21 . C22 . C23 . 110.09(19) yes
N21 . C22 . H222 . 108.5 no
C23 . C22 . H222 . 109.8 no
N21 . C22 . H221 . 109.1 no
C23 . C22 . H221 . 112.5 no
H222 . C22 . H221 . 106.8 no
C22 . C23 . C24 . 110.58(19) yes
C22 . C23 . H232 . 107.2 no
C24 . C23 . H232 . 111.5 no
C22 . C23 . H231 . 106.9 no
C24 . C23 . H231 . 109.6 no
H232 . C23 . H231 . 110.9 no
C23 . C24 . C25 . 127.0(2) yes
C23 . C24 . C28 . 125.96(18) yes
C25 . C24 . C28 . 106.61(18) yes
C24 . C25 . N26 . 109.8(2) yes
C24 . C25 . H251 . 129.3 no
N26 . C25 . H251 . 120.8 no
C25 . N26 . C27 . 109.03(18) yes
C25 . N26 . H261 . 124.9 no
C27 . N26 . H261 . 125.9 no
N26 . C27 . C28 . 107.48(19) yes
N26 . C27 . C29 . 130.8(2) yes
C28 . C27 . C29 . 121.69(19) yes
C24 . C28 . C27 . 107.00(18) yes
C24 . C28 . C32 . 132.81(19) yes
C27 . C28 . C32 . 120.18(19) yes
C27 . C29 . C30 . 117.6(2) yes
C27 . C29 . H291 . 121.9 no
C30 . C29 . H291 . 120.4 no
C29 . C30 . C31 . 121.4(2) yes
C29 . C30 . H301 . 120.8 no
C31 . C30 . H301 . 117.8 no
C30 . C31 . C32 . 121.3(2) yes
C30 . C31 . O33 . 114.03(19) yes
C32 . C31 . O33 . 124.70(19) yes
C28 . C32 . C31 . 117.72(19) yes
C28 . C32 . H321 . 119.5 no
C31 . C32 . H321 . 122.7 no
C31 . O33 . C34 . 116.38(16) yes
O33 . C34 . C35 . 107.94(17) yes
O33 . C34 . H342 . 108.1 no
C35 . C34 . H342 . 109.1 no
O33 . C34 . H341 . 107.7 no
C35 . C34 . H341 . 111.5 no
H342 . C34 . H341 . 112.4 no
C34 . C35 . C36 . 120.9(2) yes
C34 . C35 . C40 . 119.9(2) yes
C36 . C35 . C40 . 119.1(2) yes
C35 . C36 . C37 . 120.5(2) yes
C35 . C36 . H361 . 120.0 no
C37 . C36 . H361 . 119.5 no
C36 . C37 . C38 . 120.2(2) yes
C36 . C37 . H371 . 119.8 no
C38 . C37 . H371 . 120.1 no
C37 . C38 . C39 . 119.9(2) yes
C37 . C38 . H381 . 119.5 no
C39 . C38 . H381 . 120.6 no
C38 . C39 . C40 . 120.7(2) yes
C38 . C39 . H391 . 120.0 no
C40 . C39 . H391 . 119.3 no
C35 . C40 . C39 . 119.7(2) yes
C35 . C40 . H401 . 119.4 no
C39 . C40 . H401 . 120.9 no
O42 . S41 . O43 . 109.11(10) yes
O42 . S41 . O44 . 108.39(16) yes
O43 . S41 . O44 . 109.92(12) yes
O42 . S41 . O45 . 110.01(13) yes
O43 . S41 . O45 . 110.44(12) yes
O44 . S41 . O45 . 108.94(12) yes
H462 . O46 . H461 . 105.4 no
H471 . O47 . H472 . 93.4 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
N1 . H12 . O47 . 178 0.91 2.15 3.059(3) yes
N6 . H61 . O46 1_455 153 0.87 2.23 3.026(3) yes
N26 . H261 . O42 . 175 0.87 1.96 2.834(3) yes
N21 . H213 . O43 2_646 165 0.91 1.90 2.791(3) yes
N1 . H13 . O45 . 158 0.92 1.91 2.784(3) yes
O46 . H462 . O47 2_646 169 0.88 1.90 2.763(3) yes
O47 . H471 . O42 1_565 174 0.81 2.23 3.032(3) yes
N21 . H211 . O42 1_655 165 0.88 1.90 2.756(3) yes
N21 . H212 . O46 . 162 0.91 2.03 2.905(3) yes
N1 . H11 . O44 2_656 174 0.91 1.86 2.768(3) yes
O46 . H461 . O45 . 150 0.83 2.14 2.893(3) yes
O47 . H472 . O43 2_556 172 0.84 1.91 2.741(3) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_I_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1585749'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   20.7561(2)
_cell_length_b                   9.51340(10)
_cell_length_c                   8.53520(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.5078(9)
_cell_angle_gamma                90
_cell_volume                     1674.51(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-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'
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'
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'
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            4

# Given Formula = C17 H21 N2 O5 P1 
# Dc =      1.45 Fooo =    768.00 Mu =     17.41 M =    364.34
# Found Formula = C17 H21 N2 O5 P1 
# Dc =      1.45 FOOO =    768.00 Mu =     17.41 M =    364.34

_chemical_formula_sum            'C17 H21 N2 O5 P'
_chemical_formula_moiety         'C17 H19 N2 O, H2 O4 P'
_chemical_compound_source        ?
_chemical_formula_weight         364.34


_cell_measurement_reflns_used    20115
_cell_measurement_theta_min      4
_cell_measurement_theta_max      79
_cell_measurement_temperature    160

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.012
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_max          0.233

_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    1.741

# Sheldrick geometric approximatio 0.77 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.98
_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      160
_diffrn_reflns_number            34497
_reflns_number_total             3487
_diffrn_reflns_av_R_equivalents  0.030
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3487 
# Theoretical number of reflections is about 6980 


_diffrn_reflns_theta_min         4.288
_diffrn_reflns_theta_max         75.865
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        75.865
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              -26
_reflns_limit_h_max              25
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   1.77
_oxford_diffrn_Wilson_scale      0.07

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

_refine_diff_density_min         -0.38
_refine_diff_density_max         0.25


# 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         3487
_refine_ls_number_restraints     0
_refine_ls_number_parameters     226
_oxford_refine_ls_R_factor_ref   0.0312
_refine_ls_wR_factor_ref         0.0761
_refine_ls_goodness_of_fit_ref   0.9648
_refine_ls_shift/su_max          0.0030691
_refine_ls_shift/su_mean         0.0001178


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3487
_refine_ls_R_factor_all          0.0312
_refine_ls_wR_factor_all         0.0761

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3276
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_gt          0.0750

# 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 .


_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 + 1.09P] 
 ,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 0.87287(5) 0.55192(12) 0.07757(13) 0.0247 1.0000 Uani . . . . . .
C2 C 0.81491(6) 0.45898(15) 0.04629(16) 0.0259 1.0000 Uani . . . . . .
C3 C 0.81101(6) 0.35823(14) 0.18470(16) 0.0250 1.0000 Uani . . . . . .
C4 C 0.80654(6) 0.43599(14) 0.33574(15) 0.0222 1.0000 Uani . . . . . .
C5 C 0.85641(6) 0.46226(15) 0.45182(16) 0.0257 1.0000 Uani . . . . . .
N6 N 0.83600(5) 0.54900(13) 0.56404(13) 0.0260 1.0000 Uani . . . . . .
C7 C 0.77203(6) 0.58411(14) 0.52050(15) 0.0223 1.0000 Uani . . . . . .
C8 C 0.75143(6) 0.51267(13) 0.37851(14) 0.0206 1.0000 Uani . . . . . .
C9 C 0.73086(7) 0.67340(15) 0.59171(16) 0.0258 1.0000 Uani . . . . . .
C10 C 0.66810(7) 0.68767(15) 0.52082(16) 0.0265 1.0000 Uani . . . . . .
C11 C 0.64585(6) 0.61293(14) 0.38239(15) 0.0229 1.0000 Uani . . . . . .
C12 C 0.68663(6) 0.52616(13) 0.30963(15) 0.0216 1.0000 Uani . . . . . .
O13 O 0.58133(4) 0.63559(11) 0.32981(12) 0.0293 1.0000 Uani . . . . . .
C14 C 0.55347(6) 0.54733(15) 0.20256(16) 0.0256 1.0000 Uani . . . . . .
C15 C 0.48373(6) 0.58982(14) 0.16337(15) 0.0243 1.0000 Uani . . . . . .
C16 C 0.43416(7) 0.51128(17) 0.21618(17) 0.0314 1.0000 Uani . . . . . .
C17 C 0.36977(7) 0.55160(18) 0.17959(18) 0.0354 1.0000 Uani . . . . . .
C18 C 0.35478(7) 0.67164(17) 0.09232(18) 0.0332 1.0000 Uani . . . . . .
C19 C 0.40375(7) 0.74891(16) 0.03626(17) 0.0324 1.0000 Uani . . . . . .
C20 C 0.46793(7) 0.70757(15) 0.07031(17) 0.0280 1.0000 Uani . . . . . .
P21 P 0.979394(14) 0.69786(3) 0.78570(3) 0.0162 1.0000 Uani . . . . . .
O22 O 0.91040(4) 0.69810(10) 0.82255(10) 0.0240 1.0000 Uani . . . . . .
O23 O 1.00063(5) 0.83403(9) 0.71518(10) 0.0231 1.0000 Uani . . . . . .
O24 O 1.02778(4) 0.65647(10) 0.93328(10) 0.0219 1.0000 Uani . . . . . .
O25 O 0.99123(4) 0.58288(9) 0.66018(10) 0.0224 1.0000 Uani . . . . . .
H121 H 0.6719 0.4771 0.2166 0.0258 1.0000 Uiso R . . . . .
H51 H 0.8994 0.4292 0.4579 0.0309 1.0000 Uiso R . . . . .
H32 H 0.8490 0.2991 0.1945 0.0280 1.0000 Uiso R . . . . .
H31 H 0.7729 0.2978 0.1585 0.0302 1.0000 Uiso R . . . . .
H21 H 0.8205 0.4069 -0.0497 0.0312 1.0000 Uiso R . . . . .
H22 H 0.7756 0.5191 0.0292 0.0314 1.0000 Uiso R . . . . .
H91 H 0.7456 0.7211 0.6868 0.0318 1.0000 Uiso R . . . . .
H101 H 0.6394 0.7474 0.5643 0.0313 1.0000 Uiso R . . . . .
H142 H 0.5771 0.5617 0.1123 0.0306 1.0000 Uiso R . . . . .
H141 H 0.5567 0.4485 0.2359 0.0309 1.0000 Uiso R . . . . .
H201 H 0.5009 0.7597 0.0284 0.0341 1.0000 Uiso R . . . . .
H191 H 0.3936 0.8306 -0.0247 0.0392 1.0000 Uiso R . . . . .
H181 H 0.3104 0.7029 0.0711 0.0396 1.0000 Uiso R . . . . .
H171 H 0.3363 0.4999 0.2161 0.0423 1.0000 Uiso R . . . . .
H161 H 0.4450 0.4285 0.2765 0.0381 1.0000 Uiso R . . . . .
H61 H 0.8601 0.5848 0.6427 0.0321 1.0000 Uiso R . . . . .
H13 H 0.8771 0.6095 -0.0077 0.0379 1.0000 Uiso R . . . . .
H12 H 0.9087 0.4973 0.0912 0.0377 1.0000 Uiso R . . . . .
H11 H 0.8707 0.6045 0.1674 0.0383 1.0000 Uiso R . . . . .
H241 H 1.0153 0.6669 1.0202 0.0367 1.0000 Uiso R . . . . .
H251 H 0.9920 0.5015 0.6977 0.0374 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.66(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 . 1.4924(17) yes
N1 . H13 . 0.923 no
N1 . H12 . 0.903 no
N1 . H11 . 0.921 no
C2 . C3 . 1.5305(19) yes
C2 . H21 . 0.976 no
C2 . H22 . 0.993 no
C3 . C4 . 1.4984(18) yes
C3 . H32 . 0.964 no
C3 . H31 . 0.983 no
C4 . C5 . 1.3723(18) yes
C4 . C8 . 1.4382(18) yes
C5 . N6 . 1.3675(18) yes
C5 . H51 . 0.943 no
N6 . C7 . 1.3786(17) yes
N6 . H61 . 0.861 no
C7 . C8 . 1.4128(17) yes
C7 . C9 . 1.3924(19) yes
C8 . C12 . 1.4113(17) yes
C9 . C10 . 1.3795(19) yes
C9 . H91 . 0.949 no
C10 . C11 . 1.4111(18) yes
C10 . H101 . 0.931 no
C11 . C12 . 1.3793(18) yes
C11 . O13 . 1.3803(15) yes
C12 . H121 . 0.942 no
O13 . C14 . 1.4411(15) yes
C14 . C15 . 1.5036(18) yes
C14 . H142 . 0.968 no
C14 . H141 . 0.982 no
C15 . C16 . 1.387(2) yes
C15 . C20 . 1.3907(19) yes
C16 . C17 . 1.391(2) yes
C16 . H161 . 0.953 no
C17 . C18 . 1.380(2) yes
C17 . H171 . 0.933 no
C18 . C19 . 1.383(2) yes
C18 . H181 . 0.965 no
C19 . C20 . 1.388(2) yes
C19 . H191 . 0.946 no
C20 . H201 . 0.947 no
P21 . O22 . 1.5005(9) yes
P21 . O23 . 1.5150(9) yes
P21 . O24 . 1.5695(9) yes
P21 . O25 . 1.5697(9) yes
O24 . H241 . 0.820 no
O25 . H251 . 0.837 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 . H13 . 110.9 no
C2 . N1 . H12 . 108.5 no
H13 . N1 . H12 . 107.1 no
C2 . N1 . H11 . 110.8 no
H13 . N1 . H11 . 110.6 no
H12 . N1 . H11 . 108.9 no
N1 . C2 . C3 . 110.18(10) yes
N1 . C2 . H21 . 106.3 no
C3 . C2 . H21 . 110.6 no
N1 . C2 . H22 . 108.5 no
C3 . C2 . H22 . 111.1 no
H21 . C2 . H22 . 110.0 no
C2 . C3 . C4 . 111.64(11) yes
C2 . C3 . H32 . 108.5 no
C4 . C3 . H32 . 110.1 no
C2 . C3 . H31 . 107.6 no
C4 . C3 . H31 . 110.9 no
H32 . C3 . H31 . 107.9 no
C3 . C4 . C5 . 126.57(12) yes
C3 . C4 . C8 . 126.69(11) yes
C5 . C4 . C8 . 106.32(11) yes
C4 . C5 . N6 . 110.32(12) yes
C4 . C5 . H51 . 127.7 no
N6 . C5 . H51 . 122.0 no
C5 . N6 . C7 . 108.83(11) yes
C5 . N6 . H61 . 125.9 no
C7 . N6 . H61 . 124.9 no
N6 . C7 . C8 . 107.66(11) yes
N6 . C7 . C9 . 130.54(12) yes
C8 . C7 . C9 . 121.79(12) yes
C4 . C8 . C7 . 106.83(11) yes
C4 . C8 . C12 . 133.49(12) yes
C7 . C8 . C12 . 119.68(12) yes
C7 . C9 . C10 . 117.67(12) yes
C7 . C9 . H91 . 120.7 no
C10 . C9 . H91 . 121.6 no
C9 . C10 . C11 . 121.38(12) yes
C9 . C10 . H101 . 120.1 no
C11 . C10 . H101 . 118.5 no
C10 . C11 . C12 . 121.29(12) yes
C10 . C11 . O13 . 114.01(11) yes
C12 . C11 . O13 . 124.70(12) yes
C8 . C12 . C11 . 118.12(12) yes
C8 . C12 . H121 . 120.6 no
C11 . C12 . H121 . 121.2 no
C11 . O13 . C14 . 116.47(10) yes
O13 . C14 . C15 . 107.76(10) yes
O13 . C14 . H142 . 108.8 no
C15 . C14 . H142 . 110.2 no
O13 . C14 . H141 . 109.3 no
C15 . C14 . H141 . 110.8 no
H142 . C14 . H141 . 109.9 no
C14 . C15 . C16 . 120.90(13) yes
C14 . C15 . C20 . 120.15(12) yes
C16 . C15 . C20 . 118.94(13) yes
C15 . C16 . C17 . 120.48(14) yes
C15 . C16 . H161 . 118.8 no
C17 . C16 . H161 . 120.8 no
C16 . C17 . C18 . 120.10(14) yes
C16 . C17 . H171 . 120.8 no
C18 . C17 . H171 . 119.1 no
C17 . C18 . C19 . 119.81(13) yes
C17 . C18 . H181 . 120.5 no
C19 . C18 . H181 . 119.7 no
C18 . C19 . C20 . 120.17(14) yes
C18 . C19 . H191 . 120.0 no
C20 . C19 . H191 . 119.8 no
C15 . C20 . C19 . 120.43(13) yes
C15 . C20 . H201 . 120.2 no
C19 . C20 . H201 . 119.3 no
O22 . P21 . O23 . 114.18(5) yes
O22 . P21 . O24 . 111.79(5) yes
O23 . P21 . O24 . 110.17(5) yes
O22 . P21 . O25 . 111.78(5) yes
O23 . P21 . O25 . 104.45(5) yes
O24 . P21 . O25 . 103.74(5) yes
P21 . O24 . H241 . 117.2 no
P21 . O25 . H251 . 112.4 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
C5 . H51 . O25 2_766 149 0.94 2.59 3.4328(19) yes
N6 . H61 . O22 . 171 0.86 2.06 2.9142(19) yes
N1 . H13 . O22 1_554 162 0.92 1.88 2.7683(19) yes
N1 . H12 . O24 2_766 162 0.90 2.00 2.8697(19) yes
N1 . H11 . O22 3_564 147 0.92 2.39 3.2040(19) yes
O24 . H241 . O23 3_565 169 0.82 1.72 2.5342(19) yes
O25 . H251 . O23 4_746 176 0.84 1.76 2.5931(19) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_I_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1585756'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.98740(10)
_cell_length_b                   14.27370(10)
_cell_length_c                   23.21060(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.2783(5)
_cell_angle_gamma                90
_cell_volume                     3640.10(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-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
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C14 H18 Br1 F6 N3 S1 
# Dc =      1.66 Fooo =   1824.00 Mu =     47.36 M =    454.28
# Found Formula = C14 H18 Br1 F6 N3 S1 
# Dc =      1.66 FOOO =   1824.00 Mu =     47.36 M =    454.27

_chemical_formula_sum            'C14 H18 Br1 F6 N3 S1'
_chemical_formula_moiety         'C14 H18 Br1 F6 N3 S1'
_chemical_compound_source        ?
_chemical_formula_weight         454.27


_cell_measurement_reflns_used    37359
_cell_measurement_theta_min      4
_cell_measurement_theta_max      78
_cell_measurement_temperature    160

_exptl_crystal_description       lath
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.057
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_max          0.483

_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1824.000
_exptl_absorpt_coefficient_mu    4.736

# Sheldrick geometric approximatio 0.55 0.76 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.11
_exptl_absorpt_correction_T_max  0.76
_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      160
_diffrn_reflns_number            46471
_reflns_number_total             7149
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 7149 
# Theoretical number of reflections is about 14343 


_diffrn_reflns_theta_min         3.635
_diffrn_reflns_theta_max         72.121
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        72.121
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   2.07
_oxford_diffrn_Wilson_scale      0.41

_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         0.50


# 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         7149
_refine_ls_number_restraints     136
_refine_ls_number_parameters     615
_oxford_refine_ls_R_factor_ref   0.0233
_refine_ls_wR_factor_ref         0.0565
_refine_ls_goodness_of_fit_ref   1.0010
_refine_ls_shift/su_max          0.0025155
_refine_ls_shift/su_mean         0.0000681


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7149
_refine_ls_R_factor_all          0.0233
_refine_ls_wR_factor_all         0.0565

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6871
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_gt          0.0560

# 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 .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    refxyz #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 2.72P] 
 ,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
S1 S 0.62894(3) 0.30617(3) 0.653296(18) 0.0281 1.0000 Uani . . . . . .
C2 C 0.74513(14) 0.24529(11) 0.68121(6) 0.0211 1.0000 Uani D . . . . .
N3 N 0.72782(12) 0.16627(9) 0.71246(6) 0.0246 1.0000 Uani D . . . . .
C4 C 0.61001(14) 0.12072(11) 0.71763(7) 0.0252 1.0000 Uani D . . . . .
C5 C 0.53651(14) 0.16777(11) 0.76511(7) 0.0233 1.0000 Uani D . . . . .
N6 N 0.40504(11) 0.13649(9) 0.76805(6) 0.0222 1.0000 Uani D . . . . .
C7 C 0.34439(15) 0.14532(14) 0.71010(7) 0.0297 1.0000 Uani D . . . . .
C8 C 0.34095(16) 0.19936(13) 0.80978(8) 0.0303 1.0000 Uani D . . . . .
C9 C 0.39494(17) 0.03717(12) 0.78875(8) 0.0318 1.0000 Uani D . . . . .
N10 N 0.86575(12) 0.26665(9) 0.67673(6) 0.0228 1.0000 Uani D . . . . .
C11 C 0.92718(14) 0.34329(11) 0.65298(6) 0.0212 1.0000 Uani D . . . . .
C12 C 0.87560(15) 0.41258(11) 0.61818(7) 0.0237 1.0000 Uani D . . . . .
C13 C 0.94879(15) 0.48531(11) 0.59870(6) 0.0245 1.0000 Uani D . . . . .
C14 C 1.07130(15) 0.49120(11) 0.61194(7) 0.0241 1.0000 Uani D . . . . .
C15 C 1.12184(14) 0.42115(11) 0.64586(7) 0.0231 1.0000 Uani D . . . . .
C16 C 1.05148(14) 0.34783(11) 0.66618(7) 0.0219 1.0000 Uani D . . . . .
C17 C 0.89136(17) 0.56074(12) 0.56284(7) 0.0309 1.0000 Uani . . . . . .
F18 F 0.9557(12) 0.6359(5) 0.5593(7) 0.0904 0.56(2) Uani . . P 1 1 .
F19 F 0.8587(8) 0.5315(5) 0.5127(2) 0.0549 0.56(2) Uani . . P 1 1 .
F20 F 0.7826(8) 0.5859(8) 0.5862(3) 0.0696 0.56(2) Uani . . P 1 1 .
C21 C 1.25426(15) 0.42470(12) 0.66044(8) 0.0304 1.0000 Uani . . . . . .
F22 F 1.29716(11) 0.51169(9) 0.66235(7) 0.0598 1.0000 Uani . . . . . .
F23 F 1.32309(12) 0.37835(13) 0.62395(7) 0.0775 1.0000 Uani . . . . . .
F24 F 1.27955(11) 0.38845(10) 0.71239(6) 0.0565 1.0000 Uani . . . . . .
S31 S 0.86780(4) 0.10055(3) 0.561264(19) 0.0310 1.0000 Uani . . . . . .
C32 C 0.74907(14) 0.03664(12) 0.58308(7) 0.0254 1.0000 Uani D . . . . .
N33 N 0.76129(12) -0.03370(10) 0.62195(6) 0.0289 1.0000 Uani D . . . . .
C34 C 0.87448(15) -0.05358(13) 0.65224(7) 0.0286 1.0000 Uani D . . . . .
C35 C 0.95082(15) -0.12374(12) 0.61855(8) 0.0281 1.0000 Uani D . . . . .
N36 N 1.08475(12) -0.12153(9) 0.63397(6) 0.0233 1.0000 Uani D . . . . .
C37 C 1.10499(17) -0.12889(13) 0.69752(7) 0.0321 1.0000 Uani D . . . . .
C38 C 1.14155(16) -0.03359(13) 0.61179(9) 0.0357 1.0000 Uani D . . . . .
C39 C 1.14443(17) -0.20381(14) 0.60555(9) 0.0368 1.0000 Uani D . . . . .
N40 N 0.63081(12) 0.04586(10) 0.56524(6) 0.0274 1.0000 Uani D . . . . .
C41 C 0.56844(15) 0.12300(11) 0.54160(7) 0.0237 1.0000 Uani D . . . . .
C42 C 0.44234(15) 0.11999(11) 0.54680(7) 0.0253 1.0000 Uani D . . . . .
C43 C 0.37160(15) 0.19493(12) 0.52850(7) 0.0266 1.0000 Uani D . . . . .
C44 C 0.42369(16) 0.27321(12) 0.50350(7) 0.0278 1.0000 Uani D . . . . .
C45 C 0.54911(16) 0.27412(11) 0.49701(7) 0.0267 1.0000 Uani D . . . . .
C46 C 0.62241(15) 0.20091(12) 0.51569(7) 0.0264 1.0000 Uani D . . . . .
C47 C 0.23702(16) 0.19014(13) 0.53840(8) 0.0321 1.0000 Uani D . . . . .
C51 C 0.60564(18) 0.35952(13) 0.47120(9) 0.0375 1.0000 Uani . . . . . .
F52 F 0.5384(6) 0.3965(5) 0.4282(4) 0.0584 0.57(4) Uani . . P 2 1 .
F53 F 0.6082(8) 0.4310(6) 0.5087(3) 0.0521 0.57(4) Uani . . P 2 1 .
F54 F 0.7184(11) 0.3478(10) 0.4552(9) 0.0779 0.57(4) Uani . . P 2 1 .
Br61 Br 0.467385(14) -0.100846(12) 0.648281(8) 0.0272 1.0000 Uani . . . . . .
Br62 Br 1.019301(14) 0.119566(12) 0.761772(7) 0.0261 1.0000 Uani . . . . . .
H121 H 0.7930(13) 0.4093(9) 0.6081(5) 0.0275 1.0000 Uiso D . . . . .
H141 H 1.1183(13) 0.5418(9) 0.5983(5) 0.0274 1.0000 Uiso D . . . . .
H161 H 1.0869(13) 0.3013(9) 0.6896(5) 0.0260 1.0000 Uiso D . . . . .
H41 H 0.6235(14) 0.0541(10) 0.7259(7) 0.0291 1.0000 Uiso D . . . . .
H42 H 0.5660(14) 0.1256(11) 0.6803(6) 0.0288 1.0000 Uiso D . . . . .
H51 H 0.5729(14) 0.1539(11) 0.8027(6) 0.0259 1.0000 Uiso D . . . . .
H52 H 0.5348(14) 0.2345(10) 0.7593(7) 0.0260 1.0000 Uiso D . . . . .
H71 H 0.2579(14) 0.1389(13) 0.7161(7) 0.0430 1.0000 Uiso D . . . . .
H73 H 0.3637(16) 0.2068(11) 0.6942(7) 0.0427 1.0000 Uiso D . . . . .
H72 H 0.3729(16) 0.0955(12) 0.6851(7) 0.0423 1.0000 Uiso D . . . . .
H82 H 0.2572(14) 0.1795(12) 0.8125(8) 0.0434 1.0000 Uiso D . . . . .
H81 H 0.3814(16) 0.1956(13) 0.8467(7) 0.0436 1.0000 Uiso D . . . . .
H83 H 0.3449(17) 0.2627(11) 0.7956(7) 0.0438 1.0000 Uiso D . . . . .
H93 H 0.3093(14) 0.0221(13) 0.7914(8) 0.0458 1.0000 Uiso D . . . . .
H92 H 0.4332(16) 0.0323(13) 0.8269(7) 0.0458 1.0000 Uiso D . . . . .
H91 H 0.4354(16) -0.0047(12) 0.7624(7) 0.0456 1.0000 Uiso D . . . . .
H421 H 0.4064(13) 0.0669(10) 0.5640(4) 0.0294 1.0000 Uiso D . . . . .
H441 H 0.3757(13) 0.3233(10) 0.4921(4) 0.0321 1.0000 Uiso D . . . . .
H461 H 0.7068(13) 0.2037(10) 0.5118(4) 0.0303 1.0000 Uiso D . . . . .
H342 H 0.8552(15) -0.0784(12) 0.6899(7) 0.0341 1.0000 Uiso D . . . . .
H341 H 0.9193(14) 0.0045(11) 0.6581(7) 0.0340 1.0000 Uiso D . . . . .
H352 H 0.9227(15) -0.1871(11) 0.6257(7) 0.0336 1.0000 Uiso D . . . . .
H351 H 0.9444(15) -0.1088(11) 0.5777(6) 0.0331 1.0000 Uiso D . . . . .
H393 H 1.2312(15) -0.1990(13) 0.6118(8) 0.0548 1.0000 Uiso D . . . . .
H391 H 1.1109(17) -0.2594(12) 0.6239(8) 0.0549 1.0000 Uiso D . . . . .
H392 H 1.1260(18) -0.2025(13) 0.5645(7) 0.0545 1.0000 Uiso D . . . . .
H381 H 1.2265(14) -0.0360(13) 0.6210(8) 0.0509 1.0000 Uiso D . . . . .
H382 H 1.1024(17) 0.0192(12) 0.6308(8) 0.0508 1.0000 Uiso D . . . . .
H383 H 1.1278(17) -0.0317(13) 0.5705(7) 0.0509 1.0000 Uiso D . . . . .
H373 H 1.1908(14) -0.1335(13) 0.7054(8) 0.0465 1.0000 Uiso D . . . . .
H371 H 1.0632(16) -0.1846(12) 0.7108(8) 0.0472 1.0000 Uiso D . . . . .
H372 H 1.0731(17) -0.0726(12) 0.7159(7) 0.0468 1.0000 Uiso D . . . . .
H331 H 0.6944(14) -0.0603(13) 0.6346(7) 0.0337 1.0000 Uiso D . . . . .
H101 H 0.9133(13) 0.2272(11) 0.6925(8) 0.0272 1.0000 Uiso D . . . . .
H401 H 0.5824(13) 0.0051(12) 0.5807(8) 0.0327 1.0000 Uiso D . . . . .
H31 H 0.7893(13) 0.1406(11) 0.7290(8) 0.0292 1.0000 Uiso D . . . . .
F153 F 0.579(3) 0.364(2) 0.4150(7) 0.1115 0.43(4) Uani . . P 2 2 .
F120 F 0.8263(17) 0.6210(9) 0.5904(3) 0.0743 0.44(2) Uani . . P 1 2 .
F118 F 0.8307(14) 0.5310(5) 0.5181(5) 0.0665 0.44(2) Uani . . P 1 2 .
F119 F 0.9777(6) 0.6138(7) 0.5355(5) 0.0579 0.44(2) Uani . . P 1 2 .
F152 F 0.5869(17) 0.4349(8) 0.4985(10) 0.0870 0.43(4) Uani . . P 2 2 .
F154 F 0.7267(15) 0.3535(14) 0.4664(10) 0.0601 0.43(4) Uani . . P 2 2 .
F149 F 0.17804(11) 0.26636(10) 0.52174(7) 0.0697 1.0000 Uani . . . . . .
F150 F 0.18624(11) 0.11611(10) 0.51196(5) 0.0503 1.0000 Uani . . . . . .
F148 F 0.20998(9) 0.17840(8) 0.59432(5) 0.0400 1.0000 Uani . . . . . .

_refine_ls_extinction_coef       12.989
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          1.660(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
S1 . C2 . 1.6723(16) yes
C2 . N3 . 1.355(2) yes
C2 . N10 . 1.3643(19) yes
N3 . C4 . 1.4539(19) yes
N3 . H31 . 0.858(14) no
C4 . C5 . 1.525(2) yes
C4 . H41 . 0.981(14) no
C4 . H42 . 0.992(14) no
C5 . N6 . 1.5138(18) yes
C5 . H51 . 0.977(14) no
C5 . H52 . 0.962(14) no
N6 . C7 . 1.503(2) yes
N6 . C8 . 1.499(2) yes
N6 . C9 . 1.501(2) yes
C7 . H71 . 0.966(15) no
C7 . H73 . 0.975(15) no
C7 . H72 . 0.972(15) no
C8 . H82 . 0.965(15) no
C8 . H81 . 0.965(15) no
C8 . H83 . 0.963(15) no
C9 . H93 . 0.968(15) no
C9 . H92 . 0.981(15) no
C9 . H91 . 0.965(15) no
N10 . C11 . 1.3999(19) yes
N10 . H101 . 0.850(14) no
C11 . C12 . 1.395(2) yes
C11 . C16 . 1.400(2) yes
C12 . C13 . 1.390(2) yes
C12 . H121 . 0.938(14) no
C13 . C14 . 1.382(2) yes
C13 . C17 . 1.498(2) yes
C14 . C15 . 1.387(2) yes
C14 . H141 . 0.944(14) no
C15 . C16 . 1.385(2) yes
C15 . C21 . 1.493(2) yes
C16 . H161 . 0.940(14) no
C17 . F18 . 1.287(7) yes
C17 . F19 . 1.286(6) yes
C17 . F20 . 1.363(7) yes
C17 . F120 . 1.290(8) yes
C17 . F118 . 1.301(9) yes
C17 . F119 . 1.372(6) yes
C21 . F22 . 1.329(2) yes
C21 . F23 . 1.317(2) yes
C21 . F24 . 1.340(2) yes
S31 . C32 . 1.6724(16) yes
C32 . N33 . 1.356(2) yes
C32 . N40 . 1.368(2) yes
N33 . C34 . 1.454(2) yes
N33 . H331 . 0.879(15) no
C34 . C35 . 1.524(2) yes
C34 . H342 . 0.967(14) no
C34 . H341 . 0.973(15) no
C35 . N36 . 1.513(2) yes
C35 . H352 . 0.971(14) no
C35 . H351 . 0.974(14) no
N36 . C37 . 1.494(2) yes
N36 . C38 . 1.494(2) yes
N36 . C39 . 1.500(2) yes
C37 . H373 . 0.962(15) no
C37 . H371 . 0.969(15) no
C37 . H372 . 0.975(15) no
C38 . H381 . 0.957(15) no
C38 . H382 . 0.974(16) no
C38 . H383 . 0.971(15) no
C39 . H393 . 0.967(16) no
C39 . H391 . 0.974(16) no
C39 . H392 . 0.973(15) no
N40 . C41 . 1.407(2) yes
N40 . H401 . 0.867(14) no
C41 . C42 . 1.392(2) yes
C41 . C46 . 1.398(2) yes
C42 . C43 . 1.388(2) yes
C42 . H421 . 0.944(14) no
C43 . C44 . 1.384(2) yes
C43 . C47 . 1.499(2) yes
C44 . C45 . 1.387(2) yes
C44 . H441 . 0.926(14) no
C45 . C46 . 1.388(2) yes
C45 . C51 . 1.495(2) yes
C46 . H461 . 0.932(14) no
C47 . F149 . 1.323(2) yes
C47 . F150 . 1.342(2) yes
C47 . F148 . 1.343(2) yes
C51 . F52 . 1.347(6) yes
C51 . F53 . 1.342(7) yes
C51 . F54 . 1.306(12) yes
C51 . F153 . 1.338(10) yes
C51 . F152 . 1.266(11) yes
C51 . F154 . 1.338(16) 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
S1 . C2 . N3 . 122.08(12) yes
S1 . C2 . N10 . 126.47(12) yes
N3 . C2 . N10 . 111.46(13) yes
C2 . N3 . C4 . 122.94(14) yes
C2 . N3 . H31 . 118.9(10) no
C4 . N3 . H31 . 118.2(10) no
N3 . C4 . C5 . 109.72(13) yes
N3 . C4 . H41 . 108.4(9) no
C5 . C4 . H41 . 111.4(9) no
N3 . C4 . H42 . 109.1(9) no
C5 . C4 . H42 . 110.0(9) no
H41 . C4 . H42 . 108.2(12) no
C4 . C5 . N6 . 114.29(13) yes
C4 . C5 . H51 . 109.8(9) no
N6 . C5 . H51 . 106.7(9) no
C4 . C5 . H52 . 110.2(9) no
N6 . C5 . H52 . 106.3(9) no
H51 . C5 . H52 . 109.4(12) no
C5 . N6 . C7 . 110.72(12) yes
C5 . N6 . C8 . 107.69(12) yes
C7 . N6 . C8 . 108.69(13) yes
C5 . N6 . C9 . 111.41(12) yes
C7 . N6 . C9 . 109.41(13) yes
C8 . N6 . C9 . 108.84(13) yes
N6 . C7 . H71 . 107.2(10) no
N6 . C7 . H73 . 108.5(10) no
H71 . C7 . H73 . 110.8(13) no
N6 . C7 . H72 . 109.3(11) no
H71 . C7 . H72 . 109.7(13) no
H73 . C7 . H72 . 111.2(13) no
N6 . C8 . H82 . 108.5(10) no
N6 . C8 . H81 . 109.0(10) no
H82 . C8 . H81 . 111.2(13) no
N6 . C8 . H83 . 108.7(11) no
H82 . C8 . H83 . 110.0(13) no
H81 . C8 . H83 . 109.5(13) no
N6 . C9 . H93 . 107.7(11) no
N6 . C9 . H92 . 108.9(11) no
H93 . C9 . H92 . 109.8(13) no
N6 . C9 . H91 . 110.3(11) no
H93 . C9 . H91 . 110.8(13) no
H92 . C9 . H91 . 109.4(13) no
C2 . N10 . C11 . 132.45(14) yes
C2 . N10 . H101 . 114.4(10) no
C11 . N10 . H101 . 113.0(10) no
N10 . C11 . C12 . 125.91(14) yes
N10 . C11 . C16 . 114.95(14) yes
C12 . C11 . C16 . 119.14(14) yes
C11 . C12 . C13 . 118.92(15) yes
C11 . C12 . H121 . 119.9(9) no
C13 . C12 . H121 . 121.1(9) no
C12 . C13 . C14 . 122.52(15) yes
C12 . C13 . C17 . 118.33(15) yes
C14 . C13 . C17 . 119.14(15) yes
C13 . C14 . C15 . 117.98(14) yes
C13 . C14 . H141 . 120.5(9) no
C15 . C14 . H141 . 121.6(9) no
C14 . C15 . C16 . 121.02(15) yes
C14 . C15 . C21 . 119.42(14) yes
C16 . C15 . C21 . 119.56(15) yes
C11 . C16 . C15 . 120.40(15) yes
C11 . C16 . H161 . 119.6(9) no
C15 . C16 . H161 . 120.0(9) no
C13 . C17 . F18 . 113.8(3) yes
C13 . C17 . F19 . 112.6(4) yes
F18 . C17 . F19 . 111.4(6) yes
C13 . C17 . F20 . 109.6(3) yes
F18 . C17 . F20 . 106.8(4) yes
F19 . C17 . F20 . 101.8(5) yes
C13 . C17 . F120 . 115.9(4) yes
C13 . C17 . F118 . 114.9(4) yes
F120 . C17 . F118 . 109.2(6) yes
C13 . C17 . F119 . 111.3(3) yes
F120 . C17 . F119 . 104.3(6) yes
F118 . C17 . F119 . 99.4(5) yes
C15 . C21 . F22 . 112.60(15) yes
C15 . C21 . F23 . 113.53(15) yes
F22 . C21 . F23 . 106.63(16) yes
C15 . C21 . F24 . 112.86(14) yes
F22 . C21 . F24 . 105.01(15) yes
F23 . C21 . F24 . 105.52(16) yes
S31 . C32 . N33 . 122.04(12) yes
S31 . C32 . N40 . 126.65(13) yes
N33 . C32 . N40 . 111.31(14) yes
C32 . N33 . C34 . 123.23(14) yes
C32 . N33 . H331 . 117.5(10) no
C34 . N33 . H331 . 118.0(10) no
N33 . C34 . C35 . 110.59(14) yes
N33 . C34 . H342 . 108.5(10) no
C35 . C34 . H342 . 110.2(10) no
N33 . C34 . H341 . 109.4(10) no
C35 . C34 . H341 . 110.6(10) no
H342 . C34 . H341 . 107.4(12) no
C34 . C35 . N36 . 113.70(14) yes
C34 . C35 . H352 . 110.4(10) no
N36 . C35 . H352 . 106.8(10) no
C34 . C35 . H351 . 108.5(10) no
N36 . C35 . H351 . 106.9(10) no
H352 . C35 . H351 . 110.4(12) no
C35 . N36 . C37 . 111.83(13) yes
C35 . N36 . C38 . 110.08(13) yes
C37 . N36 . C38 . 109.79(14) yes
C35 . N36 . C39 . 107.85(13) yes
C37 . N36 . C39 . 108.41(13) yes
C38 . N36 . C39 . 108.78(14) yes
N36 . C37 . H373 . 109.4(11) no
N36 . C37 . H371 . 107.7(11) no
H373 . C37 . H371 . 110.4(13) no
N36 . C37 . H372 . 108.8(11) no
H373 . C37 . H372 . 109.1(13) no
H371 . C37 . H372 . 111.4(13) no
N36 . C38 . H381 . 107.6(11) no
N36 . C38 . H382 . 107.9(11) no
H381 . C38 . H382 . 110.9(13) no
N36 . C38 . H383 . 107.5(11) no
H381 . C38 . H383 . 111.6(13) no
H382 . C38 . H383 . 111.1(13) no
N36 . C39 . H393 . 108.2(11) no
N36 . C39 . H391 . 106.2(11) no
H393 . C39 . H391 . 111.5(13) no
N36 . C39 . H392 . 109.0(11) no
H393 . C39 . H392 . 110.3(13) no
H391 . C39 . H392 . 111.5(13) no
C32 . N40 . C41 . 130.80(14) yes
C32 . N40 . H401 . 113.2(10) no
C41 . N40 . H401 . 112.8(10) no
N40 . C41 . C42 . 115.17(14) yes
N40 . C41 . C46 . 125.70(15) yes
C42 . C41 . C46 . 119.10(15) yes
C41 . C42 . C43 . 120.40(15) yes
C41 . C42 . H421 . 118.7(9) no
C43 . C42 . H421 . 120.9(9) no
C42 . C43 . C44 . 121.22(15) yes
C42 . C43 . C47 . 118.00(15) yes
C44 . C43 . C47 . 120.74(15) yes
C43 . C44 . C45 . 117.78(15) yes
C43 . C44 . H441 . 120.5(9) no
C45 . C44 . H441 . 121.7(9) no
C44 . C45 . C46 . 122.31(15) yes
C44 . C45 . C51 . 117.79(15) yes
C46 . C45 . C51 . 119.85(16) yes
C41 . C46 . C45 . 119.14(15) yes
C41 . C46 . H461 . 120.0(9) no
C45 . C46 . H461 . 120.8(9) no
C43 . C47 . F149 . 113.57(14) yes
C43 . C47 . F150 . 111.96(15) yes
F149 . C47 . F150 . 108.17(15) yes
C43 . C47 . F148 . 112.13(14) yes
F149 . C47 . F148 . 105.94(16) yes
F150 . C47 . F148 . 104.49(14) yes
C45 . C51 . F52 . 112.9(3) yes
C45 . C51 . F53 . 111.5(4) yes
F52 . C51 . F53 . 101.1(5) yes
C45 . C51 . F54 . 114.0(6) yes
F52 . C51 . F54 . 110.9(8) yes
F53 . C51 . F54 . 105.4(8) yes
C45 . C51 . F153 . 109.8(6) yes
C45 . C51 . F152 . 115.1(6) yes
F153 . C51 . F152 . 114.3(11) yes
C45 . C51 . F154 . 113.3(9) yes
F153 . C51 . F154 . 97.9(17) yes
F152 . C51 . F154 . 105.1(11) yes


_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_mb170814_9bv6_benz_G5_2
_database_code_depnum_ccdc_archive 'CCDC 1585755'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H48.70 N4 O11.35'
_chemical_formula_weight         743.11

# start Validation Reply Form
_vrf_PLAT430_mb170814_9bv6_benz_G5_2 
;
PROBLEM: Short Inter D...A Contact O27 ..O110 . 2.58 Ang.
RESPONSE: O110 is only partially occupied and therefore no hydrogen
atoms of this water molecule could be found.
;
# end Validation Reply Form

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.81000(10)
_cell_length_b                   9.7133(2)
_cell_length_c                   21.7147(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.1689(16)
_cell_angle_gamma                90
_cell_volume                     1829.03(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    16550
_cell_measurement_theta_min      4.124
_cell_measurement_theta_max      78.601

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             791
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.007
_exptl_absorpt_coefficient_mu    0.830
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27e (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31303
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.137
_diffrn_reflns_theta_max         74.489
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7406
_reflns_number_gt                6788
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Rigaku, 2015)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku, 2015)'
_computing_data_reduction        'CrysAlis PRO (Rigaku, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+0.3780P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2927 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(8)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         7406
_refine_ls_number_parameters     526
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4148(3) 0.5004(2) 0.42412(10) 0.0367(5) Uani 1 1 d . . . . .
C2 C 0.3464(3) 0.5237(3) 0.36288(13) 0.0300(6) Uani 1 1 d . . . . .
C3 C 0.4037(4) 0.6110(3) 0.32282(13) 0.0311(6) Uani 1 1 d . . . . .
H3 H 0.4974 0.6598 0.3359 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3190(4) 0.6260(3) 0.26168(13) 0.0308(6) Uani 1 1 d . . . . .
C5 C 0.1789(3) 0.5541(3) 0.24394(14) 0.0308(6) Uani 1 1 d . . . . .
N6 N 0.1204(3) 0.5889(3) 0.18307(12) 0.0352(6) Uani 1 1 d . . . . .
H6 H 0.0335 0.5580 0.1612 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2172(4) 0.6780(3) 0.16215(15) 0.0419(8) Uani 1 1 d . . . . .
H7 H 0.2012 0.7169 0.1214 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3421(4) 0.7045(4) 0.20814(15) 0.0409(8) Uani 1 1 d D . . . .
C12 C 0.1243(3) 0.4629(4) 0.28447(15) 0.0356(7) Uani 1 1 d . . . . .
H12 H 0.0315 0.4127 0.2717 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2096(4) 0.4480(4) 0.34358(15) 0.0357(7) Uani 1 1 d . . . . .
H13 H 0.1756 0.3856 0.3720 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5404(3) 0.5892(3) 0.44962(14) 0.0321(6) Uani 1 1 d . . . . .
H14A H 0.5062 0.6864 0.4472 0.039 Uiso 1 1 calc R U . . .
H14B H 0.6259 0.5792 0.4258 0.039 Uiso 1 1 calc R U . . .
C15 C 0.5935(3) 0.5478(3) 0.51692(14) 0.0309(6) Uani 1 1 d . . . . .
C16 C 0.5507(4) 0.6236(4) 0.56517(15) 0.0392(7) Uani 1 1 d . . . . .
H16 H 0.4892 0.7038 0.5559 0.047 Uiso 1 1 calc R U . . .
C17 C 0.5970(4) 0.5830(4) 0.62710(16) 0.0449(8) Uani 1 1 d . . . . .
H17 H 0.5682 0.6358 0.6600 0.054 Uiso 1 1 calc R U . . .
C18 C 0.6847(4) 0.4658(4) 0.64043(16) 0.0447(8) Uani 1 1 d . . . . .
H18 H 0.7138 0.4365 0.6826 0.054 Uiso 1 1 calc R U . . .
C19 C 0.7307(4) 0.3909(4) 0.59310(16) 0.0411(7) Uani 1 1 d . . . . .
H19 H 0.7920 0.3106 0.6026 0.049 Uiso 1 1 calc R U . . .
C20 C 0.6868(4) 0.4333(3) 0.53123(15) 0.0349(6) Uani 1 1 d . . . . .
H20 H 0.7212 0.3834 0.4986 0.042 Uiso 1 1 calc R U . . .
O21 O 0.5723(2) 0.4348(2) 0.04138(10) 0.0319(4) Uani 1 1 d . . . . .
H21 H 0.5310 0.3612 0.0266 0.048 Uiso 1 1 calc R U . . .
C22 C 0.6709(3) 0.4850(3) 0.00201(13) 0.0258(5) Uani 1 1 d . . . . .
H22 H 0.6718 0.4190 -0.0333 0.031 Uiso 1 1 calc R U . . .
C23 C 0.8358(3) 0.5005(3) 0.03949(12) 0.0254(5) Uani 1 1 d . . . . .
H23 H 0.9050 0.5349 0.0110 0.030 Uiso 1 1 calc R U . . .
O24 O 0.8400(3) 0.5945(2) 0.08987(10) 0.0332(5) Uani 1 1 d . . . . .
H24 H 0.8425 0.6754 0.0765 0.050 Uiso 1 1 calc R U . . .
C25 C 0.8931(3) 0.3581(3) 0.06506(14) 0.0318(6) Uani 1 1 d . . . . .
O26 O 0.8980(2) 0.2667(2) 0.02410(11) 0.0354(5) Uani 1 1 d . . . . .
O27 O 0.9327(4) 0.3416(3) 0.12207(11) 0.0555(7) Uani 1 1 d . . . . .
C28 C 0.6160(3) 0.6258(3) -0.02429(15) 0.0312(6) Uani 1 1 d . . . . .
O29 O 0.6667(3) 0.6648(2) -0.07177(11) 0.0407(5) Uani 1 1 d . . . . .
O30 O 0.5299(3) 0.6936(3) 0.00526(16) 0.0602(8) Uani 1 1 d . . . . .
O31 O -0.0869(3) 0.2756(2) 0.42322(10) 0.0353(5) Uani 1 1 d . . . . .
C32 C -0.1528(3) 0.2474(3) 0.36216(14) 0.0301(6) Uani 1 1 d . . . . .
C33 C -0.0954(3) 0.1544(3) 0.32411(13) 0.0271(6) Uani 1 1 d . . . . .
H33 H -0.0025 0.1057 0.3387 0.032 Uiso 1 1 calc R U . . .
C34 C -0.1773(3) 0.1334(3) 0.26335(13) 0.0280(6) Uani 1 1 d . . . . .
C35 C -0.3158(3) 0.2058(3) 0.24232(14) 0.0349(7) Uani 1 1 d . . . . .
N36 N -0.3724(3) 0.1611(3) 0.18251(12) 0.0405(7) Uani 1 1 d . . . . .
H36 H -0.4585 0.1896 0.1591 0.049 Uiso 1 1 calc R U . . .
C37 C -0.2743(4) 0.0658(3) 0.16515(14) 0.0345(7) Uani 1 1 d . . . . .
H37 H -0.2879 0.0208 0.1257 0.041 Uiso 1 1 calc R U . . .
C38 C -0.1527(3) 0.0447(3) 0.21337(13) 0.0274(6) Uani 1 1 d . . . . .
C39 C -0.0133(3) -0.0438(3) 0.21323(13) 0.0298(6) Uani 1 1 d . . . . .
H39A H -0.0411 -0.1210 0.1836 0.036 Uiso 1 1 calc R U . . .
H39B H 0.0195 -0.0835 0.2555 0.036 Uiso 1 1 calc R U . . .
C40 C 0.1209(3) 0.0354(3) 0.19485(13) 0.0306(6) Uani 1 1 d . . . . .
H40A H 0.1466 0.1152 0.2231 0.037 Uiso 1 1 calc R U . . .
H40B H 0.2128 -0.0249 0.1992 0.037 Uiso 1 1 calc R U . . .
N41 N 0.0796(3) 0.0842(3) 0.12898(12) 0.0307(5) Uani 1 1 d . . . . .
H41A H 0.030(5) 0.017(5) 0.1034(19) 0.046 Uiso 1 1 d . U . . .
H41B H 0.028(5) 0.164(5) 0.121(2) 0.046 Uiso 1 1 d . U . . .
H41C H 0.167(5) 0.102(5) 0.1115(19) 0.046 Uiso 1 1 d . U . . .
C42 C -0.3719(4) 0.3021(4) 0.28096(16) 0.0417(8) Uani 1 1 d . . . . .
H42 H -0.4639 0.3523 0.2666 0.050 Uiso 1 1 calc R U . . .
C43 C -0.2897(4) 0.3216(4) 0.34019(15) 0.0387(7) Uani 1 1 d . . . . .
H43 H -0.3257 0.3865 0.3670 0.046 Uiso 1 1 calc R U . . .
C44 C 0.0365(3) 0.1849(3) 0.45059(14) 0.0314(6) Uani 1 1 d . . . . .
H44A H 0.1230 0.1910 0.4272 0.038 Uiso 1 1 calc R U . . .
H44B H -0.0004 0.0885 0.4489 0.038 Uiso 1 1 calc R U . . .
C45 C 0.0893(3) 0.2282(3) 0.51733(13) 0.0293(6) Uani 1 1 d . . . . .
C46 C 0.1864(3) 0.3422(3) 0.53137(14) 0.0326(6) Uani 1 1 d . . . . .
H46 H 0.2188 0.3924 0.4984 0.039 Uiso 1 1 calc R U . . .
C47 C 0.2353(4) 0.3823(3) 0.59247(15) 0.0369(7) Uani 1 1 d . . . . .
H47 H 0.3006 0.4603 0.6015 0.044 Uiso 1 1 calc R U . . .
C48 C 0.1893(4) 0.3087(4) 0.64097(15) 0.0382(7) Uani 1 1 d . . . . .
H48 H 0.2213 0.3375 0.6831 0.046 Uiso 1 1 calc R U . . .
C49 C 0.0976(4) 0.1944(4) 0.62786(16) 0.0435(8) Uani 1 1 d . . . . .
H49 H 0.0687 0.1425 0.6610 0.052 Uiso 1 1 calc R U . . .
C50 C 0.0470(4) 0.1544(4) 0.56630(15) 0.0385(7) Uani 1 1 d . . . . .
H50 H -0.0173 0.0757 0.5576 0.046 Uiso 1 1 calc R U . . .
O51 O 0.0729(3) 0.3476(2) -0.05760(10) 0.0349(5) Uani 1 1 d . . . . .
H51A H 0.136(5) 0.401(5) -0.036(2) 0.052 Uiso 1 1 d . U . . .
H51B H 0.020(5) 0.323(5) -0.024(2) 0.052 Uiso 1 1 d . U . . .
O52 O 0.3594(3) 0.3774(3) 0.15220(12) 0.0437(6) Uani 1 1 d . . . . .
H52A H 0.331(6) 0.329(6) 0.114(2) 0.066 Uiso 1 1 d . U . . .
H52B H 0.278(6) 0.407(6) 0.158(2) 0.066 Uiso 1 1 d . U . . .
O53 O 0.2514(3) 0.5266(3) 0.01425(13) 0.0427(5) Uani 1 1 d . . . . .
H53A H 0.326(6) 0.527(6) 0.004(2) 0.064 Uiso 1 1 d . U . . .
H53B H 0.226(6) 0.614(6) -0.005(2) 0.064 Uiso 1 1 d . U . . .
C90 C 0.4685(6) 0.7944(5) 0.2010(2) 0.0310(11) Uani 0.695(10) 1 d . U P A 1
H90A H 0.4924 0.8571 0.2373 0.037 Uiso 0.695(10) 1 calc R U P A 1
H90B H 0.4409 0.8507 0.1626 0.037 Uiso 0.695(10) 1 calc R U P A 1
C100 C 0.6073(6) 0.7039(6) 0.1965(2) 0.0313(13) Uani 0.695(10) 1 d . U P A 1
H10A H 0.6955 0.7628 0.1909 0.038 Uiso 0.695(10) 1 calc R U P A 1
H10B H 0.6369 0.6520 0.2361 0.038 Uiso 0.695(10) 1 calc R U P A 1
N110 N 0.5736(4) 0.6047(4) 0.14320(17) 0.0324(12) Uani 0.695(10) 1 d . U P A 1
H11A H 0.4967 0.5467 0.1495 0.049 Uiso 0.695(10) 1 calc R U P A 1
H11B H 0.6599 0.5552 0.1407 0.049 Uiso 0.695(10) 1 calc R U P A 1
H11C H 0.5436 0.6520 0.1069 0.049 Uiso 0.695(10) 1 calc R U P A 1
O110 O 0.807(2) 0.461(2) 0.2065(10) 0.159(7) Uiso 0.348(5) 1 d . . P A 1
C91 C 0.5185(12) 0.7475(14) 0.1999(5) 0.028(3) Uiso 0.305(10) 1 d D U P A 2
H91A H 0.5109 0.7874 0.1575 0.034 Uiso 0.305(10) 1 calc R U P A 2
H91B H 0.5517 0.8229 0.2299 0.034 Uiso 0.305(10) 1 calc R U P A 2
C101 C 0.6525(14) 0.6403(14) 0.2079(6) 0.036(3) Uiso 0.305(10) 1 d D U P A 2
H10C H 0.7483 0.6868 0.2013 0.043 Uiso 0.305(10) 1 calc R U P A 2
H10D H 0.6697 0.6044 0.2513 0.043 Uiso 0.305(10) 1 calc R U P A 2
N111 N 0.6202(12) 0.5230(12) 0.1635(5) 0.041(3) Uiso 0.305(10) 1 d . U P A 2
H11D H 0.5357 0.4764 0.1711 0.062 Uiso 0.305(10) 1 calc R U P A 2
H11E H 0.7029 0.4653 0.1688 0.062 Uiso 0.305(10) 1 calc R U P A 2
H11F H 0.6022 0.5555 0.1236 0.062 Uiso 0.305(10) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.378(3) . ?
O1 C14 1.435(4) . ?
C2 C3 1.373(4) . ?
C2 C13 1.411(4) . ?
C3 C4 1.411(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(4) . ?
C4 C8 1.434(4) . ?
C5 N6 1.373(4) . ?
C5 C12 1.393(5) . ?
N6 C7 1.348(5) . ?
N6 H6 0.8800 . ?
C7 C8 1.374(5) . ?
C7 H7 0.9500 . ?
C8 C90 1.445(6) . ?
C8 C91 1.649(10) . ?
C12 C13 1.375(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.508(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C20 1.386(5) . ?
C15 C16 1.386(4) . ?
C16 C17 1.392(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
O21 C22 1.409(3) . ?
O21 H21 0.8400 . ?
C22 C28 1.527(4) . ?
C22 C23 1.542(4) . ?
C22 H22 1.0000 . ?
C23 O24 1.420(3) . ?
C23 C25 1.541(4) . ?
C23 H23 1.0000 . ?
O24 H24 0.8400 . ?
C25 O27 1.236(4) . ?
C25 O26 1.263(4) . ?
C28 O29 1.253(4) . ?
C28 O30 1.262(4) . ?
O31 C32 1.378(4) . ?
O31 C44 1.443(4) . ?
C32 C33 1.379(4) . ?
C32 C43 1.414(4) . ?
C33 C34 1.403(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.413(4) . ?
C34 C38 1.432(4) . ?
C35 N36 1.377(4) . ?
C35 C42 1.403(5) . ?
N36 C37 1.365(4) . ?
N36 H36 0.8800 . ?
C37 C38 1.375(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.499(4) . ?
C39 C40 1.522(4) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 N41 1.490(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
N41 H41A 0.92(5) . ?
N41 H41B 0.90(5) . ?
N41 H41C 0.93(4) . ?
C42 C43 1.373(5) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C45 1.502(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C50 1.387(5) . ?
C45 C46 1.400(4) . ?
C46 C47 1.377(4) . ?
C46 H46 0.9500 . ?
C47 C48 1.391(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.374(5) . ?
C48 H48 0.9500 . ?
C49 C50 1.388(5) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
O51 H51A 0.84(5) . ?
O51 H51B 0.96(5) . ?
O52 H52A 0.94(5) . ?
O52 H52B 0.80(6) . ?
O53 H53A 0.73(5) . ?
O53 H53B 0.95(6) . ?
C90 C100 1.523(7) . ?
C90 H90A 0.9900 . ?
C90 H90B 0.9900 . ?
C100 N110 1.495(6) . ?
C100 H10A 0.9900 . ?
C100 H10B 0.9900 . ?
N110 H11A 0.9100 . ?
N110 H11B 0.9100 . ?
N110 H11C 0.9100 . ?
C91 C101 1.561(11) . ?
C91 H91A 0.9900 . ?
C91 H91B 0.9900 . ?
C101 N111 1.486(15) . ?
C101 H10C 0.9900 . ?
C101 H10D 0.9900 . ?
N111 H11D 0.9100 . ?
N111 H11E 0.9100 . ?
N111 H11F 0.9100 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C14 116.7(2) . . ?
C3 C2 O1 124.5(3) . . ?
C3 C2 C13 121.6(3) . . ?
O1 C2 C13 113.9(3) . . ?
C2 C3 C4 117.9(3) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 C8 133.7(3) . . ?
C5 C4 C8 106.5(3) . . ?
N6 C5 C12 130.7(3) . . ?
N6 C5 C4 107.6(3) . . ?
C12 C5 C4 121.7(3) . . ?
C7 N6 C5 109.3(3) . . ?
C7 N6 H6 125.4 . . ?
C5 N6 H6 125.4 . . ?
N6 C7 C8 110.4(3) . . ?
N6 C7 H7 124.8 . . ?
C8 C7 H7 124.8 . . ?
C7 C8 C4 106.2(3) . . ?
C7 C8 C90 124.7(3) . . ?
C4 C8 C90 129.1(3) . . ?
C7 C8 C91 128.2(5) . . ?
C4 C8 C91 119.6(5) . . ?
C13 C12 C5 117.7(3) . . ?
C13 C12 H12 121.2 . . ?
C5 C12 H12 121.2 . . ?
C12 C13 C2 121.3(3) . . ?
C12 C13 H13 119.4 . . ?
C2 C13 H13 119.4 . . ?
O1 C14 C15 107.4(2) . . ?
O1 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O1 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C20 C15 C16 119.1(3) . . ?
C20 C15 C14 120.1(3) . . ?
C16 C15 C14 120.8(3) . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 120.4(3) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 O21 H21 109.5 . . ?
O21 C22 C28 110.4(2) . . ?
O21 C22 C23 109.7(2) . . ?
C28 C22 C23 108.5(2) . . ?
O21 C22 H22 109.4 . . ?
C28 C22 H22 109.4 . . ?
C23 C22 H22 109.4 . . ?
O24 C23 C25 109.7(2) . . ?
O24 C23 C22 111.3(2) . . ?
C25 C23 C22 108.7(2) . . ?
O24 C23 H23 109.0 . . ?
C25 C23 H23 109.0 . . ?
C22 C23 H23 109.0 . . ?
C23 O24 H24 109.5 . . ?
O27 C25 O26 125.1(3) . . ?
O27 C25 C23 119.6(3) . . ?
O26 C25 C23 115.3(2) . . ?
O29 C28 O30 126.4(3) . . ?
O29 C28 C22 116.3(2) . . ?
O30 C28 C22 117.2(3) . . ?
C32 O31 C44 115.7(2) . . ?
O31 C32 C33 124.7(3) . . ?
O31 C32 C43 114.4(3) . . ?
C33 C32 C43 120.9(3) . . ?
C32 C33 C34 118.4(3) . . ?
C32 C33 H33 120.8 . . ?
C34 C33 H33 120.8 . . ?
C33 C34 C35 120.2(3) . . ?
C33 C34 C38 132.7(3) . . ?
C35 C34 C38 107.0(2) . . ?
N36 C35 C42 131.8(3) . . ?
N36 C35 C34 107.2(3) . . ?
C42 C35 C34 120.9(3) . . ?
C37 N36 C35 109.5(3) . . ?
C37 N36 H36 125.3 . . ?
C35 N36 H36 125.3 . . ?
N36 C37 C38 109.7(3) . . ?
N36 C37 H37 125.2 . . ?
C38 C37 H37 125.2 . . ?
C37 C38 C34 106.6(3) . . ?
C37 C38 C39 127.7(3) . . ?
C34 C38 C39 125.5(2) . . ?
C38 C39 C40 112.7(2) . . ?
C38 C39 H39A 109.1 . . ?
C40 C39 H39A 109.1 . . ?
C38 C39 H39B 109.1 . . ?
C40 C39 H39B 109.1 . . ?
H39A C39 H39B 107.8 . . ?
N41 C40 C39 110.1(2) . . ?
N41 C40 H40A 109.6 . . ?
C39 C40 H40A 109.6 . . ?
N41 C40 H40B 109.6 . . ?
C39 C40 H40B 109.6 . . ?
H40A C40 H40B 108.2 . . ?
C40 N41 H41A 111(3) . . ?
C40 N41 H41B 119(3) . . ?
H41A N41 H41B 109(4) . . ?
C40 N41 H41C 112(2) . . ?
H41A N41 H41C 103(4) . . ?
H41B N41 H41C 101(4) . . ?
C43 C42 C35 117.9(3) . . ?
C43 C42 H42 121.0 . . ?
C35 C42 H42 121.0 . . ?
C42 C43 C32 121.6(3) . . ?
C42 C43 H43 119.2 . . ?
C32 C43 H43 119.2 . . ?
O31 C44 C45 108.0(2) . . ?
O31 C44 H44A 110.1 . . ?
C45 C44 H44A 110.1 . . ?
O31 C44 H44B 110.1 . . ?
C45 C44 H44B 110.1 . . ?
H44A C44 H44B 108.4 . . ?
C50 C45 C46 118.6(3) . . ?
C50 C45 C44 121.1(3) . . ?
C46 C45 C44 120.3(3) . . ?
C47 C46 C45 120.6(3) . . ?
C47 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
C46 C47 C48 120.0(3) . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
C49 C48 C47 119.9(3) . . ?
C49 C48 H48 120.1 . . ?
C47 C48 H48 120.1 . . ?
C48 C49 C50 120.2(3) . . ?
C48 C49 H49 119.9 . . ?
C50 C49 H49 119.9 . . ?
C45 C50 C49 120.7(3) . . ?
C45 C50 H50 119.7 . . ?
C49 C50 H50 119.7 . . ?
H51A O51 H51B 95(4) . . ?
H52A O52 H52B 102(5) . . ?
H53A O53 H53B 91(5) . . ?
C8 C90 C100 107.5(4) . . ?
C8 C90 H90A 110.2 . . ?
C100 C90 H90A 110.2 . . ?
C8 C90 H90B 110.2 . . ?
C100 C90 H90B 110.2 . . ?
H90A C90 H90B 108.5 . . ?
N110 C100 C90 111.7(4) . . ?
N110 C100 H10A 109.3 . . ?
C90 C100 H10A 109.3 . . ?
N110 C100 H10B 109.3 . . ?
C90 C100 H10B 109.3 . . ?
H10A C100 H10B 107.9 . . ?
C100 N110 H11A 109.5 . . ?
C100 N110 H11B 109.5 . . ?
H11A N110 H11B 109.5 . . ?
C100 N110 H11C 109.5 . . ?
H11A N110 H11C 109.5 . . ?
H11B N110 H11C 109.5 . . ?
C101 C91 C8 121.8(8) . . ?
C101 C91 H91A 106.9 . . ?
C8 C91 H91A 106.9 . . ?
C101 C91 H91B 106.9 . . ?
C8 C91 H91B 106.9 . . ?
H91A C91 H91B 106.7 . . ?
N111 C101 C91 112.6(10) . . ?
N111 C101 H10C 109.1 . . ?
C91 C101 H10C 109.1 . . ?
N111 C101 H10D 109.1 . . ?
C91 C101 H10D 109.1 . . ?
H10C C101 H10D 107.8 . . ?
C101 N111 H11D 109.5 . . ?
C101 N111 H11E 109.5 . . ?
H11D N111 H11E 109.5 . . ?
C101 N111 H11F 109.5 . . ?
H11D N111 H11F 109.5 . . ?
H11E N111 H11F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O1 C2 C3 9.8(4) . . . . ?
C14 O1 C2 C13 -170.7(3) . . . . ?
O1 C2 C3 C4 -178.9(3) . . . . ?
C13 C2 C3 C4 1.7(5) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C2 C3 C4 C8 -179.4(3) . . . . ?
C3 C4 C5 N6 179.1(3) . . . . ?
C8 C4 C5 N6 -0.6(3) . . . . ?
C3 C4 C5 C12 -2.9(4) . . . . ?
C8 C4 C5 C12 177.4(3) . . . . ?
C12 C5 N6 C7 -177.5(3) . . . . ?
C4 C5 N6 C7 0.3(3) . . . . ?
C5 N6 C7 C8 0.2(4) . . . . ?
N6 C7 C8 C4 -0.5(4) . . . . ?
N6 C7 C8 C90 179.3(4) . . . . ?
N6 C7 C8 C91 151.5(7) . . . . ?
C3 C4 C8 C7 -178.9(3) . . . . ?
C5 C4 C8 C7 0.7(4) . . . . ?
C3 C4 C8 C90 1.2(7) . . . . ?
C5 C4 C8 C90 -179.1(4) . . . . ?
C3 C4 C8 C91 26.1(7) . . . . ?
C5 C4 C8 C91 -154.2(6) . . . . ?
N6 C5 C12 C13 179.4(3) . . . . ?
C4 C5 C12 C13 1.9(5) . . . . ?
C5 C12 C13 C2 0.8(5) . . . . ?
C3 C2 C13 C12 -2.7(5) . . . . ?
O1 C2 C13 C12 177.8(3) . . . . ?
C2 O1 C14 C15 178.3(2) . . . . ?
O1 C14 C15 C20 78.9(3) . . . . ?
O1 C14 C15 C16 -101.5(3) . . . . ?
C20 C15 C16 C17 -1.9(5) . . . . ?
C14 C15 C16 C17 178.5(3) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C16 C17 C18 C19 1.9(5) . . . . ?
C17 C18 C19 C20 -0.6(5) . . . . ?
C16 C15 C20 C19 3.2(5) . . . . ?
C14 C15 C20 C19 -177.2(3) . . . . ?
C18 C19 C20 C15 -2.0(5) . . . . ?
O21 C22 C23 O24 -60.4(3) . . . . ?
C28 C22 C23 O24 60.2(3) . . . . ?
O21 C22 C23 C25 60.5(3) . . . . ?
C28 C22 C23 C25 -178.9(2) . . . . ?
O24 C23 C25 O27 0.4(4) . . . . ?
C22 C23 C25 O27 -121.5(3) . . . . ?
O24 C23 C25 O26 -178.3(2) . . . . ?
C22 C23 C25 O26 59.8(3) . . . . ?
O21 C22 C28 O29 -161.7(3) . . . . ?
C23 C22 C28 O29 78.1(3) . . . . ?
O21 C22 C28 O30 21.4(4) . . . . ?
C23 C22 C28 O30 -98.9(3) . . . . ?
C44 O31 C32 C33 -9.8(4) . . . . ?
C44 O31 C32 C43 169.5(3) . . . . ?
O31 C32 C33 C34 178.2(3) . . . . ?
C43 C32 C33 C34 -1.0(5) . . . . ?
C32 C33 C34 C35 -0.4(4) . . . . ?
C32 C33 C34 C38 -178.5(3) . . . . ?
C33 C34 C35 N36 -178.0(3) . . . . ?
C38 C34 C35 N36 0.6(3) . . . . ?
C33 C34 C35 C42 1.6(5) . . . . ?
C38 C34 C35 C42 -179.9(3) . . . . ?
C42 C35 N36 C37 179.7(4) . . . . ?
C34 C35 N36 C37 -0.9(4) . . . . ?
C35 N36 C37 C38 0.8(4) . . . . ?
N36 C37 C38 C34 -0.4(4) . . . . ?
N36 C37 C38 C39 -175.6(3) . . . . ?
C33 C34 C38 C37 178.2(3) . . . . ?
C35 C34 C38 C37 -0.2(3) . . . . ?
C33 C34 C38 C39 -6.4(5) . . . . ?
C35 C34 C38 C39 175.2(3) . . . . ?
C37 C38 C39 C40 92.1(4) . . . . ?
C34 C38 C39 C40 -82.4(3) . . . . ?
C38 C39 C40 N41 -64.4(3) . . . . ?
N36 C35 C42 C43 178.1(4) . . . . ?
C34 C35 C42 C43 -1.3(5) . . . . ?
C35 C42 C43 C32 -0.1(6) . . . . ?
O31 C32 C43 C42 -178.0(3) . . . . ?
C33 C32 C43 C42 1.3(5) . . . . ?
C32 O31 C44 C45 -177.9(3) . . . . ?
O31 C44 C45 C50 103.3(3) . . . . ?
O31 C44 C45 C46 -78.6(3) . . . . ?
C50 C45 C46 C47 -1.8(4) . . . . ?
C44 C45 C46 C47 -179.9(3) . . . . ?
C45 C46 C47 C48 0.5(5) . . . . ?
C46 C47 C48 C49 1.3(5) . . . . ?
C47 C48 C49 C50 -1.9(5) . . . . ?
C46 C45 C50 C49 1.2(5) . . . . ?
C44 C45 C50 C49 179.3(3) . . . . ?
C48 C49 C50 C45 0.6(5) . . . . ?
C7 C8 C90 C100 -106.6(5) . . . . ?
C4 C8 C90 C100 73.2(5) . . . . ?
C8 C90 C100 N110 58.1(5) . . . . ?
C7 C8 C91 C101 -100.7(9) . . . . ?
C4 C8 C91 C101 48.2(11) . . . . ?
C8 C91 C101 N111 59.1(12) . . . . ?

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_I_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 1585753'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   19.8981(7)
_cell_length_b                   8.0213(2)
_cell_length_c                   10.8806(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.435(3)
_cell_angle_gamma                90
_cell_volume                     1707.92(9)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-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'
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'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 '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'
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'


_cell_formula_units_Z            4

# Given Formula = C18 H15 N3 O1 S1 
# Dc =      1.25 Fooo =    672.00 Mu =     17.38 M =    321.40
# Found Formula = C18 H19.00 N3 O1 S1 
# Dc =      1.27 FOOO =    688.00 Mu =     17.39 M =    325.43

_chemical_formula_sum            'C18 H19 N3 O S'
_chemical_formula_moiety         'C17 H19 N2 O, C N S'
_chemical_compound_source        ?
_chemical_formula_weight         325.43


_cell_measurement_reflns_used    4441
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    160

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.019
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_max          0.119

_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             687.997
_exptl_absorpt_coefficient_mu    1.739

# 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  0.83
_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     1.54184
_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      160
_diffrn_reflns_number            10335
_reflns_number_total             3450
_diffrn_reflns_av_R_equivalents  0.022
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3450 
# Theoretical number of reflections is about 6975 


_diffrn_reflns_theta_min         4.519
_diffrn_reflns_theta_max         74.390
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        74.390
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -24
_reflns_limit_h_max              24
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.44
_oxford_diffrn_Wilson_scale      0.02

_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         0.38


# 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         3450
_refine_ls_number_restraints     0
_refine_ls_number_parameters     208
_oxford_refine_ls_R_factor_ref   0.0401
_refine_ls_wR_factor_ref         0.0873
_refine_ls_goodness_of_fit_ref   0.9770
_refine_ls_shift/su_max          0.0014643
_refine_ls_shift/su_mean         0.0001047


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3450
_refine_ls_R_factor_all          0.0401
_refine_ls_wR_factor_all         0.0873

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2987
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_gt          0.0819

# 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 .


_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 + 0.91P] 
 ,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 0.62039(6) 0.43432(16) 0.19864(11) 0.0265 1.0000 Uani . . . . . .
C2 C 0.68822(7) 0.36145(18) 0.25112(13) 0.0241 1.0000 Uani . . . . . .
C3 C 0.68470(8) 0.27330(18) 0.37358(13) 0.0260 1.0000 Uani . . . . . .
C4 C 0.66947(7) 0.38805(18) 0.47353(12) 0.0244 1.0000 Uani . . . . . .
C5 C 0.60878(8) 0.40622(19) 0.51469(13) 0.0274 1.0000 Uani . . . . . .
N6 N 0.61647(6) 0.51410(17) 0.61385(11) 0.0283 1.0000 Uani . . . . . .
C7 C 0.68291(7) 0.57143(18) 0.63770(13) 0.0251 1.0000 Uani . . . . . .
C8 C 0.71757(7) 0.49566(17) 0.55045(12) 0.0232 1.0000 Uani . . . . . .
C9 C 0.71644(8) 0.67657(19) 0.73116(14) 0.0298 1.0000 Uani . . . . . .
C10 C 0.78466(8) 0.7091(2) 0.73260(15) 0.0317 1.0000 Uani . . . . . .
C11 C 0.81974(8) 0.63731(19) 0.64397(14) 0.0292 1.0000 Uani . . . . . .
C12 C 0.78730(7) 0.52943(18) 0.55349(13) 0.0263 1.0000 Uani . . . . . .
O13 O 0.88762(6) 0.68157(15) 0.65882(11) 0.0370 1.0000 Uani . . . . . .
C14 C 0.92743(8) 0.5954(2) 0.58149(16) 0.0369 1.0000 Uani . . . . . .
C15 C 0.99973(8) 0.6543(2) 0.61784(14) 0.0301 1.0000 Uani . . . . . .
C16 C 1.02352(8) 0.7859(2) 0.55484(16) 0.0354 1.0000 Uani . . . . . .
C17 C 1.08952(9) 0.8453(2) 0.59147(19) 0.0439 1.0000 Uani . . . . . .
C18 C 1.13234(9) 0.7724(3) 0.69054(18) 0.0469 1.0000 Uani . . . . . .
C19 C 1.11001(10) 0.6384(3) 0.75111(17) 0.0531 1.0000 Uani . . . . . .
C20 C 1.04394(10) 0.5794(3) 0.71557(16) 0.0431 1.0000 Uani . . . . . .
N21 N 0.59629(9) 0.5753(2) 0.96073(14) 0.0491 1.0000 Uani . . . . . .
C22 C 0.56405(8) 0.6599(2) 0.88644(14) 0.0295 1.0000 Uani . . . . . .
S23 S 0.519476(19) 0.77750(5) 0.77677(4) 0.0306 1.0000 Uani . . . . . .
H121 H 0.8110 0.4775 0.4960 0.0317 1.0000 Uiso R . . . . .
H51 H 0.5660 0.3540 0.4829 0.0331 1.0000 Uiso R . . . . .
H31 H 0.7292 0.2213 0.4018 0.0312 1.0000 Uiso R . . . . .
H32 H 0.6507 0.1853 0.3574 0.0313 1.0000 Uiso R . . . . .
H21 H 0.7214 0.4520 0.2632 0.0287 1.0000 Uiso R . . . . .
H22 H 0.7000 0.2822 0.1905 0.0278 1.0000 Uiso R . . . . .
H91 H 0.6941 0.7208 0.7932 0.0355 1.0000 Uiso R . . . . .
H101 H 0.8085 0.7791 0.7939 0.0378 1.0000 Uiso R . . . . .
H141 H 0.9248 0.4763 0.5959 0.0435 1.0000 Uiso R . . . . .
H142 H 0.9098 0.6207 0.4944 0.0440 1.0000 Uiso R . . . . .
H161 H 0.9943 0.8340 0.4868 0.0435 1.0000 Uiso R . . . . .
H171 H 1.1047 0.9371 0.5469 0.0533 1.0000 Uiso R . . . . .
H181 H 1.1773 0.8141 0.7173 0.0568 1.0000 Uiso R . . . . .
H191 H 1.1393 0.5898 0.8188 0.0643 1.0000 Uiso R . . . . .
H201 H 1.0285 0.4887 0.7562 0.0526 1.0000 Uiso R . . . . .
H12 H 0.6198 0.4818 0.1216 0.0409 1.0000 Uiso R . . . . .
H13 H 0.6088 0.5153 0.2505 0.0397 1.0000 Uiso R . . . . .
H61 H 0.5841 0.5538 0.6467 0.0352 1.0000 Uiso R . . . . .
H11 H 0.5871 0.3551 0.1922 0.0405 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.62(13)
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 . 1.4867(18) yes
N1 . H12 . 0.919 no
N1 . H13 . 0.917 no
N1 . H11 . 0.912 no
C2 . C3 . 1.5212(19) yes
C2 . H21 . 0.975 no
C2 . H22 . 0.975 no
C3 . C4 . 1.497(2) yes
C3 . H31 . 0.977 no
C3 . H32 . 0.972 no
C4 . C5 . 1.370(2) yes
C4 . C8 . 1.4392(19) yes
C5 . N6 . 1.3699(19) yes
C5 . H51 . 0.956 no
N6 . C7 . 1.3791(19) yes
N6 . H61 . 0.854 no
C7 . C8 . 1.4084(19) yes
C7 . C9 . 1.395(2) yes
C8 . C12 . 1.408(2) yes
C9 . C10 . 1.380(2) yes
C9 . H91 . 0.942 no
C10 . C11 . 1.412(2) yes
C10 . H101 . 0.933 no
C11 . C12 . 1.380(2) yes
C11 . O13 . 1.3775(18) yes
C12 . H121 . 0.945 no
O13 . C14 . 1.4334(18) yes
C14 . C15 . 1.498(2) yes
C14 . H141 . 0.971 no
C14 . H142 . 0.970 no
C15 . C16 . 1.388(2) yes
C15 . C20 . 1.388(2) yes
C16 . C17 . 1.386(2) yes
C16 . H161 . 0.938 no
C17 . C18 . 1.378(3) yes
C17 . H171 . 0.959 no
C18 . C19 . 1.376(3) yes
C18 . H181 . 0.949 no
C19 . C20 . 1.385(3) yes
C19 . H191 . 0.937 no
C20 . H201 . 0.931 no
N21 . C22 . 1.157(2) yes
C22 . S23 . 1.6481(16) 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 . H12 . 112.0 no
C2 . N1 . H13 . 110.7 no
H12 . N1 . H13 . 107.7 no
C2 . N1 . H11 . 110.6 no
H12 . N1 . H11 . 109.3 no
H13 . N1 . H11 . 106.3 no
N1 . C2 . C3 . 109.67(11) yes
N1 . C2 . H21 . 107.8 no
C3 . C2 . H21 . 111.5 no
N1 . C2 . H22 . 108.0 no
C3 . C2 . H22 . 110.1 no
H21 . C2 . H22 . 109.7 no
C2 . C3 . C4 . 113.45(12) yes
C2 . C3 . H31 . 106.9 no
C4 . C3 . H31 . 109.0 no
C2 . C3 . H32 . 108.7 no
C4 . C3 . H32 . 110.6 no
H31 . C3 . H32 . 108.0 no
C3 . C4 . C5 . 127.54(13) yes
C3 . C4 . C8 . 126.19(13) yes
C5 . C4 . C8 . 106.19(13) yes
C4 . C5 . N6 . 110.20(13) yes
C4 . C5 . H51 . 128.0 no
N6 . C5 . H51 . 121.8 no
C5 . N6 . C7 . 108.99(12) yes
C5 . N6 . H61 . 125.5 no
C7 . N6 . H61 . 124.6 no
N6 . C7 . C8 . 107.40(12) yes
N6 . C7 . C9 . 130.88(13) yes
C8 . C7 . C9 . 121.63(13) yes
C4 . C8 . C7 . 107.19(12) yes
C4 . C8 . C12 . 132.66(13) yes
C7 . C8 . C12 . 120.12(13) yes
C7 . C9 . C10 . 117.55(14) yes
C7 . C9 . H91 . 121.6 no
C10 . C9 . H91 . 120.8 no
C9 . C10 . C11 . 121.50(14) yes
C9 . C10 . H101 . 119.5 no
C11 . C10 . H101 . 119.0 no
C10 . C11 . C12 . 121.19(14) yes
C10 . C11 . O13 . 114.23(13) yes
C12 . C11 . O13 . 124.56(13) yes
C8 . C12 . C11 . 117.97(13) yes
C8 . C12 . H121 . 120.4 no
C11 . C12 . H121 . 121.6 no
C11 . O13 . C14 . 116.18(12) yes
O13 . C14 . C15 . 107.42(12) yes
O13 . C14 . H141 . 109.1 no
C15 . C14 . H141 . 110.2 no
O13 . C14 . H142 . 109.4 no
C15 . C14 . H142 . 110.6 no
H141 . C14 . H142 . 110.1 no
C14 . C15 . C16 . 120.45(15) yes
C14 . C15 . C20 . 120.71(16) yes
C16 . C15 . C20 . 118.84(15) yes
C15 . C16 . C17 . 120.64(16) yes
C15 . C16 . H161 . 119.0 no
C17 . C16 . H161 . 120.3 no
C16 . C17 . C18 . 119.91(18) yes
C16 . C17 . H171 . 119.1 no
C18 . C17 . H171 . 121.0 no
C17 . C18 . C19 . 119.92(17) yes
C17 . C18 . H181 . 120.3 no
C19 . C18 . H181 . 119.7 no
C18 . C19 . C20 . 120.40(18) yes
C18 . C19 . H191 . 119.5 no
C20 . C19 . H191 . 120.0 no
C15 . C20 . C19 . 120.23(18) yes
C15 . C20 . H201 . 119.0 no
C19 . C20 . H201 . 120.8 no
N21 . C22 . S23 . 177.96(15) 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
N1 . H12 . N21 1_554 167 0.92 1.88 2.786(2) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_I_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 1585750'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   19.6674(3)
_cell_length_b                   8.12240(10)
_cell_length_c                   10.8447(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.2892(16)
_cell_angle_gamma                90
_cell_volume                     1671.09(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-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'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 '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'


_cell_formula_units_Z            4

# Given Formula = C17 H19 I1 N2 O1 
# Dc =      1.57 Fooo =    784.00 Mu =    150.54 M =    394.26
# Found Formula = C17 H19 I1 N2 O1 
# Dc =      1.57 FOOO =    784.00 Mu =    150.54 M =    394.26

_chemical_formula_sum            'C17 H19 I N2 O'
_chemical_formula_moiety         'C17 H19 N2 O, I'
_chemical_compound_source        ?
_chemical_formula_weight         394.26


_cell_measurement_reflns_used    19152
_cell_measurement_theta_min      5
_cell_measurement_theta_max      79
_cell_measurement_temperature    160

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.021
_exptl_crystal_size_mid          0.438
_exptl_crystal_size_max          0.563

_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    15.054

# Sheldrick geometric approximatio 0.00 0.73 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.02
_exptl_absorpt_correction_T_max  0.73
_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      160
_diffrn_reflns_number            33730
_reflns_number_total             3418
_diffrn_reflns_av_R_equivalents  0.053
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3418 
# Theoretical number of reflections is about 6832 


_diffrn_reflns_theta_min         4.662
_diffrn_reflns_theta_max         74.462
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        74.462
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -24
_reflns_limit_h_max              23
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.20
_oxford_diffrn_Wilson_scale      0.07

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

_refine_diff_density_min         -0.50
_refine_diff_density_max         1.01


# 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         3418
_refine_ls_number_restraints     0
_refine_ls_number_parameters     190
_oxford_refine_ls_R_factor_ref   0.0246
_refine_ls_wR_factor_ref         0.0622
_refine_ls_goodness_of_fit_ref   0.9797
_refine_ls_shift/su_max          0.0007045
_refine_ls_shift/su_mean         0.0000236


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3418
_refine_ls_R_factor_all          0.0246
_refine_ls_wR_factor_all         0.0622

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3145
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_gt          0.0605

# 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 .


_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 + 1.89P] 
 ,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 0.10996(11) 0.5194(3) 0.4129(2) 0.0313 1.0000 Uani . . . . . .
C2 C 0.17260(12) 0.4089(3) 0.4347(2) 0.0277 1.0000 Uani . . . . . .
C3 C 0.16597(14) 0.2981(3) 0.3187(2) 0.0288 1.0000 Uani . . . . . .
C4 C 0.16082(12) 0.3910(3) 0.1978(2) 0.0243 1.0000 Uani . . . . . .
C5 C 0.10342(13) 0.3991(3) 0.0937(2) 0.0269 1.0000 Uani . . . . . .
N6 N 0.11888(10) 0.4932(2) -0.00011(18) 0.0267 1.0000 Uani . . . . . .
C7 C 0.18683(12) 0.5506(3) 0.0427(2) 0.0246 1.0000 Uani . . . . . .
C8 C 0.21481(12) 0.4892(3) 0.1676(2) 0.0236 1.0000 Uani . . . . . .
C9 C 0.22725(13) 0.6480(3) -0.0176(2) 0.0284 1.0000 Uani . . . . . .
C10 C 0.29505(14) 0.6856(3) 0.0502(3) 0.0312 1.0000 Uani . . . . . .
C11 C 0.32385(13) 0.6256(3) 0.1758(2) 0.0280 1.0000 Uani . . . . . .
C12 C 0.28482(12) 0.5271(3) 0.2349(2) 0.0259 1.0000 Uani . . . . . .
O13 O 0.39290(10) 0.6714(2) 0.2291(2) 0.0361 1.0000 Uani . . . . . .
C14 C 0.42955(13) 0.5835(3) 0.3419(3) 0.0335 1.0000 Uani . . . . . .
C15 C 0.50441(13) 0.6431(3) 0.3787(3) 0.0287 1.0000 Uani . . . . . .
C16 C 0.52404(15) 0.7737(3) 0.4641(3) 0.0348 1.0000 Uani . . . . . .
C17 C 0.59268(16) 0.8307(3) 0.4965(3) 0.0406 1.0000 Uani . . . . . .
C18 C 0.64257(14) 0.7583(4) 0.4460(3) 0.0402 1.0000 Uani . . . . . .
C19 C 0.62385(15) 0.6264(4) 0.3632(3) 0.0435 1.0000 Uani . . . . . .
C20 C 0.55488(15) 0.5692(4) 0.3296(3) 0.0370 1.0000 Uani . . . . . .
I21 I 0.057254(8) 0.836126(19) 0.180144(13) 0.0291 1.0000 Uani . . . . . .
H21 H 0.2145 0.4767 0.4488 0.0331 1.0000 Uiso R . . . . .
H22 H 0.1755 0.3442 0.5103 0.0331 1.0000 Uiso R . . . . .
H31 H 0.2069 0.2268 0.3355 0.0347 1.0000 Uiso R . . . . .
H32 H 0.1250 0.2302 0.3088 0.0341 1.0000 Uiso R . . . . .
H51 H 0.0593 0.3484 0.0834 0.0322 1.0000 Uiso R . . . . .
H91 H 0.2096 0.6847 -0.1020 0.0339 1.0000 Uiso R . . . . .
H101 H 0.3230 0.7511 0.0140 0.0372 1.0000 Uiso R . . . . .
H121 H 0.3042 0.4854 0.3170 0.0311 1.0000 Uiso R . . . . .
H141 H 0.4078 0.6044 0.4103 0.0409 1.0000 Uiso R . . . . .
H142 H 0.4274 0.4673 0.3223 0.0397 1.0000 Uiso R . . . . .
H161 H 0.4903 0.8233 0.4999 0.0424 1.0000 Uiso R . . . . .
H171 H 0.6061 0.9188 0.5542 0.0483 1.0000 Uiso R . . . . .
H181 H 0.6886 0.7971 0.4662 0.0476 1.0000 Uiso R . . . . .
H191 H 0.6573 0.5741 0.3301 0.0526 1.0000 Uiso R . . . . .
H201 H 0.5428 0.4801 0.2749 0.0443 1.0000 Uiso R . . . . .
H12 H 0.1082 0.5866 0.3471 0.0468 1.0000 Uiso R . . . . .
H13 H 0.1108 0.5788 0.4826 0.0466 1.0000 Uiso R . . . . .
H61 H 0.0906 0.5156 -0.0712 0.0323 1.0000 Uiso R . . . . .
H11 H 0.0712 0.4592 0.3954 0.0473 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.90(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 . 1.492(3) yes
N1 . H12 . 0.891 no
N1 . H13 . 0.892 no
N1 . H11 . 0.883 no
C2 . C3 . 1.524(3) yes
C2 . H21 . 0.969 no
C2 . H22 . 0.963 no
C3 . C4 . 1.493(3) yes
C3 . H31 . 0.970 no
C3 . H32 . 0.958 no
C4 . C5 . 1.371(3) yes
C4 . C8 . 1.433(3) yes
C5 . N6 . 1.369(3) yes
C5 . H51 . 0.939 no
N6 . C7 . 1.376(3) yes
N6 . H61 . 0.843 no
C7 . C8 . 1.412(3) yes
C7 . C9 . 1.400(3) yes
C8 . C12 . 1.412(3) yes
C9 . C10 . 1.376(4) yes
C9 . H91 . 0.938 no
C10 . C11 . 1.417(4) yes
C10 . H101 . 0.924 no
C11 . C12 . 1.378(3) yes
C11 . O13 . 1.379(3) yes
C12 . H121 . 0.934 no
O13 . C14 . 1.435(3) yes
C14 . C15 . 1.500(3) yes
C14 . H141 . 0.965 no
C14 . H142 . 0.966 no
C15 . C16 . 1.394(4) yes
C15 . C20 . 1.381(4) yes
C16 . C17 . 1.382(4) yes
C16 . H161 . 0.943 no
C17 . C18 . 1.376(5) yes
C17 . H171 . 0.941 no
C18 . C19 . 1.384(5) yes
C18 . H181 . 0.928 no
C19 . C20 . 1.388(4) yes
C19 . H191 . 0.931 no
C20 . H201 . 0.926 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 . H12 . 110.5 no
C2 . N1 . H13 . 111.1 no
H12 . N1 . H13 . 109.6 no
C2 . N1 . H11 . 109.3 no
H12 . N1 . H11 . 108.5 no
H13 . N1 . H11 . 107.7 no
N1 . C2 . C3 . 109.72(19) yes
N1 . C2 . H21 . 108.4 no
C3 . C2 . H21 . 110.5 no
N1 . C2 . H22 . 108.9 no
C3 . C2 . H22 . 110.7 no
H21 . C2 . H22 . 108.6 no
C2 . C3 . C4 . 113.4(2) yes
C2 . C3 . H31 . 108.1 no
C4 . C3 . H31 . 109.1 no
C2 . C3 . H32 . 108.6 no
C4 . C3 . H32 . 109.4 no
H31 . C3 . H32 . 108.0 no
C3 . C4 . C5 . 126.7(2) yes
C3 . C4 . C8 . 126.8(2) yes
C5 . C4 . C8 . 106.5(2) yes
C4 . C5 . N6 . 110.0(2) yes
C4 . C5 . H51 . 127.7 no
N6 . C5 . H51 . 122.3 no
C5 . N6 . C7 . 108.96(19) yes
C5 . N6 . H61 . 125.3 no
C7 . N6 . H61 . 125.7 no
N6 . C7 . C8 . 107.6(2) yes
N6 . C7 . C9 . 130.9(2) yes
C8 . C7 . C9 . 121.5(2) yes
C4 . C8 . C7 . 106.9(2) yes
C4 . C8 . C12 . 133.1(2) yes
C7 . C8 . C12 . 119.9(2) yes
C7 . C9 . C10 . 117.7(2) yes
C7 . C9 . H91 . 121.7 no
C10 . C9 . H91 . 120.6 no
C9 . C10 . C11 . 121.5(2) yes
C9 . C10 . H101 . 120.1 no
C11 . C10 . H101 . 118.4 no
C10 . C11 . C12 . 121.1(2) yes
C10 . C11 . O13 . 114.2(2) yes
C12 . C11 . O13 . 124.7(2) yes
C8 . C12 . C11 . 118.2(2) yes
C8 . C12 . H121 . 120.7 no
C11 . C12 . H121 . 121.0 no
C11 . O13 . C14 . 116.15(19) yes
O13 . C14 . C15 . 107.7(2) yes
O13 . C14 . H141 . 110.1 no
C15 . C14 . H141 . 110.0 no
O13 . C14 . H142 . 108.4 no
C15 . C14 . H142 . 110.9 no
H141 . C14 . H142 . 109.7 no
C14 . C15 . C16 . 120.2(3) yes
C14 . C15 . C20 . 120.8(2) yes
C16 . C15 . C20 . 119.0(2) yes
C15 . C16 . C17 . 120.3(3) yes
C15 . C16 . H161 . 119.8 no
C17 . C16 . H161 . 119.9 no
C16 . C17 . C18 . 120.5(3) yes
C16 . C17 . H171 . 120.5 no
C18 . C17 . H171 . 119.0 no
C17 . C18 . C19 . 119.6(3) yes
C17 . C18 . H181 . 120.9 no
C19 . C18 . H181 . 119.5 no
C18 . C19 . C20 . 120.2(3) yes
C18 . C19 . H191 . 120.6 no
C20 . C19 . H191 . 119.2 no
C19 . C20 . C15 . 120.4(3) yes
C19 . C20 . H201 . 119.8 no
C15 . C20 . H201 . 119.8 no


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_mbbsp_171024_ephi_mo
_database_code_depnum_ccdc_archive 'CCDC 1585758'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 I N O'
_chemical_formula_weight         293.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   7.32726(12)
_cell_length_b                   18.9411(3)
_cell_length_c                   25.6662(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3562.12(11)
_cell_formula_units_Z            12
_cell_measurement_temperature    160.0(1)
_cell_measurement_reflns_used    39069
_cell_measurement_theta_min      2.281
_cell_measurement_theta_max      33.430

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.664
_shelx_estimated_absorpt_T_min   0.512
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.419
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27e (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            88148
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         33.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12569
_reflns_number_gt                11728
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     0.875
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Rigaku, 2015)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku, 2015)'
_computing_data_reduction        'CrysAlis PRO (Rigaku, 2015)'
_computing_structure_solution    'Superflip (Palatinus, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²+1.0054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(5)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         12569
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0480
_refine_ls_wR_factor_gt          0.0472
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3448(3) 0.22780(13) 0.84456(10) 0.0192(4) Uani 1 1 d . . . . .
H1A H 0.2627 0.2655 0.8306 0.023 Uiso 1 1 calc R U . . .
C2 C 0.5367(4) 0.26081(13) 0.84834(9) 0.0208(5) Uani 1 1 d . . . . .
H2A H 0.5278 0.3059 0.8684 0.025 Uiso 1 1 calc R U . . .
C3 C 0.6811(4) 0.21418(16) 0.87381(11) 0.0285(6) Uani 1 1 d . . . . .
H3A H 0.6826 0.1679 0.8567 0.043 Uiso 1 1 calc R U . . .
H3B H 0.6522 0.2082 0.9108 0.043 Uiso 1 1 calc R U . . .
H3C H 0.8011 0.2365 0.8703 0.043 Uiso 1 1 calc R U . . .
C4 C 0.4854(5) 0.31992(15) 0.76006(11) 0.0328(6) Uani 1 1 d . . . . .
H4A H 0.3804 0.2915 0.7491 0.049 Uiso 1 1 calc R U . . .
H4B H 0.5544 0.3349 0.7293 0.049 Uiso 1 1 calc R U . . .
H4C H 0.4426 0.3616 0.7791 0.049 Uiso 1 1 calc R U . . .
C5 C 0.2711(3) 0.20842(13) 0.89788(10) 0.0213(5) Uani 1 1 d . . . . .
C6 C 0.3042(4) 0.14273(14) 0.92066(11) 0.0259(5) Uani 1 1 d . . . . .
H6A H 0.3739 0.1084 0.9024 0.031 Uiso 1 1 calc R U . . .
C7 C 0.2361(5) 0.12709(16) 0.96989(11) 0.0323(6) Uani 1 1 d . . . . .
H7A H 0.2596 0.0823 0.9851 0.039 Uiso 1 1 calc R U . . .
C8 C 0.1337(5) 0.17691(18) 0.99677(12) 0.0361(7) Uani 1 1 d . . . . .
H8A H 0.0872 0.1663 1.0304 0.043 Uiso 1 1 calc R U . . .
C9 C 0.0996(4) 0.24214(19) 0.97427(12) 0.0351(7) Uani 1 1 d . . . . .
H9A H 0.0297 0.2763 0.9926 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1671(4) 0.25769(16) 0.92512(12) 0.0280(6) Uani 1 1 d . . . . .
H10A H 0.1423 0.3024 0.9099 0.034 Uiso 1 1 calc R U . . .
C11 C 0.3429(3) 0.50344(13) 0.88232(9) 0.0193(4) Uani 1 1 d . . . . .
H11A H 0.2563 0.5249 0.8567 0.023 Uiso 1 1 calc R U . . .
C12 C 0.5226(4) 0.54484(13) 0.88054(9) 0.0209(5) Uani 1 1 d . . . . .
H12A H 0.4972 0.5942 0.8923 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6700(4) 0.51440(17) 0.91537(12) 0.0312(6) Uani 1 1 d . . . . .
H13A H 0.6994 0.4664 0.9039 0.047 Uiso 1 1 calc R U . . .
H13B H 0.6264 0.5132 0.9515 0.047 Uiso 1 1 calc R U . . .
H13C H 0.7796 0.5439 0.9132 0.047 Uiso 1 1 calc R U . . .
C14 C 0.7373(4) 0.59798(16) 0.81466(11) 0.0317(6) Uani 1 1 d . . . . .
H14A H 0.7068 0.6443 0.8292 0.048 Uiso 1 1 calc R U . . .
H14B H 0.7567 0.6024 0.7770 0.048 Uiso 1 1 calc R U . . .
H14C H 0.8489 0.5802 0.8311 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2585(3) 0.50782(14) 0.93608(10) 0.0206(5) Uani 1 1 d . . . . .
C16 C 0.2539(4) 0.45036(17) 0.96953(12) 0.0321(6) Uani 1 1 d . . . . .
H16A H 0.3019 0.4063 0.9584 0.039 Uiso 1 1 calc R U . . .
C17 C 0.1798(5) 0.4567(2) 1.01907(14) 0.0470(9) Uani 1 1 d . . . . .
H17A H 0.1769 0.4170 1.0416 0.056 Uiso 1 1 calc R U . . .
C18 C 0.1103(5) 0.5204(3) 1.03574(13) 0.0480(10) Uani 1 1 d . . . . .
H18A H 0.0589 0.5246 1.0696 0.058 Uiso 1 1 calc R U . . .
C19 C 0.1159(5) 0.5779(2) 1.00309(13) 0.0437(9) Uani 1 1 d . . . . .
H19A H 0.0701 0.6221 1.0147 0.052 Uiso 1 1 calc R U . . .
C20 C 0.1883(4) 0.57177(16) 0.95304(11) 0.0312(6) Uani 1 1 d . . . . .
H20A H 0.1894 0.6115 0.9305 0.037 Uiso 1 1 calc R U . . .
C21 C 0.9499(4) 0.84408(14) 0.85131(10) 0.0239(5) Uani 1 1 d . . . . .
H21A H 0.9017 0.8429 0.8149 0.029 Uiso 1 1 calc R U . . .
C22 C 0.9515(4) 0.92112(13) 0.86978(10) 0.0222(5) Uani 1 1 d . . . . .
H22A H 0.8225 0.9366 0.8755 0.027 Uiso 1 1 calc R U . . .
C23 C 1.0576(4) 0.93199(16) 0.92027(11) 0.0312(6) Uani 1 1 d . . . . .
H23A H 1.1868 0.9212 0.9144 0.047 Uiso 1 1 calc R U . . .
H23B H 1.0090 0.9006 0.9473 0.047 Uiso 1 1 calc R U . . .
H23C H 1.0452 0.9812 0.9316 0.047 Uiso 1 1 calc R U . . .
C24 C 1.0035(4) 1.04336(15) 0.83262(15) 0.0380(7) Uani 1 1 d . . . . .
H24A H 0.8723 1.0531 0.8340 0.057 Uiso 1 1 calc R U . . .
H24B H 1.0573 1.0680 0.8028 0.057 Uiso 1 1 calc R U . . .
H24C H 1.0615 1.0599 0.8648 0.057 Uiso 1 1 calc R U . . .
C25 C 0.8262(4) 0.79895(13) 0.88534(10) 0.0222(5) Uani 1 1 d . . . . .
C26 C 0.8945(4) 0.75051(16) 0.92085(13) 0.0318(6) Uani 1 1 d . . . . .
H26A H 1.0226 0.7443 0.9243 0.038 Uiso 1 1 calc R U . . .
C27 C 0.7758(5) 0.71089(16) 0.95149(13) 0.0370(7) Uani 1 1 d . . . . .
H27A H 0.8236 0.6781 0.9759 0.044 Uiso 1 1 calc R U . . .
C28 C 0.5889(5) 0.71886(16) 0.94671(12) 0.0321(6) Uani 1 1 d . . . . .
H28A H 0.5086 0.6914 0.9676 0.039 Uiso 1 1 calc R U . . .
C29 C 0.5200(4) 0.76701(15) 0.91141(11) 0.0292(6) Uani 1 1 d . . . . .
H29A H 0.3918 0.7728 0.9080 0.035 Uiso 1 1 calc R U . . .
C30 C 0.6373(4) 0.80684(14) 0.88090(11) 0.0242(5) Uani 1 1 d . . . . .
H30A H 0.5887 0.8398 0.8567 0.029 Uiso 1 1 calc R U . . .
N1 N 0.6046(3) 0.27723(12) 0.79432(9) 0.0240(4) Uani 1 1 d . . . . .
H1C H 0.7132 0.3002 0.7974 0.029 Uiso 1 1 calc R U . . .
H1B H 0.6273 0.2355 0.7779 0.029 Uiso 1 1 calc R U . . .
N11 N 0.5843(3) 0.54773(14) 0.82473(9) 0.0271(5) Uani 1 1 d . . . . .
H11C H 0.6199 0.5037 0.8148 0.033 Uiso 1 1 calc R U . . .
H11B H 0.4876 0.5602 0.8045 0.033 Uiso 1 1 calc R U . . .
N21 N 1.0333(4) 0.96580(12) 0.82694(9) 0.0282(5) Uani 1 1 d . . . . .
H21C H 1.1556 0.9575 0.8258 0.034 Uiso 1 1 calc R U . . .
H21B H 0.9852 0.9517 0.7959 0.034 Uiso 1 1 calc R U . . .
O1 O 0.3429(3) 0.17219(9) 0.80727(7) 0.0244(4) Uani 1 1 d . . . . .
H1 H 0.4018 0.1376 0.8189 0.037 Uiso 1 1 calc R U . . .
O11 O 0.3816(3) 0.43282(10) 0.86628(8) 0.0273(4) Uani 1 1 d . . . . .
H11 H 0.2926 0.4168 0.8494 0.041 Uiso 1 1 calc R U . . .
O21 O 1.1340(3) 0.82223(11) 0.85029(10) 0.0359(5) Uani 1 1 d . . . . .
H21 H 1.1427 0.7843 0.8335 0.054 Uiso 1 1 calc R U . . .
I1 I 0.96150(2) 0.40083(2) 0.80605(2) 0.02854(4) Uani 1 1 d . . . . .
I11 I 0.20776(3) 0.65950(2) 0.79216(2) 0.02858(4) Uani 1 1 d . . . . .
I21 I 0.50045(2) 0.99760(2) 0.80887(2) 0.02270(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.423(3) . ?
C1 C5 1.516(4) . ?
C1 C2 1.542(4) . ?
C1 H1A 1.0000 . ?
C2 N1 1.506(3) . ?
C2 C3 1.525(4) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N1 1.480(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.393(4) . ?
C5 C6 1.396(4) . ?
C6 C7 1.391(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.389(5) . ?
C7 H7A 0.9500 . ?
C8 C9 1.387(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.387(4) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 O11 1.428(3) . ?
C11 C15 1.514(3) . ?
C11 C12 1.533(3) . ?
C11 H11A 1.0000 . ?
C12 N11 1.503(3) . ?
C12 C13 1.516(4) . ?
C12 H12A 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N11 1.493(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.386(4) . ?
C15 C16 1.387(4) . ?
C16 C17 1.388(5) . ?
C16 H16A 0.9500 . ?
C17 C18 1.377(6) . ?
C17 H17A 0.9500 . ?
C18 C19 1.374(6) . ?
C18 H18A 0.9500 . ?
C19 C20 1.395(4) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C21 O21 1.411(3) . ?
C21 C25 1.522(4) . ?
C21 C22 1.534(4) . ?
C21 H21A 1.0000 . ?
C22 N21 1.512(3) . ?
C22 C23 1.525(4) . ?
C22 H22A 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 N21 1.492(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.387(4) . ?
C25 C30 1.397(4) . ?
C26 C27 1.392(5) . ?
C26 H26A 0.9500 . ?
C27 C28 1.383(5) . ?
C27 H27A 0.9500 . ?
C28 C29 1.381(4) . ?
C28 H28A 0.9500 . ?
C29 C30 1.386(4) . ?
C29 H29A 0.9500 . ?
C30 H30A 0.9500 . ?
N1 H1C 0.9100 . ?
N1 H1B 0.9100 . ?
N11 H11C 0.9100 . ?
N11 H11B 0.9100 . ?
N21 H21C 0.9100 . ?
N21 H21B 0.9100 . ?
O1 H1 0.8400 . ?
O11 H11 0.8400 . ?
O21 H21 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C5 115.1(2) . . ?
O1 C1 C2 110.6(2) . . ?
C5 C1 C2 111.5(2) . . ?
O1 C1 H1A 106.4 . . ?
C5 C1 H1A 106.4 . . ?
C2 C1 H1A 106.4 . . ?
N1 C2 C3 106.6(2) . . ?
N1 C2 C1 109.1(2) . . ?
C3 C2 C1 115.1(2) . . ?
N1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 118.8(3) . . ?
C10 C5 C1 119.1(2) . . ?
C6 C5 C1 122.1(2) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C9 C10 C5 120.6(3) . . ?
C9 C10 H10A 119.7 . . ?
C5 C10 H10A 119.7 . . ?
O11 C11 C15 113.3(2) . . ?
O11 C11 C12 107.47(19) . . ?
C15 C11 C12 110.5(2) . . ?
O11 C11 H11A 108.5 . . ?
C15 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
N11 C12 C13 111.2(2) . . ?
N11 C12 C11 107.8(2) . . ?
C13 C12 C11 113.6(2) . . ?
N11 C12 H12A 108.0 . . ?
C13 C12 H12A 108.0 . . ?
C11 C12 H12A 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N11 C14 H14A 109.5 . . ?
N11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.8(3) . . ?
C20 C15 C11 119.1(2) . . ?
C16 C15 C11 122.1(2) . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C15 C20 C19 120.2(3) . . ?
C15 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
O21 C21 C25 114.5(2) . . ?
O21 C21 C22 106.1(2) . . ?
C25 C21 C22 111.2(2) . . ?
O21 C21 H21A 108.3 . . ?
C25 C21 H21A 108.3 . . ?
C22 C21 H21A 108.3 . . ?
N21 C22 C23 109.9(2) . . ?
N21 C22 C21 108.1(2) . . ?
C23 C22 C21 113.2(2) . . ?
N21 C22 H22A 108.5 . . ?
C23 C22 H22A 108.5 . . ?
C21 C22 H22A 108.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N21 C24 H24A 109.5 . . ?
N21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 118.8(3) . . ?
C26 C25 C21 122.3(3) . . ?
C30 C25 C21 118.9(2) . . ?
C25 C26 C27 120.2(3) . . ?
C25 C26 H26A 119.9 . . ?
C27 C26 H26A 119.9 . . ?
C28 C27 C26 120.6(3) . . ?
C28 C27 H27A 119.7 . . ?
C26 C27 H27A 119.7 . . ?
C29 C28 C27 119.5(3) . . ?
C29 C28 H28A 120.3 . . ?
C27 C28 H28A 120.3 . . ?
C28 C29 C30 120.2(3) . . ?
C28 C29 H29A 119.9 . . ?
C30 C29 H29A 119.9 . . ?
C29 C30 C25 120.7(3) . . ?
C29 C30 H30A 119.7 . . ?
C25 C30 H30A 119.7 . . ?
C4 N1 C2 117.7(2) . . ?
C4 N1 H1C 107.9 . . ?
C2 N1 H1C 107.9 . . ?
C4 N1 H1B 107.9 . . ?
C2 N1 H1B 107.9 . . ?
H1C N1 H1B 107.2 . . ?
C14 N11 C12 114.4(2) . . ?
C14 N11 H11C 108.6 . . ?
C12 N11 H11C 108.6 . . ?
C14 N11 H11B 108.6 . . ?
C12 N11 H11B 108.6 . . ?
H11C N11 H11B 107.6 . . ?
C24 N21 C22 115.0(2) . . ?
C24 N21 H21C 108.5 . . ?
C22 N21 H21C 108.5 . . ?
C24 N21 H21B 108.5 . . ?
C22 N21 H21B 108.5 . . ?
H21C N21 H21B 107.5 . . ?
C1 O1 H1 109.5 . . ?
C11 O11 H11 109.5 . . ?
C21 O21 H21 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 49.2(3) . . . . ?
C5 C1 C2 N1 178.6(2) . . . . ?
O1 C1 C2 C3 -70.5(3) . . . . ?
C5 C1 C2 C3 58.9(3) . . . . ?
O1 C1 C5 C10 -141.8(2) . . . . ?
C2 C1 C5 C10 91.2(3) . . . . ?
O1 C1 C5 C6 38.3(3) . . . . ?
C2 C1 C5 C6 -88.7(3) . . . . ?
C10 C5 C6 C7 -0.6(4) . . . . ?
C1 C5 C6 C7 179.3(3) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C8 C9 C10 C5 -0.5(5) . . . . ?
C6 C5 C10 C9 0.8(4) . . . . ?
C1 C5 C10 C9 -179.1(3) . . . . ?
O11 C11 C12 N11 64.4(3) . . . . ?
C15 C11 C12 N11 -171.5(2) . . . . ?
O11 C11 C12 C13 -59.2(3) . . . . ?
C15 C11 C12 C13 64.8(3) . . . . ?
O11 C11 C15 C20 -170.0(2) . . . . ?
C12 C11 C15 C20 69.4(3) . . . . ?
O11 C11 C15 C16 11.9(3) . . . . ?
C12 C11 C15 C16 -108.8(3) . . . . ?
C20 C15 C16 C17 0.2(5) . . . . ?
C11 C15 C16 C17 178.3(3) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C16 C17 C18 C19 -0.4(6) . . . . ?
C17 C18 C19 C20 1.1(5) . . . . ?
C16 C15 C20 C19 0.6(5) . . . . ?
C11 C15 C20 C19 -177.6(3) . . . . ?
C18 C19 C20 C15 -1.2(5) . . . . ?
O21 C21 C22 N21 69.8(3) . . . . ?
C25 C21 C22 N21 -165.0(2) . . . . ?
O21 C21 C22 C23 -52.2(3) . . . . ?
C25 C21 C22 C23 73.0(3) . . . . ?
O21 C21 C25 C26 13.3(4) . . . . ?
C22 C21 C25 C26 -107.0(3) . . . . ?
O21 C21 C25 C30 -167.1(2) . . . . ?
C22 C21 C25 C30 72.6(3) . . . . ?
C30 C25 C26 C27 -0.2(4) . . . . ?
C21 C25 C26 C27 179.4(3) . . . . ?
C25 C26 C27 C28 0.5(5) . . . . ?
C26 C27 C28 C29 -0.4(5) . . . . ?
C27 C28 C29 C30 0.2(5) . . . . ?
C28 C29 C30 C25 0.0(4) . . . . ?
C26 C25 C30 C29 0.0(4) . . . . ?
C21 C25 C30 C29 -179.6(2) . . . . ?
C3 C2 N1 C4 177.6(2) . . . . ?
C1 C2 N1 C4 52.8(3) . . . . ?
C13 C12 N11 C14 -66.4(3) . . . . ?
C11 C12 N11 C14 168.6(2) . . . . ?
C23 C22 N21 C24 -70.5(3) . . . . ?
C21 C22 N21 C24 165.5(2) . . . . ?

_refine_diff_density_max         0.923
_refine_diff_density_min         -0.898
_refine_diff_density_rms         0.085



_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_mb7_100_a1_180209_ephcl
_database_code_depnum_ccdc_archive 'CCDC 1823199'
_audit_update_record             
;
2018-02-09 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;
_audit_creation_date             2018-02-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H16 N O, Cl'
_chemical_formula_sum            'C10 H16 Cl N O'
_chemical_formula_weight         201.69
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2565(3)
_cell_length_b                   6.1232(3)
_cell_length_c                   12.5570(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.256(5)
_cell_angle_gamma                90
_cell_volume                     545.23(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5651
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      33.1270
_cell_measurement_theta_min      2.8520
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7304
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.767
_diffrn_reflns_theta_min         2.873
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.00(10)
_diffrn_detector                 'HPC detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  82.00   0.50   15.00    --    9.96  57.00 -30.00  174
  2  ω     55.00  90.00   0.50   15.00    --    9.96  19.00 -60.00   70
  3  ω     -5.00  77.00   0.50   15.00    --    9.96  57.00  90.00  164
  4  ω     -1.00  50.00   0.50   15.00    --    9.96  19.00 -60.00  102
  5  ω     -5.00  21.00   0.50   15.00    --    9.96 -57.00 -30.00   52
  6  ω     -4.00  36.00   0.50   15.00    --    9.96  57.00-120.00   80
  7  ω    -19.00  27.00   0.50   15.00    --  -11.05  57.00-150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0777276000
_diffrn_orient_matrix_UB_12      0.0666744000
_diffrn_orient_matrix_UB_13      -0.0239620000
_diffrn_orient_matrix_UB_21      0.0257411000
_diffrn_orient_matrix_UB_22      -0.0092890000
_diffrn_orient_matrix_UB_23      -0.0512442000
_diffrn_orient_matrix_UB_31      -0.0574739000
_diffrn_orient_matrix_UB_32      -0.0942478000
_diffrn_orient_matrix_UB_33      -0.0118744000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    0.903
_reflns_Friedel_fraction_max     0.681
_reflns_number_gt                2969
_reflns_number_total             3239
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1088 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         3239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0737
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6360(2) 0.5687(3) 0.23272(13) 0.0228(3) Uani 1 1 d . . . . .
H1 H 0.5100 0.6422 0.2156 0.027 Uiso 1 1 calc R . . . .
C2 C 0.7806(2) 0.7190(3) 0.19656(12) 0.0209(3) Uani 1 1 d . . . . .
H2 H 0.8054 0.8461 0.2476 0.025 Uiso 1 1 calc R . . . .
C3 C 0.9675(2) 0.6051(3) 0.19615(14) 0.0259(3) Uani 1 1 d . . . . .
H3A H 0.9471 0.4887 0.1413 0.039 Uiso 1 1 calc GR . . . .
H3B H 1.0177 0.5421 0.2682 0.039 Uiso 1 1 calc GR . . . .
H3C H 1.0576 0.7114 0.1787 0.039 Uiso 1 1 calc GR . . . .
C4 C 0.8017(2) 0.9822(3) 0.04500(14) 0.0287(4) Uani 1 1 d . . . . .
H4A H 0.9280 0.9301 0.0415 0.043 Uiso 1 1 calc GR . . . .
H4B H 0.8126 1.1060 0.0954 0.043 Uiso 1 1 calc GR . . . .
H4C H 0.7351 1.0286 -0.0277 0.043 Uiso 1 1 calc GR . . . .
C5 C 0.68921(18) 0.5280(4) 0.35430(11) 0.0220(3) Uani 1 1 d . . . . .
C6 C 0.7837(2) 0.3407(3) 0.39852(14) 0.0278(4) Uani 1 1 d . . . . .
H6 H 0.8142 0.2307 0.3518 0.033 Uiso 1 1 calc R . . . .
C7 C 0.8336(3) 0.3137(3) 0.51051(15) 0.0345(4) Uani 1 1 d . . . . .
H7 H 0.8984 0.1854 0.5402 0.041 Uiso 1 1 calc R . . . .
C8 C 0.7895(3) 0.4731(4) 0.57930(14) 0.0353(5) Uani 1 1 d . . . . .
H8 H 0.8240 0.4539 0.6560 0.042 Uiso 1 1 calc R . . . .
C9 C 0.6955(3) 0.6598(4) 0.53647(15) 0.0346(4) Uani 1 1 d . . . . .
H9 H 0.6651 0.7689 0.5837 0.042 Uiso 1 1 calc R . . . .
C10 C 0.6454(2) 0.6877(3) 0.42426(14) 0.0284(4) Uani 1 1 d . . . . .
H10 H 0.5810 0.8165 0.3949 0.034 Uiso 1 1 calc R . . . .
N1 N 0.69461(19) 0.8025(2) 0.08424(11) 0.0228(3) Uani 1 1 d . . . . .
H1A H 0.6846 0.6893 0.0364 0.027 Uiso 1 1 calc R . . . .
H1B H 0.5759 0.8508 0.0839 0.027 Uiso 1 1 calc R . . . .
O1 O 0.62683(18) 0.3776(2) 0.16754(10) 0.0319(3) Uani 1 1 d . . . . .
H1C H 0.5315 0.3041 0.1729 0.048 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.32072(5) 0.02128(6) 0.12626(3) 0.02512(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 1.0000 . ?
C1 C2 1.535(2) . ?
C1 C5 1.514(2) . ?
C1 O1 1.4214(19) . ?
C2 H2 1.0000 . ?
C2 C3 1.526(2) . ?
C2 N1 1.506(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 N1 1.490(2) . ?
C5 C6 1.390(3) . ?
C5 C10 1.395(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(2) . ?
C10 H10 0.9500 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
O1 H1C 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 108.5 . . ?
C5 C1 H1 108.5 . . ?
C5 C1 C2 110.65(13) . . ?
O1 C1 H1 108.5 . . ?
O1 C1 C2 105.91(12) . . ?
O1 C1 C5 114.58(14) . . ?
C1 C2 H2 108.6 . . ?
C3 C2 C1 113.03(14) . . ?
C3 C2 H2 108.6 . . ?
N1 C2 C1 107.91(12) . . ?
N1 C2 H2 108.6 . . ?
N1 C2 C3 110.12(12) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
C6 C5 C1 122.49(16) . . ?
C6 C5 C10 119.05(14) . . ?
C10 C5 C1 118.43(17) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.28(16) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.24(17) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.08(16) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.90(17) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 119.8 . . ?
C9 C10 C5 120.45(16) . . ?
C9 C10 H10 119.8 . . ?
C2 N1 H1A 108.6 . . ?
C2 N1 H1B 108.6 . . ?
C4 N1 C2 114.79(12) . . ?
C4 N1 H1A 108.6 . . ?
C4 N1 H1B 108.6 . . ?
H1A N1 H1B 107.5 . . ?
C1 O1 H1C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1 0.91 2.28 3.1370(14) 156.8 2_655
N1 H1B Cl1 0.91 2.28 3.1688(14) 163.9 1_565
O1 H1C Cl1 0.84 2.30 3.0782(12) 153.7 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N1 C4 169.31(13) . . . . ?
C1 C5 C6 C7 178.33(15) . . . . ?
C1 C5 C10 C9 -178.51(15) . . . . ?
C2 C1 C5 C6 -98.24(19) . . . . ?
C2 C1 C5 C10 80.18(17) . . . . ?
C3 C2 N1 C4 -66.90(18) . . . . ?
C5 C1 C2 C3 73.37(17) . . . . ?
C5 C1 C2 N1 -164.62(13) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C5 C10 C9 0.0(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C5 0.1(3) . . . . ?
C10 C5 C6 C7 -0.1(2) . . . . ?
O1 C1 C2 C3 -51.37(17) . . . . ?
O1 C1 C2 N1 70.65(16) . . . . ?
O1 C1 C5 C6 21.4(2) . . . . ?
O1 C1 C5 C10 -160.17(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.623
####################################################################### 
# 
# 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_MB7_100_A10_180202_EphSCN
_database_code_depnum_ccdc_archive 'CCDC 1823201'
_audit_update_record             
;
2018-02-09 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H16 N2 O S'
_chemical_formula_weight         224.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   6.09862(6)
_cell_length_b                   7.52704(9)
_cell_length_c                   27.3811(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1256.92(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    8422
_cell_measurement_theta_min      5.975
_cell_measurement_theta_max      78.498

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.107
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10879
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.228
_diffrn_reflns_theta_max         78.698
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2659
_reflns_number_gt                2582
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.992

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Rigaku, 2015)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku, 2015)'
_computing_data_reduction        'CrysAlis PRO (Rigaku, 2015)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+0.2525P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1018 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(6)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2659
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1016(3) 0.4779(2) 0.36834(6) 0.0274(3) Uani 1 1 d . . . . .
H1 H -0.0338 0.5928 0.3580 0.033 Uiso 1 1 calc R U . . .
C2 C 0.0495(3) 0.3262(2) 0.35241(5) 0.0259(3) Uani 1 1 d . . . . .
H2 H 0.1928 0.3381 0.3698 0.031 Uiso 1 1 calc R U . . .
C3 C -0.0434(3) 0.1430(2) 0.36222(6) 0.0337(4) Uani 1 1 d . . . . .
H3A H -0.1814 0.1286 0.3443 0.051 Uiso 1 1 calc R U . . .
H3B H -0.0705 0.1292 0.3973 0.051 Uiso 1 1 calc R U . . .
H3C H 0.0616 0.0527 0.3514 0.051 Uiso 1 1 calc R U . . .
C4 C 0.2794(3) 0.2502(3) 0.27819(7) 0.0359(4) Uani 1 1 d . . . . .
H4A H 0.2596 0.1226 0.2838 0.054 Uiso 1 1 calc R U . . .
H4B H 0.4136 0.2903 0.2945 0.054 Uiso 1 1 calc R U . . .
H4C H 0.2911 0.2731 0.2430 0.054 Uiso 1 1 calc R U . . .
C5 C -0.1344(3) 0.4826(2) 0.42323(6) 0.0276(3) Uani 1 1 d . . . . .
C6 C -0.3150(3) 0.4035(3) 0.44525(7) 0.0342(4) Uani 1 1 d . . . . .
H6 H -0.4214 0.3444 0.4258 0.041 Uiso 1 1 calc R U . . .
C7 C -0.3405(4) 0.4107(3) 0.49568(7) 0.0406(5) Uani 1 1 d . . . . .
H7 H -0.4642 0.3563 0.5105 0.049 Uiso 1 1 calc R U . . .
C8 C -0.1874(4) 0.4962(3) 0.52419(7) 0.0411(4) Uani 1 1 d . . . . .
H8 H -0.2055 0.5006 0.5586 0.049 Uiso 1 1 calc R U . . .
C9 C -0.0071(4) 0.5760(3) 0.50262(7) 0.0420(5) Uani 1 1 d . . . . .
H9 H 0.0985 0.6353 0.5222 0.050 Uiso 1 1 calc R U . . .
C10 C 0.0192(3) 0.5690(3) 0.45228(6) 0.0354(4) Uani 1 1 d . . . . .
H10 H 0.1431 0.6237 0.4376 0.042 Uiso 1 1 calc R U . . .
C11 C 0.3143(3) 0.7661(2) 0.30725(6) 0.0278(3) Uani 1 1 d . . . . .
N12 N 0.0878(2) 0.34868(19) 0.29833(5) 0.0253(3) Uani 1 1 d . . . . .
H12B H -0.0348 0.3126 0.2822 0.030 Uiso 1 1 calc R U . . .
H12A H 0.1064 0.4664 0.2920 0.030 Uiso 1 1 calc R U . . .
N11 N 0.2039(3) 0.7176(2) 0.27535(6) 0.0343(3) Uani 1 1 d . . . . .
O1 O -0.2999(2) 0.45418(19) 0.34178(4) 0.0349(3) Uani 1 1 d . . . . .
H1A H -0.3789 0.5449 0.3449 0.052 Uiso 1 1 calc R U . . .
S11 S 0.46917(8) 0.83266(7) 0.35233(2) 0.04021(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.422(2) . ?
C1 C5 1.516(2) . ?
C1 C2 1.531(2) . ?
C1 H1 1.0000 . ?
C2 N12 1.5085(19) . ?
C2 C3 1.515(2) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N12 1.490(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.389(3) . ?
C5 C10 1.391(2) . ?
C6 C7 1.391(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 N11 1.162(2) . ?
C11 S11 1.6330(19) . ?
N12 H12B 0.9100 . ?
N12 H12A 0.9100 . ?
O1 H1A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C5 113.43(15) . . ?
O1 C1 C2 105.82(13) . . ?
C5 C1 C2 112.29(14) . . ?
O1 C1 H1 108.4 . . ?
C5 C1 H1 108.4 . . ?
C2 C1 H1 108.4 . . ?
N12 C2 C3 109.52(13) . . ?
N12 C2 C1 106.82(12) . . ?
C3 C2 C1 113.76(14) . . ?
N12 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N12 C4 H4A 109.5 . . ?
N12 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N12 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 119.09(16) . . ?
C6 C5 C1 121.65(16) . . ?
C10 C5 C1 119.27(16) . . ?
C5 C6 C7 120.20(18) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.35(19) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.95(17) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 119.90(18) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 120.51(18) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
N11 C11 S11 179.49(17) . . ?
C4 N12 C2 115.41(13) . . ?
C4 N12 H12B 108.4 . . ?
C2 N12 H12B 108.4 . . ?
C4 N12 H12A 108.4 . . ?
C2 N12 H12A 108.4 . . ?
H12B N12 H12A 107.5 . . ?
C1 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N12 61.80(16) . . . . ?
C5 C1 C2 N12 -173.95(14) . . . . ?
O1 C1 C2 C3 -59.17(17) . . . . ?
C5 C1 C2 C3 65.08(19) . . . . ?
O1 C1 C5 C6 23.9(2) . . . . ?
C2 C1 C5 C6 -96.0(2) . . . . ?
O1 C1 C5 C10 -155.70(16) . . . . ?
C2 C1 C5 C10 84.4(2) . . . . ?
C10 C5 C6 C7 -0.2(3) . . . . ?
C1 C5 C6 C7 -179.81(18) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
C6 C5 C10 C9 0.2(3) . . . . ?
C1 C5 C10 C9 179.76(18) . . . . ?
C3 C2 N12 C4 -73.84(18) . . . . ?
C1 C2 N12 C4 162.53(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N12 H12B N11 0.91 2.01 2.865(2) 155.0 4_545
N12 H12A N11 0.91 2.03 2.934(2) 169.8 .
O1 H1A S11 0.84 2.36 3.1911(14) 168.0 1_455

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.032



####################################################################### 
# 
# 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_I_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 1585752'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   22.3684(7)
_cell_length_b                   8.41560(10)
_cell_length_c                   15.6852(4)
_cell_angle_alpha                90
_cell_angle_beta                 130.585(5)
_cell_angle_gamma                90
_cell_volume                     2242.35(19)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
Sb -0.0562 5.8946 19.6418 5.3034 19.0455 0.4607 5.0371 27.9074 2.6827 75.2825
4.5909 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
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'
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'


_cell_formula_units_Z            2

# Given Formula = C84 H92 N8 O32 Sb2 
# Dc =      2.92 Fooo =   2020.00 Mu =    110.35 M =   1969.19
# Found Formula = C42 H46.00 N4 O16 Sb2 
# Dc =      1.64 FOOO =   1111.99 Mu =    102.00 M =   1106.34

_chemical_formula_sum            'C42 H46 N4 O16 Sb2'
_chemical_formula_moiety         'C8 H4 O12 Sb2, 2(C17 H19 N2 O), 2(H2 O)'
_chemical_compound_source        ?
_chemical_formula_weight         1106.34


_cell_measurement_reflns_used    19256
_cell_measurement_theta_min      4
_cell_measurement_theta_max      79
_cell_measurement_temperature    160

_exptl_crystal_description       lath
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.011
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_max          0.391

_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1111.995
_exptl_absorpt_coefficient_mu    10.200

# Sheldrick geometric approximatio 0.74 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.25
_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     1.54180
_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    'SIR92 (Altomare et al., 1994)'
_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      160
_diffrn_reflns_number            22761
_reflns_number_total             4676
_diffrn_reflns_av_R_equivalents  0.066
# Number of reflections without Friedels Law is 4676 
# Number of reflections with Friedels Law is 2581 
# Theoretical number of reflections is about 2423 


_diffrn_reflns_theta_min         3.711
_diffrn_reflns_theta_max         78.973
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        77.394
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -28
_reflns_limit_h_max              21
_reflns_limit_k_min              -9
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   2.20
_oxford_diffrn_Wilson_scale      0.30

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

_refine_diff_density_min         -0.68
_refine_diff_density_max         2.37


# 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         4676
_refine_ls_number_restraints     5
_refine_ls_number_parameters     290
_oxford_refine_ls_R_factor_ref   0.0458
_refine_ls_wR_factor_ref         0.1194
_refine_ls_goodness_of_fit_ref   0.9417
_refine_ls_shift/su_max          0.0003471
_refine_ls_shift/su_mean         0.0000159


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4676
_refine_ls_R_factor_all          0.0458
_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                4563
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_gt          0.1189

_refine_ls_abs_structure_Flack   -0.010(9)
_refine_ls_abs_structure_details 'Flack (1983), 2095 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) + ( 0.11P)² + 5.88P] 
 ,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 0.5148(3) 0.2301(5) 0.3765(4) 0.0317 1.0000 Uani D . . . . .
C2 C 0.4675(3) 0.2349(7) 0.2525(5) 0.0334 1.0000 Uani . . . . . .
C3 C 0.5186(3) 0.2011(7) 0.2223(4) 0.0336 1.0000 Uani . . . . . .
C4 C 0.5883(3) 0.3081(7) 0.2785(5) 0.0327 1.0000 Uani . . . . . .
C5 C 0.6644(3) 0.2682(7) 0.3625(5) 0.0359 1.0000 Uani . . . . . .
N6 N 0.7118(3) 0.3978(6) 0.3941(4) 0.0365 1.0000 Uani . . . . . .
C7 C 0.6666(3) 0.5251(7) 0.3301(5) 0.0315 1.0000 Uani . . . . . .
C8 C 0.5870(3) 0.4730(6) 0.2542(4) 0.0300 1.0000 Uani . . . . . .
C9 C 0.6870(3) 0.6805(11) 0.3311(4) 0.0356 1.0000 Uani . . . . . .
C10 C 0.6276(4) 0.7872(7) 0.2570(6) 0.0382 1.0000 Uani . . . . . .
C11 C 0.5481(4) 0.7367(8) 0.1789(6) 0.0358 1.0000 Uani . . . . . .
C12 C 0.5269(3) 0.5813(7) 0.1763(5) 0.0292 1.0000 Uani . . . . . .
O13 O 0.4967(3) 0.8560(5) 0.1112(4) 0.0434 1.0000 Uani . . . . . .
C14 C 0.4155(4) 0.8214(8) 0.0235(6) 0.0429 1.0000 Uani . . . . . .
C15 C 0.3724(3) 0.9775(8) -0.0211(5) 0.0380 1.0000 Uani . . . . . .
C16 C 0.3235(4) 1.0256(8) 0.0011(6) 0.0449 1.0000 Uani . . . . . .
C17 C 0.2900(3) 1.1760(16) -0.0306(5) 0.0550 1.0000 Uani . . . . . .
C18 C 0.3002(4) 1.2769(10) -0.0889(7) 0.0563 1.0000 Uani . . . . . .
C19 C 0.3479(5) 1.2293(9) -0.1129(6) 0.0490 1.0000 Uani . . . . . .
C20 C 0.3838(4) 1.0813(8) -0.0784(5) 0.0420 1.0000 Uani . . . . . .
Sb21 Sb 0.420014(14) 0.67703(12) 0.289087(19) 0.0285 1.0000 Uani D . . . . .
O22 O 0.4970(2) 0.8780(4) 0.3503(3) 0.0322 1.0000 Uani . . . . . .
O23 O 0.5233(2) 0.5787(4) 0.4089(3) 0.0275 1.0000 Uani . . . . . .
C24 C 0.5913(2) 0.6745(9) 0.4639(4) 0.0280 1.0000 Uani . . . . . .
C25 C 0.5702(3) 0.8473(7) 0.4233(5) 0.0304 1.0000 Uani . . . . . .
O26 O 0.6219(2) 0.9485(5) 0.4632(4) 0.0350 1.0000 Uani . . . . . .
O27 O 0.3796(2) 0.4731(5) 0.3170(3) 0.0347 1.0000 Uani D . . . . .
O28 O 0.3950(2) 0.7706(4) 0.3784(3) 0.0309 1.0000 Uani . . . . . .
C29 C 0.6391(2) 0.6691(10) 0.5916(4) 0.0285 1.0000 Uani . . . . . .
C30 C 0.3570(3) 0.4970(6) 0.3740(5) 0.0319 1.0000 Uani . . . . . .
O31 O 0.3338(3) 0.3908(5) 0.4000(4) 0.0420 1.0000 Uani . . . . . .
O32 O 0.3956(4) 0.1161(6) 0.3704(6) 0.0724 1.0000 Uani D . . . . .
H241 H 0.6242 0.6327 0.4478 0.0340 1.0000 Uiso R . . . . .
H91 H 0.7394 0.7134 0.3810 0.0430 1.0000 Uiso R . . . . .
H32 H 0.5388 0.0941 0.2457 0.0398 1.0000 Uiso R . . . . .
H31 H 0.4859 0.2109 0.1408 0.0399 1.0000 Uiso R . . . . .
H101 H 0.6399 0.8936 0.2597 0.0462 1.0000 Uiso R . . . . .
H291 H 0.6930 0.7055 0.6292 0.0339 1.0000 Uiso R . . . . .
H161 H 0.3130 0.9558 0.0367 0.0537 1.0000 Uiso R . . . . .
H141 H 0.4079 0.7634 -0.0365 0.0511 1.0000 Uiso R . . . . .
H142 H 0.3958 0.7580 0.0532 0.0511 1.0000 Uiso R . . . . .
H191 H 0.3552 1.2984 -0.1525 0.0588 1.0000 Uiso R . . . . .
H171 H 0.2593 1.2085 -0.0128 0.0660 1.0000 Uiso R . . . . .
H51 H 0.6820 0.1680 0.3950 0.0425 1.0000 Uiso R . . . . .
H201 H 0.4157 1.0500 -0.0943 0.0501 1.0000 Uiso R . . . . .
H22 H 0.4425 0.3382 0.2234 0.0400 1.0000 Uiso R . . . . .
H21 H 0.4274 0.1540 0.2200 0.0399 1.0000 Uiso R . . . . .
H121 H 0.4741 0.5500 0.1250 0.0346 1.0000 Uiso R . . . . .
H181 H 0.2760 1.3765 -0.1112 0.0678 1.0000 Uiso R . . . . .
H61 H 0.7621 0.3993 0.4478 0.0440 1.0000 Uiso R . . . . .
H13 H 0.4842 0.2087 0.3921 0.0482 1.0000 Uiso R . . . . .
H12 H 0.5381 0.3227 0.4061 0.0481 1.0000 Uiso R . . . . .
H11 H 0.5514 0.1566 0.4070 0.0477 1.0000 Uiso R . . . . .
H321 H 0.3988 0.1688 0.4170 0.1091 1.0000 Uiso DR . . . . .
H322 H 0.3961 0.0190 0.3726 0.1091 1.0000 Uiso DR . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.799(14)
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 . 1.492(7) yes
N1 . H13 . 0.882 no
N1 . H12 . 0.884 no
N1 . H11 . 0.879 no
C2 . C3 . 1.521(7) yes
C2 . H22 . 0.972 no
C2 . H21 . 0.967 no
C3 . C4 . 1.493(8) yes
C3 . H32 . 0.967 no
C3 . H31 . 0.979 no
C4 . C5 . 1.352(8) yes
C4 . C8 . 1.434(8) yes
C5 . N6 . 1.371(7) yes
C5 . H51 . 0.930 no
N6 . C7 . 1.363(8) yes
N6 . H61 . 0.861 no
C7 . C8 . 1.423(7) yes
C7 . C9 . 1.382(11) yes
C8 . C12 . 1.412(8) yes
C9 . C10 . 1.383(10) yes
C9 . H91 . 0.931 no
C10 . C11 . 1.418(10) yes
C10 . H101 . 0.929 no
C11 . C12 . 1.382(8) yes
C11 . O13 . 1.367(8) yes
C12 . H121 . 0.935 no
O13 . C14 . 1.423(8) yes
C14 . C15 . 1.506(9) yes
C14 . H141 . 0.973 no
C14 . H142 . 0.981 no
C15 . C16 . 1.406(9) yes
C15 . C20 . 1.390(9) yes
C16 . C17 . 1.387(14) yes
C16 . H161 . 0.940 no
C17 . C18 . 1.371(14) yes
C17 . H171 . 0.934 no
C18 . C19 . 1.402(11) yes
C18 . H181 . 0.933 no
C19 . C20 . 1.387(10) yes
C19 . H191 . 0.939 no
C20 . H201 . 0.934 no
Sb21 . O22 . 2.144(4) yes
Sb21 . O23 . 1.976(3) yes
Sb21 . O27 . 2.115(4) yes
Sb21 . O28 . 1.979(4) yes
O22 . C25 . 1.272(7) yes
O23 . C24 . 1.415(6) yes
C24 . C25 . 1.534(9) yes
C24 . C29 . 1.540(6) yes
C24 . H241 . 0.985 no
C25 . O26 . 1.231(7) yes
O27 . C30 . 1.296(7) yes
O28 . C29 3_656 1.414(7) yes
C29 . C30 3_656 1.529(10) yes
C29 . H291 . 0.985 no
C30 . O31 . 1.229(7) yes
O32 . H321 . 0.817 no
O32 . H322 . 0.818 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 . H13 . 110.3 no
C2 . N1 . H12 . 109.7 no
H13 . N1 . H12 . 109.4 no
C2 . N1 . H11 . 110.3 no
H13 . N1 . H11 . 108.9 no
H12 . N1 . H11 . 108.2 no
N1 . C2 . C3 . 111.2(5) yes
N1 . C2 . H22 . 109.9 no
C3 . C2 . H22 . 109.9 no
N1 . C2 . H21 . 107.2 no
C3 . C2 . H21 . 109.4 no
H22 . C2 . H21 . 109.2 no
C2 . C3 . C4 . 114.2(5) yes
C2 . C3 . H32 . 108.4 no
C4 . C3 . H32 . 106.7 no
C2 . C3 . H31 . 108.5 no
C4 . C3 . H31 . 109.0 no
H32 . C3 . H31 . 110.0 no
C3 . C4 . C5 . 126.5(5) yes
C3 . C4 . C8 . 126.4(5) yes
C5 . C4 . C8 . 107.1(5) yes
C4 . C5 . N6 . 110.1(5) yes
C4 . C5 . H51 . 125.2 no
N6 . C5 . H51 . 124.8 no
C5 . N6 . C7 . 109.3(5) yes
C5 . N6 . H61 . 125.2 no
C7 . N6 . H61 . 125.5 no
N6 . C7 . C8 . 107.4(5) yes
N6 . C7 . C9 . 130.9(5) yes
C8 . C7 . C9 . 121.7(5) yes
C4 . C8 . C7 . 106.2(5) yes
C4 . C8 . C12 . 134.2(5) yes
C7 . C8 . C12 . 119.6(5) yes
C7 . C9 . C10 . 118.4(5) yes
C7 . C9 . H91 . 121.1 no
C10 . C9 . H91 . 120.6 no
C9 . C10 . C11 . 120.7(6) yes
C9 . C10 . H101 . 119.6 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C12 . 121.5(6) yes
C10 . C11 . O13 . 113.5(5) yes
C12 . C11 . O13 . 125.0(6) yes
C8 . C12 . C11 . 118.0(5) yes
C8 . C12 . H121 . 121.4 no
C11 . C12 . H121 . 120.5 no
C11 . O13 . C14 . 120.0(5) yes
O13 . C14 . C15 . 107.4(5) yes
O13 . C14 . H141 . 110.4 no
C15 . C14 . H141 . 109.4 no
O13 . C14 . H142 . 109.8 no
C15 . C14 . H142 . 110.2 no
H141 . C14 . H142 . 109.6 no
C14 . C15 . C16 . 120.1(6) yes
C14 . C15 . C20 . 121.2(6) yes
C16 . C15 . C20 . 118.6(6) yes
C15 . C16 . C17 . 120.0(7) yes
C15 . C16 . H161 . 120.2 no
C17 . C16 . H161 . 119.8 no
C16 . C17 . C18 . 121.2(7) yes
C16 . C17 . H171 . 119.4 no
C18 . C17 . H171 . 119.4 no
C17 . C18 . C19 . 119.2(8) yes
C17 . C18 . H181 . 120.0 no
C19 . C18 . H181 . 120.8 no
C18 . C19 . C20 . 120.0(7) yes
C18 . C19 . H191 . 119.4 no
C20 . C19 . H191 . 120.6 no
C15 . C20 . C19 . 120.9(6) yes
C15 . C20 . H201 . 119.3 no
C19 . C20 . H201 . 119.8 no
O22 . Sb21 . O23 . 78.66(14) yes
O22 . Sb21 . O27 . 151.02(15) yes
O23 . Sb21 . O27 . 81.71(15) yes
O22 . Sb21 . O28 . 83.32(15) yes
O23 . Sb21 . O28 . 100.78(15) yes
O27 . Sb21 . O28 . 79.65(15) yes
Sb21 . O22 . C25 . 115.5(3) yes
Sb21 . O23 . C24 . 118.0(3) yes
O23 . C24 . C25 . 111.6(4) yes
O23 . C24 . C29 . 109.7(4) yes
C25 . C24 . C29 . 109.5(5) yes
O23 . C24 . H241 . 109.1 no
C25 . C24 . H241 . 108.2 no
C29 . C24 . H241 . 108.7 no
C24 . C25 . O22 . 115.8(4) yes
C24 . C25 . O26 . 120.7(5) yes
O22 . C25 . O26 . 123.4(5) yes
Sb21 . O27 . C30 . 115.3(3) yes
C29 3_656 O28 . Sb21 . 117.2(4) yes
C24 . C29 . C30 3_656 108.6(6) yes
C24 . C29 . O28 3_656 110.3(4) yes
C30 3_656 C29 . O28 3_656 112.0(4) yes
C24 . C29 . H291 . 108.2 no
C30 3_656 C29 . H291 . 108.5 no
O28 3_656 C29 . H291 . 109.2 no
C29 3_656 C30 . O27 . 115.6(4) yes
C29 3_656 C30 . O31 . 120.7(5) yes
O27 . C30 . O31 . 123.7(5) yes
H321 . O32 . H322 . 120.8 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
C9 . H91 . O31 2_555 143 0.93 2.44 3.234(10) yes
N6 . H61 . O26 4_646 161 0.86 2.03 2.862(10) yes
N1 . H13 . O32 . 157 0.88 1.94 2.776(10) yes
N1 . H12 . O23 . 147 0.88 2.18 2.963(10) yes
N1 . H12 . O31 3_656 130 0.88 2.54 3.184(10) yes
N1 . H11 . O26 1_545 169 0.88 2.13 2.994(10) yes
O32 . H321 . N1 3_656 144 0.82 2.52 3.216(10) yes
O32 . H321 . O31 . 132 0.82 2.27 2.881(10) yes
O32 . H322 . O28 1_545 179 0.82 2.09 2.911(10) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_I_CCDC10
_database_code_depnum_ccdc_archive 'CCDC 1585762'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_I                   
;
PROBLEM: D-H Without Acceptor O5 --H51 . Please Check
RESPONSE: There is only one potential hydrogen bond acceptor
in the whole structure (nitrile) and this one is far away from
the hydroxy group.
;
# end Validation Reply Form

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.1433(4)
_cell_length_b                   18.6189(6)
_cell_length_c                   14.0467(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.569(3)
_cell_angle_gamma                90
_cell_volume                     2615.91(16)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 0.0033 0.0016 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'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 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 0.0106 0.0060 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'


_cell_formula_units_Z            4

# Given Formula = C31 H35 B1 N2 O1 
# Dc =      1.17 Fooo =    992.00 Mu =      0.70 M =    462.44
# Found Formula = C31 H35 B1 N2 O1 
# Dc =      1.17 FOOO =    992.00 Mu =      0.70 M =    462.44

_chemical_formula_sum            'C31 H35 B N2 O'
_chemical_formula_moiety         'C24 H20 B, C7 H15 N2 O'
_chemical_compound_source        ?
_chemical_formula_weight         462.44


_cell_measurement_reflns_used    10015
_cell_measurement_theta_min      3
_cell_measurement_theta_max      33
_cell_measurement_temperature    160

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.052
_exptl_crystal_size_mid          0.459
_exptl_crystal_size_max          0.482

_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             992.000
_exptl_absorpt_coefficient_mu    0.070

# Sheldrick geometric approximatio 0.97 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_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    'USER DEFINED STRUCTURE SOLUTION'
_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      160
_diffrn_reflns_number            33386
_reflns_number_total             7988
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 7988 
# Theoretical number of reflections is about 15968 


_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         30.505
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        30.505
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              26
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.46
_refine_diff_density_max         0.47


# 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>-2.0\s(I)
_refine_ls_number_reflns         7983
_refine_ls_number_restraints     128
_refine_ls_number_parameters     407
_oxford_refine_ls_R_factor_ref   0.0720
_refine_ls_wR_factor_ref         0.1478
_refine_ls_goodness_of_fit_ref   1.0133
_refine_ls_shift/su_max          0.0004149
_refine_ls_shift/su_mean         0.0000420


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7988
_refine_ls_R_factor_all          0.0721
_refine_ls_wR_factor_all         0.1480

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6470
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_gt          0.1365

# 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 .


_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) + ( 0.06P)² + 1.11P] 
 ,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
N21 N 0.6606(15) 0.5583(7) 0.4775(8) 0.0559 0.210(4) Uani D . P 1 2 .
C22 C 0.677(4) 0.5053(14) 0.5101(17) 0.0477 0.210(4) Uani D . P 1 2 .
C24 C 0.7047(10) 0.4336(5) 0.6622(6) 0.0390 0.210(4) Uani D . P 1 2 .
C26 C 0.6961(10) 0.3604(5) 0.6961(6) 0.0465 0.210(4) Uani D . P 1 2 .
N27 N 0.6506(11) 0.3491(5) 0.7866(7) 0.0455 0.210(4) Uani D . P 1 2 .
C28 C 0.6813(17) 0.2767(8) 0.7972(11) 0.0959 0.210(4) Uani D . P 1 2 .
C29 C 0.5089(13) 0.3639(10) 0.7849(11) 0.0857 0.210(4) Uani D . P 1 2 .
C30 C 0.715(2) 0.3887(15) 0.8674(19) 0.0481 0.210(4) Uani D . P 1 2 .
N1 N 0.6326(4) 0.55874(19) 0.5125(2) 0.0546 0.790(4) Uani D . P 1 1 .
C2 C 0.6708(8) 0.5016(4) 0.5281(4) 0.0417 0.790(4) Uani D . P 1 1 .
C3 C 0.7061(4) 0.4269(2) 0.5451(3) 0.0437 0.790(4) Uani D . P 1 1 .
C4 C 0.7441(3) 0.40951(13) 0.65435(17) 0.0416 0.790(4) Uani D . P 1 1 .
O5 O 0.8295(4) 0.4626(2) 0.7045(3) 0.0633 0.790(4) Uani D . P 1 1 .
C6 C 0.61474(17) 0.41074(9) 0.69535(12) 0.0277 0.790(4) Uani D . P 1 1 .
N7 N 0.6169(2) 0.37292(11) 0.79200(14) 0.0275 0.790(4) Uani D . P 1 1 .
C8 C 0.4900(2) 0.39409(14) 0.82751(19) 0.0452 0.790(4) Uani D . P 1 1 .
C9 C 0.6134(3) 0.29313(12) 0.78114(19) 0.0461 0.790(4) Uani D . P 1 1 .
C10 C 0.7354(5) 0.3957(4) 0.8666(4) 0.0366 0.790(4) Uani D . P 1 1 .
B600 B 0.20318(12) 0.60499(7) 0.78099(9) 0.0187 1.0000 Uani . . . . . .
C601 C 0.14305(12) 0.65913(6) 0.85551(8) 0.0206 1.0000 Uani . . . . . .
C602 C 0.21663(14) 0.71501(7) 0.90569(10) 0.0309 1.0000 Uani . . . . . .
C603 C 0.16156(18) 0.76229(8) 0.96539(12) 0.0408 1.0000 Uani . . . . . .
C604 C 0.03040(18) 0.75480(8) 0.97776(10) 0.0384 1.0000 Uani . . . . . .
C605 C -0.04666(16) 0.70145(7) 0.92786(11) 0.0338 1.0000 Uani . . . . . .
C606 C 0.00888(13) 0.65505(7) 0.86749(10) 0.0265 1.0000 Uani . . . . . .
C607 C 0.15770(11) 0.52142(6) 0.79483(8) 0.0193 1.0000 Uani . . . . . .
C608 C 0.11885(12) 0.49622(7) 0.87998(9) 0.0240 1.0000 Uani . . . . . .
C609 C 0.09063(13) 0.42428(7) 0.89506(10) 0.0290 1.0000 Uani . . . . . .
C610 C 0.10141(13) 0.37375(7) 0.82464(11) 0.0307 1.0000 Uani . . . . . .
C611 C 0.14143(15) 0.39586(7) 0.73956(11) 0.0328 1.0000 Uani . . . . . .
C612 C 0.16899(13) 0.46838(7) 0.72556(9) 0.0274 1.0000 Uani . . . . . .
C613 C 0.36773(11) 0.60249(6) 0.80393(8) 0.0208 1.0000 Uani . . . . . .
C614 C 0.45246(13) 0.61114(8) 0.73577(10) 0.0293 1.0000 Uani . . . . . .
C615 C 0.59139(14) 0.60511(9) 0.75936(12) 0.0374 1.0000 Uani . . . . . .
C616 C 0.65034(13) 0.58983(8) 0.85260(12) 0.0377 1.0000 Uani . . . . . .
C617 C 0.57062(14) 0.57983(8) 0.92233(11) 0.0355 1.0000 Uani . . . . . .
C618 C 0.43263(13) 0.58590(8) 0.89761(9) 0.0281 1.0000 Uani . . . . . .
C619 C 0.14571(11) 0.63761(6) 0.67386(8) 0.0215 1.0000 Uani . . . . . .
C620 C 0.03649(13) 0.60969(8) 0.61096(10) 0.0309 1.0000 Uani . . . . . .
C621 C -0.01284(15) 0.64154(10) 0.52233(11) 0.0424 1.0000 Uani . . . . . .
C622 C 0.04556(15) 0.70317(9) 0.49339(11) 0.0396 1.0000 Uani . . . . . .
C623 C 0.15043(14) 0.73395(8) 0.55493(10) 0.0324 1.0000 Uani . . . . . .
C624 C 0.19826(13) 0.70194(7) 0.64337(9) 0.0269 1.0000 Uani . . . . . .
H6021 H 0.3070 0.7202 0.9002 0.0376 1.0000 Uiso R . . . . .
H6031 H 0.2158 0.7988 0.9991 0.0494 1.0000 Uiso R . . . . .
H6041 H -0.0039 0.7866 1.0187 0.0465 1.0000 Uiso R . . . . .
H6051 H -0.1375 0.6968 0.9330 0.0402 1.0000 Uiso R . . . . .
H6061 H -0.0451 0.6192 0.8334 0.0333 1.0000 Uiso R . . . . .
H6081 H 0.1104 0.5297 0.9296 0.0303 1.0000 Uiso R . . . . .
H6091 H 0.0641 0.4099 0.9539 0.0356 1.0000 Uiso R . . . . .
H6101 H 0.0830 0.3251 0.8350 0.0365 1.0000 Uiso R . . . . .
H6111 H 0.1506 0.3616 0.6899 0.0403 1.0000 Uiso R . . . . .
H6121 H 0.1968 0.4819 0.6667 0.0342 1.0000 Uiso R . . . . .
H6141 H 0.4147 0.6217 0.6715 0.0347 1.0000 Uiso R . . . . .
H6151 H 0.6437 0.6106 0.7097 0.0461 1.0000 Uiso R . . . . .
H6161 H 0.7436 0.5850 0.8693 0.0458 1.0000 Uiso R . . . . .
H6171 H 0.6106 0.5685 0.9874 0.0426 1.0000 Uiso R . . . . .
H6181 H 0.3790 0.5774 0.9454 0.0340 1.0000 Uiso R . . . . .
H6201 H -0.0060 0.5672 0.6294 0.0376 1.0000 Uiso R . . . . .
H6211 H -0.0887 0.6202 0.4828 0.0522 1.0000 Uiso R . . . . .
H6221 H 0.0148 0.7249 0.4323 0.0488 1.0000 Uiso R . . . . .
H6231 H 0.1891 0.7772 0.5366 0.0398 1.0000 Uiso R . . . . .
H6241 H 0.2697 0.7246 0.6844 0.0332 1.0000 Uiso R . . . . .
O25 O 0.8147(13) 0.4736(7) 0.7129(12) 0.0389 0.210(4) Uani D . P 1 2 .
H241 H 0.6307 0.4694 0.6775 0.0510 0.210(4) Uiso R . P 1 2 .
H262 H 0.7836 0.3377 0.6958 0.0540 0.210(4) Uiso R . P 1 2 .
H261 H 0.6319 0.3354 0.6480 0.0541 0.210(4) Uiso R . P 1 2 .
H291 H 0.4831 0.3460 0.8430 0.1229 0.210(4) Uiso R . P 1 2 .
H293 H 0.4920 0.4131 0.7755 0.1230 0.210(4) Uiso R . P 1 2 .
H292 H 0.4574 0.3363 0.7311 0.1227 0.210(4) Uiso R . P 1 2 .
H31 H 0.7891 0.4190 0.5172 0.0529 0.790(4) Uiso R . P 1 1 .
H32 H 0.6365 0.3973 0.5134 0.0514 0.790(4) Uiso R . P 1 1 .
H41 H 0.7859 0.3587 0.6619 0.0489 0.790(4) Uiso R . P 1 1 .
H61 H 0.5892 0.4599 0.7045 0.0337 0.790(4) Uiso R . P 1 1 .
H62 H 0.5435 0.3900 0.6506 0.0351 0.790(4) Uiso R . P 1 1 .
H81 H 0.4868 0.3678 0.8864 0.0687 0.790(4) Uiso R . P 1 1 .
H82 H 0.4911 0.4464 0.8379 0.0691 0.790(4) Uiso R . P 1 1 .
H83 H 0.4138 0.3814 0.7786 0.0679 0.790(4) Uiso R . P 1 1 .
H91 H 0.6170 0.2710 0.8430 0.0672 0.790(4) Uiso R . P 1 1 .
H92 H 0.6976 0.2799 0.7544 0.0695 0.790(4) Uiso R . P 1 1 .
H93 H 0.5317 0.2791 0.7376 0.0695 0.790(4) Uiso R . P 1 1 .
H103 H 0.7223 0.3722 0.9286 0.0543 0.790(4) Uiso R . P 1 1 .
H101 H 0.7365 0.4463 0.8731 0.0538 0.790(4) Uiso R . P 1 1 .
H102 H 0.8174 0.3756 0.8489 0.0539 0.790(4) Uiso R . P 1 1 .
H281 H 0.6549 0.2545 0.7336 0.1400 0.210(4) Uiso R . P 1 2 .
H283 H 0.6558 0.2568 0.8452 0.1397 0.210(4) Uiso R . P 1 2 .
H282 H 0.7851 0.2764 0.8041 0.1399 0.210(4) Uiso R . P 1 2 .
H301 H 0.7127 0.3691 0.9214 0.0648 0.210(4) Uiso R . P 1 2 .
H303 H 0.8001 0.4043 0.8510 0.0649 0.210(4) Uiso R . P 1 2 .
H302 H 0.6601 0.4373 0.8608 0.0650 0.210(4) Uiso R . P 1 2 .
C23 C 0.7468(17) 0.4380(10) 0.5570(13) 0.0473 0.210(4) Uani D . P 1 2 .
H232 H 0.8438 0.4428 0.5662 0.0649 0.210(4) Uiso R . P 1 2 .
H231 H 0.7171 0.3964 0.5214 0.0648 0.210(4) Uiso R . P 1 2 .
H51 H 0.8999 0.4673 0.6799 0.0798 0.790(4) Uiso DR . P 1 1 .
H251 H 0.8872 0.4541 0.7337 0.0799 0.210(4) Uiso DR . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.50(2)
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
N21 . C22 . 1.09(3) yes
C22 . C23 . 1.53(3) yes
C24 . C26 . 1.453(13) yes
C24 . O25 . 1.429(5) yes
C24 . H241 . 1.051 no
C24 . C23 . 1.61(2) yes
C26 . N27 . 1.438(12) yes
C26 . H262 . 0.983 no
C26 . H261 . 0.975 no
N27 . C28 . 1.387(16) yes
N27 . C29 . 1.460(15) yes
N27 . C30 . 1.42(3) yes
C28 . H281 . 0.981 no
C28 . H283 . 0.846 no
C28 . H282 . 1.041 no
C29 . H291 . 0.958 no
C29 . H293 . 0.936 no
C29 . H292 . 0.988 no
C30 . H301 . 0.847 no
C30 . H303 . 0.972 no
C30 . H302 . 1.060 no
N1 . C2 . 1.142(7) yes
C2 . C3 . 1.445(8) yes
C3 . C4 . 1.553(5) yes
C3 . H31 . 0.997 no
C3 . H32 . 0.946 no
C4 . O5 . 1.421(3) yes
C4 . C6 . 1.519(3) yes
C4 . H41 . 1.035 no
O5 . H51 . 0.847 no
C6 . N7 . 1.526(2) yes
C6 . H61 . 0.966 no
C6 . H62 . 0.957 no
N7 . C8 . 1.508(3) yes
N7 . C9 . 1.493(3) yes
N7 . C10 . 1.518(5) yes
C8 . H81 . 0.967 no
C8 . H82 . 0.985 no
C8 . H83 . 0.974 no
C9 . H91 . 0.957 no
C9 . H92 . 1.019 no
C9 . H93 . 0.980 no
C10 . H103 . 1.002 no
C10 . H101 . 0.946 no
C10 . H102 . 0.981 no
B600 . C601 . 1.6421(17) yes
B600 . C607 . 1.6436(17) yes
B600 . C613 . 1.6471(17) yes
B600 . C619 . 1.6375(17) yes
C601 . C602 . 1.4006(17) yes
C601 . C606 . 1.4008(17) yes
C602 . C603 . 1.395(2) yes
C602 . H6021 . 0.937 no
C603 . C604 . 1.377(2) yes
C603 . H6031 . 0.950 no
C604 . C605 . 1.381(2) yes
C604 . H6041 . 0.932 no
C605 . C606 . 1.3935(18) yes
C605 . H6051 . 0.940 no
C606 . H6061 . 0.943 no
C607 . C608 . 1.4010(16) yes
C607 . C612 . 1.4043(17) yes
C608 . C609 . 1.3932(17) yes
C608 . H6081 . 0.950 no
C609 . C610 . 1.383(2) yes
C609 . H6091 . 0.949 no
C610 . C611 . 1.387(2) yes
C610 . H6101 . 0.940 no
C611 . C612 . 1.3995(18) yes
C611 . H6111 . 0.960 no
C612 . H6121 . 0.951 no
C613 . C614 . 1.3982(17) yes
C613 . C618 . 1.4044(17) yes
C614 . C615 . 1.3975(19) yes
C614 . H6141 . 0.941 no
C615 . C616 . 1.376(2) yes
C615 . H6151 . 0.950 no
C616 . C617 . 1.383(2) yes
C616 . H6161 . 0.940 no
C617 . C618 . 1.3895(18) yes
C617 . H6171 . 0.959 no
C618 . H6181 . 0.945 no
C619 . C620 . 1.3975(17) yes
C619 . C624 . 1.4063(17) yes
C620 . C621 . 1.3946(19) yes
C620 . H6201 . 0.957 no
C621 . C622 . 1.383(2) yes
C621 . H6211 . 0.957 no
C622 . C623 . 1.379(2) yes
C622 . H6221 . 0.953 no
C623 . C624 . 1.3906(18) yes
C623 . H6231 . 0.950 no
C624 . H6241 . 0.947 no
O25 . H251 . 0.828 no
C23 . H232 . 0.975 no
C23 . H231 . 0.944 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
N21 . C22 . C23 . 162(3) yes
C26 . C24 . O25 . 114.2(9) yes
C26 . C24 . H241 . 116.4 no
O25 . C24 . H241 . 95.4 no
C26 . C24 . C23 . 112.8(9) yes
O25 . C24 . C23 . 97.3(10) yes
H241 . C24 . C23 . 117.7 no
C24 . C26 . N27 . 118.2(8) yes
C24 . C26 . H262 . 107.4 no
N27 . C26 . H262 . 111.3 no
C24 . C26 . H261 . 106.9 no
N27 . C26 . H261 . 105.5 no
H262 . C26 . H261 . 107.0 no
C26 . N27 . C28 . 97.9(10) yes
C26 . N27 . C29 . 114.7(10) yes
C28 . N27 . C29 . 112.9(12) yes
C26 . N27 . C30 . 117.2(14) yes
C28 . N27 . C30 . 110.7(14) yes
C29 . N27 . C30 . 103.7(14) yes
N27 . C28 . H281 . 106.7 no
N27 . C28 . H283 . 114.7 no
H281 . C28 . H283 . 118.0 no
N27 . C28 . H282 . 102.7 no
H281 . C28 . H282 . 101.6 no
H283 . C28 . H282 . 111.3 no
N27 . C29 . H291 . 109.1 no
N27 . C29 . H293 . 110.1 no
H291 . C29 . H293 . 113.0 no
N27 . C29 . H292 . 107.9 no
H291 . C29 . H292 . 106.6 no
H293 . C29 . H292 . 109.9 no
N27 . C30 . H301 . 114.5 no
N27 . C30 . H303 . 106.0 no
H301 . C30 . H303 . 120.0 no
N27 . C30 . H302 . 102.0 no
H301 . C30 . H302 . 110.6 no
H303 . C30 . H302 . 101.5 no
N1 . C2 . C3 . 174.5(7) yes
C2 . C3 . C4 . 112.2(4) yes
C2 . C3 . H31 . 106.2 no
C4 . C3 . H31 . 105.7 no
C2 . C3 . H32 . 109.7 no
C4 . C3 . H32 . 112.8 no
H31 . C3 . H32 . 110.0 no
C3 . C4 . O5 . 112.0(3) yes
C3 . C4 . C6 . 106.4(2) yes
O5 . C4 . C6 . 107.2(3) yes
C3 . C4 . H41 . 108.8 no
O5 . C4 . H41 . 112.3 no
C6 . C4 . H41 . 109.9 no
C4 . O5 . H51 . 110.9 no
C4 . C6 . N7 . 116.43(15) yes
C4 . C6 . H61 . 109.4 no
N7 . C6 . H61 . 106.5 no
C4 . C6 . H62 . 110.5 no
N7 . C6 . H62 . 107.1 no
H61 . C6 . H62 . 106.3 no
C6 . N7 . C8 . 106.68(17) yes
C6 . N7 . C9 . 111.81(18) yes
C8 . N7 . C9 . 106.66(18) yes
C6 . N7 . C10 . 112.2(3) yes
C8 . N7 . C10 . 108.7(3) yes
C9 . N7 . C10 . 110.5(3) yes
N7 . C8 . H81 . 107.6 no
N7 . C8 . H82 . 108.5 no
H81 . C8 . H82 . 112.0 no
N7 . C8 . H83 . 108.9 no
H81 . C8 . H83 . 110.2 no
H82 . C8 . H83 . 109.4 no
N7 . C9 . H91 . 109.8 no
N7 . C9 . H92 . 105.7 no
H91 . C9 . H92 . 108.8 no
N7 . C9 . H93 . 109.4 no
H91 . C9 . H93 . 110.6 no
H92 . C9 . H93 . 112.3 no
N7 . C10 . H103 . 105.9 no
N7 . C10 . H101 . 109.9 no
H103 . C10 . H101 . 110.6 no
N7 . C10 . H102 . 109.0 no
H103 . C10 . H102 . 107.1 no
H101 . C10 . H102 . 114.0 no
C601 . B600 . C607 . 111.37(9) yes
C601 . B600 . C613 . 111.37(9) yes
C607 . B600 . C613 . 104.20(9) yes
C601 . B600 . C619 . 104.18(9) yes
C607 . B600 . C619 . 113.32(9) yes
C613 . B600 . C619 . 112.62(9) yes
B600 . C601 . C602 . 123.61(11) yes
B600 . C601 . C606 . 120.97(10) yes
C602 . C601 . C606 . 115.27(11) yes
C601 . C602 . C603 . 122.56(14) yes
C601 . C602 . H6021 . 118.8 no
C603 . C602 . H6021 . 118.6 no
C602 . C603 . C604 . 120.25(14) yes
C602 . C603 . H6031 . 119.6 no
C604 . C603 . H6031 . 120.1 no
C603 . C604 . C605 . 119.08(13) yes
C603 . C604 . H6041 . 118.8 no
C605 . C604 . H6041 . 122.1 no
C604 . C605 . C606 . 120.19(14) yes
C604 . C605 . H6051 . 120.4 no
C606 . C605 . H6051 . 119.4 no
C601 . C606 . C605 . 122.59(13) yes
C601 . C606 . H6061 . 118.1 no
C605 . C606 . H6061 . 119.3 no
B600 . C607 . C608 . 122.84(10) yes
B600 . C607 . C612 . 121.80(10) yes
C608 . C607 . C612 . 115.02(11) yes
C607 . C608 . C609 . 123.08(12) yes
C607 . C608 . H6081 . 118.6 no
C609 . C608 . H6081 . 118.3 no
C608 . C609 . C610 . 120.18(12) yes
C608 . C609 . H6091 . 119.9 no
C610 . C609 . H6091 . 119.9 no
C609 . C610 . C611 . 118.94(12) yes
C609 . C610 . H6101 . 120.2 no
C611 . C610 . H6101 . 120.8 no
C610 . C611 . C612 . 120.08(12) yes
C610 . C611 . H6111 . 120.4 no
C612 . C611 . H6111 . 119.5 no
C607 . C612 . C611 . 122.68(12) yes
C607 . C612 . H6121 . 119.1 no
C611 . C612 . H6121 . 118.2 no
B600 . C613 . C614 . 125.52(11) yes
B600 . C613 . C618 . 119.43(10) yes
C614 . C613 . C618 . 114.91(11) yes
C613 . C614 . C615 . 122.60(13) yes
C613 . C614 . H6141 . 118.9 no
C615 . C614 . H6141 . 118.5 no
C614 . C615 . C616 . 120.25(13) yes
C614 . C615 . H6151 . 118.8 no
C616 . C615 . H6151 . 121.0 no
C615 . C616 . C617 . 119.30(13) yes
C615 . C616 . H6161 . 121.1 no
C617 . C616 . H6161 . 119.5 no
C616 . C617 . C618 . 119.70(14) yes
C616 . C617 . H6171 . 120.0 no
C618 . C617 . H6171 . 120.3 no
C613 . C618 . C617 . 123.22(13) yes
C613 . C618 . H6181 . 117.8 no
C617 . C618 . H6181 . 119.0 no
B600 . C619 . C620 . 124.52(11) yes
B600 . C619 . C624 . 120.05(10) yes
C620 . C619 . C624 . 115.15(11) yes
C619 . C620 . C621 . 122.36(13) yes
C619 . C620 . H6201 . 118.8 no
C621 . C620 . H6201 . 118.8 no
C620 . C621 . C622 . 120.51(14) yes
C620 . C621 . H6211 . 118.4 no
C622 . C621 . H6211 . 121.1 no
C621 . C622 . C623 . 118.95(13) yes
C621 . C622 . H6221 . 121.7 no
C623 . C622 . H6221 . 119.4 no
C622 . C623 . C624 . 120.00(13) yes
C622 . C623 . H6231 . 119.5 no
C624 . C623 . H6231 . 120.5 no
C619 . C624 . C623 . 122.92(13) yes
C619 . C624 . H6241 . 119.0 no
C623 . C624 . H6241 . 118.1 no
C24 . O25 . H251 . 121.6 no
C22 . C23 . C24 . 105.2(15) yes
C22 . C23 . H232 . 111.4 no
C24 . C23 . H232 . 107.4 no
C22 . C23 . H231 . 111.1 no
C24 . C23 . H231 . 109.6 no
H232 . C23 . H231 . 111.9 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H241 . C22 . 121 1.14 2.56 3.289(7) yes
C6 . H241 . C2 . 121 1.14 2.28 3.024(7) yes
C8 . H293 . C6 . 132 0.81 1.81 2.434(7) yes
C28 . H281 . C605 3_546 170 0.98 2.55 3.520(7) yes
C9 . H281 . C605 3_546 129 1.11 2.55 3.366(7) yes
C30 . H303 . O5 . 126 0.97 2.39 3.059(7) yes
C10 . H303 . O5 . 126 0.74 2.39 2.894(7) yes
C30 . H303 . O25 . 123 0.97 2.36 2.992(7) yes
C10 . H303 . O25 . 123 0.74 2.36 2.827(7) 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_MB7_100_A3_180202_EphBr_Mo
_database_code_depnum_ccdc_archive 'CCDC 1823200'
_audit_update_record             
;
2018-02-09 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 Br N O'
_chemical_formula_weight         246.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4467(2)
_cell_length_b                   6.20961(16)
_cell_length_c                   12.5863(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.176(3)
_cell_angle_gamma                90
_cell_volume                     570.96(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    5008
_cell_measurement_theta_min      3.296
_cell_measurement_theta_max      31.387

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.565
_shelx_estimated_absorpt_T_min   0.323
_shelx_estimated_absorpt_T_max   0.842
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Agilent SuperNova dual radiation CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_reflns_number            9436
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.952
_diffrn_reflns_theta_max         32.888
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3804
_reflns_number_gt                3388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_max     0.852
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Rigaku, 2015)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku, 2015)'
_computing_data_reduction        'CrysAlis PRO (Rigaku, 2015)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.0346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1363 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(5)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3804
_refine_ls_number_parameters     121
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0749
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6376(4) 0.5680(5) 0.2364(3) 0.0247(7) Uani 1 1 d . . . . .
H1 H 0.5163 0.6427 0.2231 0.030 Uiso 1 1 calc R U . . .
C2 C 0.7788(4) 0.7162(5) 0.1991(3) 0.0225(6) Uani 1 1 d . . . . .
H2 H 0.8049 0.8397 0.2508 0.027 Uiso 1 1 calc R U . . .
C3 C 0.9582(4) 0.6031(5) 0.1945(3) 0.0278(6) Uani 1 1 d . . . . .
H3A H 0.9369 0.4916 0.1383 0.042 Uiso 1 1 calc R U . . .
H3B H 1.0068 0.5365 0.2648 0.042 Uiso 1 1 calc R U . . .
H3C H 1.0466 0.7082 0.1773 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7944(5) 0.9827(5) 0.0495(3) 0.0319(8) Uani 1 1 d . . . . .
H4A H 0.9177 0.9345 0.0442 0.048 Uiso 1 1 calc R U . . .
H4B H 0.8033 1.1039 0.1002 0.048 Uiso 1 1 calc R U . . .
H4C H 0.7287 1.0286 -0.0220 0.048 Uiso 1 1 calc R U . . .
C5 C 0.6922(3) 0.5198(11) 0.3558(2) 0.0236(5) Uani 1 1 d . . . . .
C6 C 0.7848(5) 0.3321(5) 0.3951(3) 0.0303(7) Uani 1 1 d . . . . .
H6 H 0.8148 0.2290 0.3456 0.036 Uiso 1 1 calc R U . . .
C7 C 0.8327(5) 0.2946(6) 0.5038(3) 0.0374(8) Uani 1 1 d . . . . .
H7 H 0.8940 0.1649 0.5291 0.045 Uiso 1 1 calc R U . . .
C8 C 0.7923(6) 0.4455(7) 0.5780(3) 0.0399(9) Uani 1 1 d . . . . .
H8 H 0.8280 0.4197 0.6535 0.048 Uiso 1 1 calc R U . . .
C9 C 0.7013(6) 0.6307(7) 0.5416(3) 0.0392(9) Uani 1 1 d . . . . .
H9 H 0.6727 0.7332 0.5919 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6501(5) 0.6692(6) 0.4300(3) 0.0313(7) Uani 1 1 d . . . . .
H10 H 0.5865 0.7977 0.4048 0.038 Uiso 1 1 calc R U . . .
N1 N 0.6938(4) 0.8026(4) 0.0893(2) 0.0241(5) Uani 1 1 d . . . . .
H1A H 0.6840 0.6929 0.0406 0.029 Uiso 1 1 calc R U . . .
H1B H 0.5784 0.8483 0.0914 0.029 Uiso 1 1 calc R U . . .
O1 O 0.6251(4) 0.3848(4) 0.1681(2) 0.0352(6) Uani 1 1 d . . . . .
H1C H 0.5368 0.3077 0.1775 0.053 Uiso 1 1 calc R U . . .
Br1 Br 0.31137(4) 0.02448(7) 0.13253(2) 0.02967(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.418(4) . ?
C1 C5 1.509(4) . ?
C1 C2 1.538(4) . ?
C1 H1 1.0000 . ?
C2 N1 1.504(4) . ?
C2 C3 1.521(4) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N1 1.486(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.394(6) . ?
C5 C6 1.395(7) . ?
C6 C7 1.365(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.368(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
O1 H1C 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C5 114.7(3) . . ?
O1 C1 C2 105.3(2) . . ?
C5 C1 C2 110.7(3) . . ?
O1 C1 H1 108.6 . . ?
C5 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
N1 C2 C3 110.2(2) . . ?
N1 C2 C1 107.6(2) . . ?
C3 C2 C1 113.2(3) . . ?
N1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 118.6(3) . . ?
C10 C5 C1 118.8(5) . . ?
C6 C5 C1 122.5(4) . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.8(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.0(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 120.3(4) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C4 N1 C2 115.4(3) . . ?
C4 N1 H1A 108.4 . . ?
C2 N1 H1A 108.4 . . ?
C4 N1 H1B 108.4 . . ?
C2 N1 H1B 108.4 . . ?
H1A N1 H1B 107.5 . . ?
C1 O1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 69.8(3) . . . . ?
C5 C1 C2 N1 -165.7(3) . . . . ?
O1 C1 C2 C3 -52.2(4) . . . . ?
C5 C1 C2 C3 72.3(4) . . . . ?
O1 C1 C5 C10 -158.7(3) . . . . ?
C2 C1 C5 C10 82.4(3) . . . . ?
O1 C1 C5 C6 21.9(4) . . . . ?
C2 C1 C5 C6 -97.1(4) . . . . ?
C10 C5 C6 C7 0.2(5) . . . . ?
C1 C5 C6 C7 179.7(3) . . . . ?
C5 C6 C7 C8 -1.0(6) . . . . ?
C6 C7 C8 C9 1.1(6) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
C6 C5 C10 C9 0.4(5) . . . . ?
C1 C5 C10 C9 -179.1(3) . . . . ?
C8 C9 C10 C5 -0.2(6) . . . . ?
C3 C2 N1 C4 -68.0(3) . . . . ?
C1 C2 N1 C4 168.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br1 0.91 2.42 3.277(3) 156.3 2_655
N1 H1B Br1 0.91 2.41 3.302(3) 165.9 1_565
O1 H1C Br1 0.84 2.42 3.203(2) 155.2 .

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.074



####################################################################### 
# 
# 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_I_CCDC11
_database_code_depnum_ccdc_archive 'CCDC 1585751'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   9.00810(10)
_cell_length_b                   9.32180(10)
_cell_length_c                   19.4957(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.3510(9)
_cell_angle_gamma                90
_cell_volume                     1629.95(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_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'


_cell_formula_units_Z            2

# Given Formula = C36 H36 N4 O8 
# Dc =      1.33 Fooo =    688.00 Mu =      7.83 M =    652.70
# Found Formula = C36 H38.00 N4 O8 
# Dc =      1.33 FOOO =    692.00 Mu =      7.83 M =    654.72

_chemical_formula_sum            'C36 H38 N4 O8'
_chemical_formula_moiety         '2(C17 H19 N2 O), C2 O4, 2(O)'
_chemical_compound_source        ?
_chemical_formula_weight         654.72


_cell_measurement_reflns_used    21280
_cell_measurement_theta_min      5
_cell_measurement_theta_max      79
_cell_measurement_temperature    160

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_max          0.106

_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             691.996
_exptl_absorpt_coefficient_mu    0.783

# Sheldrick geometric approximatio 0.92 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.98
_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    'SIR92 (Altomare et al., 1994)'
_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      160
_diffrn_reflns_number            34550
_reflns_number_total             6622
_diffrn_reflns_av_R_equivalents  0.031
# Number of reflections without Friedels Law is 6622 
# Number of reflections with Friedels Law is 3544 
# Theoretical number of reflections is about 3333 


_diffrn_reflns_theta_min         4.556
_diffrn_reflns_theta_max         74.493
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        74.493
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   2.25
_oxford_diffrn_Wilson_scale      0.11

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

_refine_diff_density_min         -0.24
_refine_diff_density_max         0.31


# 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         6622
_refine_ls_number_restraints     67
_refine_ls_number_parameters     516
_oxford_refine_ls_R_factor_ref   0.0356
_refine_ls_wR_factor_ref         0.0984
_refine_ls_goodness_of_fit_ref   0.9838
_refine_ls_shift/su_max          0.0055179
_refine_ls_shift/su_mean         0.0004151


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6622
_refine_ls_R_factor_all          0.0356
_refine_ls_wR_factor_all         0.0984

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6365
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_gt          0.0973

_refine_ls_abs_structure_Flack   0.17(14)
_refine_ls_abs_structure_details 'Flack (1983), 3078 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) + ( 0.06P)² + 0.43P] 
 ,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 -0.32343(16) 0.3385(2) 0.60159(8) 0.0341 1.0000 Uani . . . . . .
C2 C -0.32627(19) 0.2499(2) 0.66476(9) 0.0322 1.0000 Uani . . . . . .
C3 C -0.19053(18) 0.1490(2) 0.67420(9) 0.0258 1.0000 Uani . . . . . .
C4 C -0.04690(17) 0.23005(19) 0.67948(8) 0.0222 1.0000 Uani . . . . . .
C5 C 0.04607(17) 0.2501(2) 0.62889(8) 0.0241 1.0000 Uani . . . . . .
N6 N 0.16188(16) 0.33923(18) 0.65150(7) 0.0248 1.0000 Uani . . . . . .
C7 C 0.14416(17) 0.3798(2) 0.71837(8) 0.0223 1.0000 Uani . . . . . .
C8 C 0.01460(17) 0.3116(2) 0.73792(8) 0.0206 1.0000 Uani . . . . . .
C9 C 0.22964(18) 0.4703(2) 0.76320(9) 0.0270 1.0000 Uani . . . . . .
C10 C 0.18530(19) 0.4891(2) 0.82831(9) 0.0275 1.0000 Uani . . . . . .
C11 C 0.05911(18) 0.41778(19) 0.84976(8) 0.0231 1.0000 Uani . . . . . .
C12 C -0.02846(16) 0.3303(2) 0.80515(8) 0.0215 1.0000 Uani . . . . . .
O13 O 0.03361(14) 0.44284(17) 0.91722(6) 0.0289 1.0000 Uani . . . . . .
C14 C -0.07420(17) 0.3519(2) 0.94552(8) 0.0239 1.0000 Uani . . . . . .
C15 C -0.08089(17) 0.3932(2) 1.01974(8) 0.0236 1.0000 Uani . . . . . .
C16 C -0.16646(19) 0.5110(2) 1.03694(9) 0.0277 1.0000 Uani . . . . . .
C17 C -0.1697(2) 0.5510(2) 1.10548(10) 0.0336 1.0000 Uani . . . . . .
C18 C -0.0899(2) 0.4731(3) 1.15699(10) 0.0367 1.0000 Uani . . . . . .
C19 C -0.0093(2) 0.3542(3) 1.14061(10) 0.0369 1.0000 Uani . . . . . .
C20 C -0.0041(2) 0.3144(2) 1.07193(9) 0.0308 1.0000 Uani . . . . . .
N21 N 0.16049(18) 0.88099(19) 0.57327(8) 0.0284 0.8828(14) Uani . U P 1 1 .
C22 C 0.1679(2) 0.8979(2) 0.65055(10) 0.0342 1.0000 Uani D . . . . .
C23 C 0.31070(18) 0.9719(2) 0.67756(9) 0.0262 1.0000 Uani . . . . . .
C24 C 0.44748(17) 0.87925(19) 0.67981(8) 0.0227 1.0000 Uani . . . . . .
C25 C 0.53892(19) 0.8552(2) 0.62813(9) 0.0274 1.0000 Uani . . . . . .
N26 N 0.64869(16) 0.7601(2) 0.64982(8) 0.0304 1.0000 Uani . . . . . .
C27 C 0.63075(18) 0.7202(2) 0.71656(9) 0.0251 1.0000 Uani . . . . . .
C28 C 0.50586(17) 0.79346(19) 0.73736(8) 0.0210 1.0000 Uani . . . . . .
C29 C 0.71424(18) 0.6269(2) 0.76136(9) 0.0296 1.0000 Uani . . . . . .
C30 C 0.67250(19) 0.6119(2) 0.82710(8) 0.0281 1.0000 Uani . . . . . .
C31 C 0.54977(18) 0.68791(19) 0.84922(8) 0.0233 1.0000 Uani . . . . . .
C32 C 0.46520(17) 0.77809(19) 0.80507(8) 0.0214 1.0000 Uani . . . . . .
O33 O 0.52581(14) 0.66322(17) 0.91697(6) 0.0296 1.0000 Uani . . . . . .
C34 C 0.42126(18) 0.7565(2) 0.94624(8) 0.0244 1.0000 Uani . . . . . .
C35 C 0.41460(17) 0.7117(2) 1.02003(8) 0.0233 1.0000 Uani . . . . . .
C36 C 0.4913(2) 0.7884(2) 1.07309(9) 0.0297 1.0000 Uani . . . . . .
C37 C 0.4858(2) 0.7462(3) 1.14129(10) 0.0363 1.0000 Uani . . . . . .
C38 C 0.4043(2) 0.6263(2) 1.15632(9) 0.0327 1.0000 Uani . . . . . .
C39 C 0.3261(2) 0.5507(2) 1.10374(10) 0.0323 1.0000 Uani . . . . . .
C40 C 0.33007(18) 0.5941(2) 1.03605(9) 0.0274 1.0000 Uani . . . . . .
O41 O 0.39560(17) 0.63325(19) 0.50109(8) 0.0390 0.8828(14) Uani . U P 1 1 .
C42 C 0.3364(2) 0.5289(2) 0.52846(9) 0.0238 0.8828(14) Uani . . P 1 1 .
O43 O 0.39729(14) 0.44623(18) 0.57295(7) 0.0302 0.8828(14) Uani . . P 1 1 .
C44 C 0.1711(3) 0.4985(3) 0.50473(13) 0.0245 0.8828(14) Uani . U P 1 1 .
O45 O 0.08199(15) 0.59855(18) 0.51529(8) 0.0339 0.8828(14) Uani . . P 1 1 .
O46 O 0.14065(15) 0.38059(18) 0.47767(8) 0.0313 0.8828(14) Uani . . P 1 1 .
O47 O 0.09788(15) 1.07117(18) 0.37856(8) 0.0330 0.8828(14) Uani . . P 1 1 .
O48 O 0.29951(18) 1.1164(2) 0.51036(9) 0.0360 0.8828(14) Uani . . P 1 1 .
N121 N 0.1771(13) 0.7709(9) 0.6029(5) 0.0282 0.1172(14) Uani D U P 1 2 .
O141 O 0.3620(12) 1.2306(12) 0.5206(6) 0.0391 0.1172(14) Uani D U P 1 2 .
C142 C 0.3324(14) 1.1117(15) 0.4946(9) 0.0245 0.1172(14) Uani D U P 1 2 .
O143 O 0.4174(12) 1.0153(12) 0.4833(6) 0.0392 0.1172(14) Uani D U P 1 2 .
C144 C 0.1667(12) 1.0825(13) 0.4711(6) 0.0246 0.1172(14) Uani D U P 1 2 .
O145 O 0.1014(12) 1.1649(13) 0.4256(6) 0.0388 0.1172(14) Uani D U P 1 2 .
O146 O 0.1055(13) 0.9788(13) 0.4993(6) 0.0394 0.1172(14) Uani D U P 1 2 .
O148 O 0.203(2) 0.503(2) 0.4935(10) 0.0393 0.1172(14) Uani . U P 1 2 .
O147 O 0.4018(13) 0.5374(13) 0.6211(6) 0.0391 0.1172(14) Uani . U P 1 2 .
H161 H -0.2210 0.5617 1.0018 0.0331 1.0000 Uiso R . . . . .
H171 H -0.2264 0.6342 1.1164 0.0399 1.0000 Uiso R . . . . .
H181 H -0.0889 0.5028 1.2041 0.0435 1.0000 Uiso R . . . . .
H191 H 0.0480 0.3026 1.1764 0.0452 1.0000 Uiso R . . . . .
H201 H 0.0543 0.2372 1.0612 0.0379 1.0000 Uiso R . . . . .
H142 H -0.0413 0.2529 0.9406 0.0299 1.0000 Uiso R . . . . .
H141 H -0.1708 0.3665 0.9199 0.0286 1.0000 Uiso R . . . . .
H13 H -0.3298 0.2589 0.5658 0.0426 1.0000 Uiso R . . . . .
H12 H -0.2413 0.4038 0.6026 0.0514 1.0000 Uiso R . . . . .
H11 H -0.4101 0.3931 0.5918 0.0507 1.0000 Uiso R . . . . .
H21 H -0.3296 0.3152 0.7053 0.0401 1.0000 Uiso R . . . . .
H22 H -0.4140 0.1932 0.6599 0.0381 1.0000 Uiso R . . . . .
H31 H -0.1971 0.0923 0.7166 0.0296 1.0000 Uiso R . . . . .
H32 H -0.1932 0.0845 0.6336 0.0306 1.0000 Uiso R . . . . .
H51 H 0.0369 0.2088 0.5853 0.0288 1.0000 Uiso R . . . . .
H61 H 0.2293 0.3683 0.6281 0.0315 1.0000 Uiso R . . . . .
H101 H 0.2425 0.5471 0.8605 0.0323 1.0000 Uiso R . . . . .
H91 H 0.3172 0.5160 0.7508 0.0321 1.0000 Uiso R . . . . .
H121 H -0.1104 0.2837 0.8183 0.0260 1.0000 Uiso R . . . . .
H301 H 0.7275 0.5455 0.8590 0.0340 1.0000 Uiso R . . . . .
H291 H 0.7977 0.5755 0.7467 0.0354 1.0000 Uiso R . . . . .
H261 H 0.7207 0.7285 0.6246 0.0373 1.0000 Uiso R . . . . .
H251 H 0.5353 0.8912 0.5812 0.0328 1.0000 Uiso R . . . . .
H231 H 0.2948 1.0026 0.7249 0.0303 1.0000 Uiso R . . . . .
H232 H 0.3239 1.0596 0.6492 0.0306 1.0000 Uiso R . . . . .
H321 H 0.3821 0.8328 0.8196 0.0255 1.0000 Uiso R . . . . .
H361 H 0.5442 0.8733 1.0631 0.0362 1.0000 Uiso R . . . . .
H371 H 0.5377 0.8001 1.1776 0.0438 1.0000 Uiso R . . . . .
H381 H 0.4028 0.5955 1.2020 0.0388 1.0000 Uiso R . . . . .
H391 H 0.2720 0.4689 1.1144 0.0398 1.0000 Uiso R . . . . .
H401 H 0.2750 0.5426 0.9993 0.0333 1.0000 Uiso R . . . . .
H342 H 0.4556 0.8578 0.9442 0.0278 1.0000 Uiso R . . . . .
H341 H 0.3200 0.7463 0.9190 0.0296 1.0000 Uiso R . . . . .
H224 H 0.0809 0.9544 0.6610 0.0396 0.8828(14) Uiso R . P 1 1 .
H223 H 0.1609 0.8084 0.6731 0.0374 0.8828(14) Uiso R . P 1 1 .
H222 H 0.1239 0.8602 0.6905 0.0409 0.1172(14) Uiso R . P 1 2 .
H221 H 0.1009 0.9689 0.6277 0.0411 0.1172(14) Uiso R . P 1 2 .
H1212 H 0.1044 0.7087 0.6098 0.0460 0.1172(14) Uiso R . P 1 2 .
H1213 H 0.2655 0.7278 0.6115 0.0458 0.1172(14) Uiso R . P 1 2 .
H1211 H 0.1664 0.8003 0.5592 0.0459 0.1172(14) Uiso R . P 1 2 .
H211 H 0.0630 0.8688 0.5578 0.0436 0.8828(14) Uiso R . P 1 1 .
H212 H 0.1973 0.9585 0.5526 0.0438 0.8828(14) Uiso R . P 1 1 .
H213 H 0.2131 0.8053 0.5619 0.0426 0.8828(14) Uiso R . P 1 1 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.04(3)
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 . 1.485(2) yes
N1 . H13 . 1.016 no
N1 . H12 . 0.957 no
N1 . H11 . 0.936 no
C2 . C3 . 1.540(2) yes
C2 . H21 . 1.001 no
C2 . H22 . 0.948 no
C3 . C4 . 1.494(2) yes
C3 . H31 . 0.988 no
C3 . H32 . 0.993 no
C4 . C5 . 1.365(2) yes
C4 . C8 . 1.437(2) yes
C5 . N6 . 1.374(2) yes
C5 . H51 . 0.929 no
N6 . C7 . 1.381(2) yes
N6 . H61 . 0.838 no
C7 . C8 . 1.412(2) yes
C7 . C9 . 1.394(2) yes
C8 . C12 . 1.412(2) yes
C9 . C10 . 1.377(2) yes
C9 . H91 . 0.947 no
C10 . C11 . 1.413(2) yes
C10 . H101 . 0.944 no
C11 . C12 . 1.384(2) yes
C11 . O13 . 1.376(2) yes
C12 . H121 . 0.913 no
O13 . C14 . 1.4371(19) yes
C14 . C15 . 1.504(2) yes
C14 . H142 . 0.977 no
C14 . H141 . 0.972 no
C15 . C16 . 1.400(2) yes
C15 . C20 . 1.386(2) yes
C16 . C17 . 1.390(3) yes
C16 . H161 . 0.934 no
C17 . C18 . 1.385(3) yes
C17 . H171 . 0.963 no
C18 . C19 . 1.378(3) yes
C18 . H181 . 0.958 no
C19 . C20 . 1.394(3) yes
C19 . H191 . 0.958 no
C20 . H201 . 0.927 no
N21 . C22 . 1.510(2) yes
N21 . H211 . 0.909 no
N21 . H212 . 0.905 no
N21 . H213 . 0.889 no
C22 . C23 . 1.511(2) yes
C22 . H224 . 0.981 no
C22 . H223 . 0.948 no
C22 . C23 . 1.511(2) yes
C22 . N121 . 1.512(5) yes
C22 . H222 . 0.972 no
C22 . H221 . 0.976 no
C23 . C24 . 1.502(2) yes
C23 . H231 . 0.989 no
C23 . H232 . 1.000 no
C24 . C25 . 1.378(2) yes
C24 . C28 . 1.437(2) yes
C25 . N26 . 1.365(2) yes
C25 . H251 . 0.973 no
N26 . C27 . 1.377(2) yes
N26 . H261 . 0.899 no
C27 . C28 . 1.408(2) yes
C27 . C29 . 1.401(2) yes
C28 . C32 . 1.410(2) yes
C29 . C30 . 1.376(2) yes
C29 . H291 . 0.957 no
C30 . C31 . 1.414(2) yes
C30 . H301 . 0.978 no
C31 . C32 . 1.381(2) yes
C31 . O33 . 1.377(2) yes
C32 . H321 . 0.969 no
O33 . C34 . 1.4386(19) yes
C34 . C35 . 1.505(2) yes
C34 . H342 . 0.995 no
C34 . H341 . 1.016 no
C35 . C36 . 1.387(2) yes
C35 . C40 . 1.387(2) yes
C36 . C37 . 1.392(3) yes
C36 . H361 . 0.954 no
C37 . C38 . 1.383(3) yes
C37 . H371 . 0.954 no
C38 . C39 . 1.382(3) yes
C38 . H381 . 0.936 no
C39 . C40 . 1.384(3) yes
C39 . H391 . 0.939 no
C40 . H401 . 0.962 no
O41 . C42 . 1.252(2) yes
C42 . O43 . 1.248(2) yes
C42 . C44 . 1.544(3) yes
C44 . O45 . 1.260(3) yes
C44 . O46 . 1.238(3) yes
N121 . H1212 . 0.894 no
N121 . H1213 . 0.894 no
N121 . H1211 . 0.890 no
O141 . C142 . 1.237(14) yes
C142 . O143 . 1.214(14) yes
C142 . C144 . 1.545(13) yes
C144 . O145 . 1.276(12) yes
C144 . O146 . 1.263(13) 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 . H13 . 99.1 no
C2 . N1 . H12 . 114.2 no
H13 . N1 . H12 . 118.2 no
C2 . N1 . H11 . 113.1 no
H13 . N1 . H11 . 105.4 no
H12 . N1 . H11 . 106.7 no
N1 . C2 . C3 . 111.34(14) yes
N1 . C2 . H21 . 108.7 no
C3 . C2 . H21 . 111.0 no
N1 . C2 . H22 . 107.9 no
C3 . C2 . H22 . 108.4 no
H21 . C2 . H22 . 109.3 no
C2 . C3 . C4 . 111.86(14) yes
C2 . C3 . H31 . 108.5 no
C4 . C3 . H31 . 109.4 no
C2 . C3 . H32 . 108.3 no
C4 . C3 . H32 . 108.5 no
H31 . C3 . H32 . 110.2 no
C3 . C4 . C5 . 127.26(15) yes
C3 . C4 . C8 . 126.13(14) yes
C5 . C4 . C8 . 106.47(14) yes
C4 . C5 . N6 . 110.47(15) yes
C4 . C5 . H51 . 126.6 no
N6 . C5 . H51 . 122.9 no
C5 . N6 . C7 . 108.50(13) yes
C5 . N6 . H61 . 126.0 no
C7 . N6 . H61 . 125.4 no
N6 . C7 . C8 . 107.63(14) yes
N6 . C7 . C9 . 130.68(15) yes
C8 . C7 . C9 . 121.70(14) yes
C4 . C8 . C7 . 106.93(13) yes
C4 . C8 . C12 . 133.04(14) yes
C7 . C8 . C12 . 120.02(14) yes
C7 . C9 . C10 . 117.64(15) yes
C7 . C9 . H91 . 122.4 no
C10 . C9 . H91 . 119.9 no
C9 . C10 . C11 . 121.57(15) yes
C9 . C10 . H101 . 119.8 no
C11 . C10 . H101 . 118.5 no
C10 . C11 . C12 . 121.21(15) yes
C10 . C11 . O13 . 114.43(14) yes
C12 . C11 . O13 . 124.36(14) yes
C8 . C12 . C11 . 117.79(14) yes
C8 . C12 . H121 . 120.0 no
C11 . C12 . H121 . 122.2 no
C11 . O13 . C14 . 116.48(12) yes
O13 . C14 . C15 . 107.92(13) yes
O13 . C14 . H142 . 107.3 no
C15 . C14 . H142 . 112.1 no
O13 . C14 . H141 . 108.9 no
C15 . C14 . H141 . 110.2 no
H142 . C14 . H141 . 110.2 no
C14 . C15 . C16 . 120.23(15) yes
C14 . C15 . C20 . 120.57(15) yes
C16 . C15 . C20 . 119.19(16) yes
C15 . C16 . C17 . 120.13(17) yes
C15 . C16 . H161 . 119.0 no
C17 . C16 . H161 . 120.9 no
C16 . C17 . C18 . 120.02(18) yes
C16 . C17 . H171 . 119.2 no
C18 . C17 . H171 . 120.8 no
C17 . C18 . C19 . 120.17(18) yes
C17 . C18 . H181 . 120.1 no
C19 . C18 . H181 . 119.7 no
C18 . C19 . C20 . 120.11(18) yes
C18 . C19 . H191 . 119.7 no
C20 . C19 . H191 . 120.1 no
C19 . C20 . C15 . 120.32(18) yes
C19 . C20 . H201 . 119.6 no
C15 . C20 . H201 . 120.0 no
C22 . N21 . H211 . 107.2 no
C22 . N21 . H212 . 112.2 no
H211 . N21 . H212 . 109.6 no
C22 . N21 . H213 . 110.8 no
H211 . N21 . H213 . 109.8 no
H212 . N21 . H213 . 107.2 no
N21 . C22 . C23 . 110.62(15) yes
N21 . C22 . H224 . 107.5 no
C23 . C22 . H224 . 110.7 no
N21 . C22 . H223 . 111.8 no
C23 . C22 . H223 . 109.4 no
H224 . C22 . H223 . 106.7 no
C23 . C22 . N121 . 118.6(5) yes
C23 . C22 . H222 . 106.5 no
N121 . C22 . H222 . 105.0 no
C23 . C22 . H221 . 108.6 no
N121 . C22 . H221 . 108.5 no
H222 . C22 . H221 . 109.3 no
C22 . C23 . C24 . 114.67(15) yes
C22 . C23 . H231 . 105.3 no
C24 . C23 . H231 . 109.2 no
C22 . C23 . H232 . 108.8 no
C24 . C23 . H232 . 110.3 no
H231 . C23 . H232 . 108.3 no
C23 . C24 . C25 . 128.09(15) yes
C23 . C24 . C28 . 125.62(15) yes
C25 . C24 . C28 . 106.27(14) yes
C24 . C25 . N26 . 110.13(15) yes
C24 . C25 . H251 . 131.5 no
N26 . C25 . H251 . 118.4 no
C25 . N26 . C27 . 108.83(14) yes
C25 . N26 . H261 . 125.6 no
C27 . N26 . H261 . 125.6 no
N26 . C27 . C28 . 107.96(14) yes
N26 . C27 . C29 . 130.79(15) yes
C28 . C27 . C29 . 121.24(15) yes
C24 . C28 . C27 . 106.81(14) yes
C24 . C28 . C32 . 132.81(15) yes
C27 . C28 . C32 . 120.32(14) yes
C27 . C29 . C30 . 117.79(15) yes
C27 . C29 . H291 . 121.0 no
C30 . C29 . H291 . 121.2 no
C29 . C30 . C31 . 121.50(15) yes
C29 . C30 . H301 . 119.3 no
C31 . C30 . H301 . 119.2 no
C30 . C31 . C32 . 121.11(15) yes
C30 . C31 . O33 . 113.93(14) yes
C32 . C31 . O33 . 124.96(14) yes
C28 . C32 . C31 . 117.99(14) yes
C28 . C32 . H321 . 119.7 no
C31 . C32 . H321 . 122.3 no
C31 . O33 . C34 . 116.50(12) yes
O33 . C34 . C35 . 107.30(13) yes
O33 . C34 . H342 . 109.9 no
C35 . C34 . H342 . 109.9 no
O33 . C34 . H341 . 109.0 no
C35 . C34 . H341 . 111.0 no
H342 . C34 . H341 . 109.6 no
C34 . C35 . C36 . 120.55(15) yes
C34 . C35 . C40 . 120.43(15) yes
C36 . C35 . C40 . 119.02(16) yes
C35 . C36 . C37 . 120.44(17) yes
C35 . C36 . H361 . 119.9 no
C37 . C36 . H361 . 119.6 no
C36 . C37 . C38 . 119.85(17) yes
C36 . C37 . H371 . 120.1 no
C38 . C37 . H371 . 120.1 no
C37 . C38 . C39 . 119.92(17) yes
C37 . C38 . H381 . 120.3 no
C39 . C38 . H381 . 119.8 no
C38 . C39 . C40 . 120.12(17) yes
C38 . C39 . H391 . 119.3 no
C40 . C39 . H391 . 120.6 no
C35 . C40 . C39 . 120.61(16) yes
C35 . C40 . H401 . 118.9 no
C39 . C40 . H401 . 120.5 no
O41 . C42 . O43 . 126.79(17) yes
O41 . C42 . C44 . 116.88(17) yes
O43 . C42 . C44 . 116.33(17) yes
C42 . C44 . O45 . 115.2(2) yes
C42 . C44 . O46 . 117.36(19) yes
O45 . C44 . O46 . 127.4(2) yes
C22 . N121 . H1212 . 109.3 no
C22 . N121 . H1213 . 109.5 no
H1212 . N121 . H1213 . 109.4 no
C22 . N121 . H1211 . 109.8 no
H1212 . N121 . H1211 . 109.2 no
H1213 . N121 . H1211 . 109.5 no
O141 . C142 . O143 . 128.5(11) yes
O141 . C142 . C144 . 116.4(10) yes
O143 . C142 . C144 . 115.1(10) yes
C142 . C144 . O145 . 118.1(9) yes
C142 . C144 . O146 . 117.1(10) yes
O145 . C144 . O146 . 124.9(9) 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
N1 . H13 . O41 2_546 164 1.02 1.81 2.801(3) yes
N1 . H12 . O47 2_546 165 0.96 2.04 2.972(3) yes
N1 . H12 . C144 2_546 135 0.96 2.34 3.090(3) yes
N1 . H12 . O146 2_546 126 0.96 2.53 3.186(3) yes
N1 . H11 . O43 1_455 163 0.94 1.81 2.718(3) yes
N1 . H11 . O147 1_455 154 0.94 2.28 3.144(3) yes
C3 . H32 . O148 2_546 160 0.99 2.59 3.534(3) yes
C5 . H51 . O45 2_546 158 0.93 2.38 3.259(3) yes
N6 . H61 . O43 . 178 0.84 2.07 2.906(3) yes
N6 . H61 . O147 . 144 0.84 2.23 2.945(3) yes
N26 . H261 . O47 2_646 144 0.90 2.20 2.976(3) yes
N26 . H261 . C142 2_646 123 0.90 2.57 3.156(3) yes
N26 . H261 . C144 2_646 156 0.90 2.59 3.434(3) yes
N26 . H261 . O145 2_646 175 0.90 2.04 2.938(3) yes
C25 . H251 . O143 . 153 0.97 2.39 3.290(3) yes
N121 . H1212 . O47 2_546 173 0.89 2.26 3.146(3) yes
N121 . H1212 . O145 2_546 140 0.89 1.96 2.705(3) yes
N121 . H1213 . O147 . 151 0.89 2.16 2.971(3) yes
N21 . H1211 . O45 . 156 0.80 2.17 2.926(3) yes
N121 . H1211 . O146 . 142 0.89 2.08 2.830(3) yes
N21 . H211 . O46 2_556 169 0.91 1.90 2.800(3) yes
N21 . H211 . O145 2_546 129 0.91 2.45 3.103(3) yes
N21 . H212 . O48 . 173 0.91 1.96 2.859(3) yes
N21 . H212 . C142 . 166 0.91 2.25 3.134(3) yes
N21 . H212 . O143 . 137 0.91 2.56 3.280(3) yes
N21 . H212 . C144 . 143 0.91 1.96 2.742(3) yes
N121 . H213 . O146 . 123 0.95 2.20 2.830(3) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_PN220716_10444_A3_D3_Mo
_database_code_depnum_ccdc_archive 'CCDC 1585764'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 Cl I N5 O'
_chemical_formula_weight         499.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.9279(2)
_cell_length_b                   12.54570(15)
_cell_length_c                   13.13900(15)
_cell_angle_alpha                90
_cell_angle_beta                 109.8430(12)
_cell_angle_gamma                90
_cell_volume                     2004.48(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    9061
_cell_measurement_theta_min      3.631
_cell_measurement_theta_max      34.060

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.750
_shelx_estimated_absorpt_T_min   0.721
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Agilent SuperNova dual radiation CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_reflns_number            27961
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.248
_diffrn_reflns_theta_max         33.727
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7970
_reflns_number_gt                6177
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Rigaku, 2015)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku, 2015)'
_computing_data_reduction        'CrysAlis PRO (Rigaku, 2015)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+0.5517P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7970
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.98121(16) 0.81948(16) 0.80269(16) 0.0256(4) Uani 1 1 d . . . . .
C4 C 1.21043(17) 0.65703(16) 0.80594(16) 0.0282(4) Uani 1 1 d . . . . .
H4 H 1.2457 0.6380 0.7558 0.034 Uiso 1 1 calc R U . . .
C5 C 1.24809(18) 0.62029(15) 0.90875(17) 0.0309(4) Uani 1 1 d . . . . .
H5A H 1.3108 0.5751 0.9308 0.037 Uiso 1 1 calc R U . . .
C6 C 1.19602(19) 0.64780(16) 0.98437(16) 0.0323(5) Uani 1 1 d . . . . .
H6 H 1.2231 0.6194 1.0556 0.039 Uiso 1 1 calc R U . . .
C7 C 1.10938(17) 0.71321(16) 0.95648(14) 0.0283(4) Uani 1 1 d . . . . .
H7A H 1.0752 0.7331 1.0073 0.034 Uiso 1 1 calc R U . . .
C9 C 1.11692(16) 0.72477(14) 0.77461(14) 0.0216(3) Uani 1 1 d . . . . .
C11 C 0.90953(17) 0.89476(16) 0.61668(17) 0.0316(4) Uani 1 1 d . . . . .
H11A H 0.9486 0.9175 0.5673 0.038 Uiso 1 1 calc R U . . .
H11B H 0.8929 0.9595 0.6513 0.038 Uiso 1 1 calc R U . . .
C12 C 0.80144(17) 0.84135(16) 0.55027(16) 0.0294(4) Uani 1 1 d . . . . .
H12A H 0.7581 0.8905 0.4926 0.035 Uiso 1 1 calc R U . . .
H12B H 0.8172 0.7764 0.5153 0.035 Uiso 1 1 calc R U . . .
C13 C 0.73543(16) 0.81196(15) 0.62129(15) 0.0254(4) Uani 1 1 d . . . . .
H13A H 0.7726 0.7519 0.6685 0.030 Uiso 1 1 calc R U . . .
H13B H 0.7355 0.8734 0.6686 0.030 Uiso 1 1 calc R U . . .
C15 C 0.56770(15) 0.73919(14) 0.64090(14) 0.0219(3) Uani 1 1 d . . . . .
H15A H 0.6085 0.6753 0.6775 0.026 Uiso 1 1 calc R U . . .
H15B H 0.5735 0.7940 0.6967 0.026 Uiso 1 1 calc R U . . .
C16 C 0.44896(15) 0.71087(14) 0.58535(14) 0.0223(3) Uani 1 1 d . . . . .
H16A H 0.4179 0.6830 0.6393 0.027 Uiso 1 1 calc R U . . .
H16B H 0.4073 0.7757 0.5525 0.027 Uiso 1 1 calc R U . . .
C18 C 0.48656(16) 0.66491(15) 0.42253(14) 0.0231(4) Uani 1 1 d . . . . .
H18A H 0.4444 0.7258 0.3806 0.028 Uiso 1 1 calc R U . . .
H18B H 0.4827 0.6059 0.3714 0.028 Uiso 1 1 calc R U . . .
C19 C 0.60572(16) 0.69780(14) 0.47631(14) 0.0227(4) Uani 1 1 d . . . . .
H19A H 0.6499 0.6344 0.5095 0.027 Uiso 1 1 calc R U . . .
H19B H 0.6344 0.7260 0.4207 0.027 Uiso 1 1 calc R U . . .
C20 C 0.33440(15) 0.57861(13) 0.46128(14) 0.0196(3) Uani 1 1 d . . . . .
C21 C 0.29059(15) 0.54411(13) 0.35360(14) 0.0214(3) Uani 1 1 d . . . . .
H21A H 0.3271 0.5601 0.3037 0.026 Uiso 1 1 calc R U . . .
C22 C 0.19338(16) 0.48636(14) 0.32069(15) 0.0237(4) Uani 1 1 d . . . . .
C23 C 0.13461(17) 0.46281(15) 0.38790(18) 0.0285(4) Uani 1 1 d . . . . .
H23A H 0.0674 0.4243 0.3626 0.034 Uiso 1 1 calc R U . . .
C24 C 0.17790(18) 0.49794(16) 0.49438(18) 0.0303(4) Uani 1 1 d . . . . .
H24A H 0.1395 0.4832 0.5429 0.036 Uiso 1 1 calc R U . . .
C25 C 0.27581(17) 0.55397(15) 0.53096(16) 0.0268(4) Uani 1 1 d . . . . .
H25A H 0.3039 0.5762 0.6044 0.032 Uiso 1 1 calc R U . . .
Cl26 Cl 0.14455(4) 0.43918(4) 0.18786(4) 0.03379(11) Uani 1 1 d . . . . .
I31 I 0.51651(2) 0.97372(2) 0.34165(2) 0.02457(4) Uani 1 1 d . . . . .
N2 N 0.98215(14) 0.82617(13) 0.70036(13) 0.0251(3) Uani 1 1 d . . . . .
N3 N 1.06434(14) 0.76897(13) 0.68056(12) 0.0261(3) Uani 1 1 d . . . . .
N8 N 1.07104(13) 0.75105(12) 0.85179(12) 0.0218(3) Uani 1 1 d . . . . .
N14 N 0.61837(12) 0.78074(11) 0.56142(12) 0.0202(3) Uani 1 1 d . . . . .
H14A H 0.5770 0.8458 0.5261 0.024 Uiso 1 1 calc R U . . .
N17 N 0.43651(13) 0.63076(11) 0.50123(11) 0.0199(3) Uani 1 1 d . . . . .
O10 O 0.92036(13) 0.85917(14) 0.84516(12) 0.0401(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O10 1.215(2) . ?
C1 N2 1.351(2) . ?
C1 N8 1.412(3) . ?
C4 C5 1.352(3) . ?
C4 C9 1.420(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.419(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.335(3) . ?
C6 H6 0.9500 . ?
C7 N8 1.379(2) . ?
C7 H7A 0.9500 . ?
C9 N3 1.314(2) . ?
C9 N8 1.377(2) . ?
C11 N2 1.459(2) . ?
C11 C12 1.528(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.508(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N14 1.501(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 C16 1.502(3) . ?
C15 N14 1.502(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N17 1.462(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 N17 1.458(2) . ?
C18 C19 1.518(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N14 1.495(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.402(2) . ?
C20 N17 1.406(2) . ?
C20 C25 1.406(3) . ?
C21 C22 1.387(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.378(3) . ?
C22 Cl26 1.7455(19) . ?
C23 C24 1.390(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
N2 N3 1.378(2) . ?
N14 H14A 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O10 C1 N2 131.1(2) . . ?
O10 C1 N8 126.85(19) . . ?
N2 C1 N8 102.04(16) . . ?
C5 C4 C9 118.44(19) . . ?
C5 C4 H4 120.8 . . ?
C9 C4 H4 120.8 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C7 C6 C5 120.68(18) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 N8 118.00(19) . . ?
C6 C7 H7A 121.0 . . ?
N8 C7 H7A 121.0 . . ?
N3 C9 N8 112.13(17) . . ?
N3 C9 C4 130.02(18) . . ?
N8 C9 C4 117.84(16) . . ?
N2 C11 C12 113.66(16) . . ?
N2 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N2 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 110.71(17) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N14 C13 C12 114.90(15) . . ?
N14 C13 H13A 108.5 . . ?
C12 C13 H13A 108.5 . . ?
N14 C13 H13B 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C16 C15 N14 111.06(14) . . ?
C16 C15 H15A 109.4 . . ?
N14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
N14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N17 C16 C15 111.23(15) . . ?
N17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
N17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N17 C18 C19 111.99(14) . . ?
N17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
N17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
N14 C19 C18 111.92(15) . . ?
N14 C19 H19A 109.2 . . ?
C18 C19 H19A 109.2 . . ?
N14 C19 H19B 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 N17 121.80(16) . . ?
C21 C20 C25 117.83(17) . . ?
N17 C20 C25 120.28(16) . . ?
C22 C21 C20 119.26(17) . . ?
C22 C21 H21A 120.4 . . ?
C20 C21 H21A 120.4 . . ?
C23 C22 C21 123.41(18) . . ?
C23 C22 Cl26 118.49(15) . . ?
C21 C22 Cl26 118.09(15) . . ?
C22 C23 C24 117.11(18) . . ?
C22 C23 H23A 121.4 . . ?
C24 C23 H23A 121.4 . . ?
C25 C24 C23 121.25(19) . . ?
C25 C24 H24A 119.4 . . ?
C23 C24 H24A 119.4 . . ?
C24 C25 C20 121.12(18) . . ?
C24 C25 H25A 119.4 . . ?
C20 C25 H25A 119.4 . . ?
C1 N2 N3 115.05(16) . . ?
C1 N2 C11 124.43(18) . . ?
N3 N2 C11 120.32(16) . . ?
C9 N3 N2 103.18(15) . . ?
C9 N8 C7 123.59(17) . . ?
C9 N8 C1 107.59(15) . . ?
C7 N8 C1 128.81(17) . . ?
C19 N14 C13 114.09(15) . . ?
C19 N14 C15 108.40(13) . . ?
C13 N14 C15 109.04(14) . . ?
C19 N14 H14A 108.4 . . ?
C13 N14 H14A 108.4 . . ?
C15 N14 H14A 108.4 . . ?
C20 N17 C18 117.30(14) . . ?
C20 N17 C16 116.79(15) . . ?
C18 N17 C16 111.88(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C5 C6 C7 N8 1.4(3) . . . . ?
C5 C4 C9 N3 -178.9(2) . . . . ?
C5 C4 C9 N8 1.3(3) . . . . ?
N2 C11 C12 C13 62.3(2) . . . . ?
C11 C12 C13 N14 167.50(15) . . . . ?
N14 C15 C16 N17 58.45(19) . . . . ?
N17 C18 C19 N14 -54.2(2) . . . . ?
N17 C20 C21 C22 175.39(16) . . . . ?
C25 C20 C21 C22 -1.0(3) . . . . ?
C20 C21 C22 C23 1.8(3) . . . . ?
C20 C21 C22 Cl26 -177.00(13) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
Cl26 C22 C23 C24 177.54(15) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 0.8(3) . . . . ?
C21 C20 C25 C24 -0.3(3) . . . . ?
N17 C20 C25 C24 -176.71(18) . . . . ?
O10 C1 N2 N3 -179.6(2) . . . . ?
N8 C1 N2 N3 -0.3(2) . . . . ?
O10 C1 N2 C11 5.5(3) . . . . ?
N8 C1 N2 C11 -175.22(17) . . . . ?
C12 C11 N2 C1 -89.9(2) . . . . ?
C12 C11 N2 N3 95.5(2) . . . . ?
N8 C9 N3 N2 0.4(2) . . . . ?
C4 C9 N3 N2 -179.38(19) . . . . ?
C1 N2 N3 C9 0.0(2) . . . . ?
C11 N2 N3 C9 175.08(16) . . . . ?
N3 C9 N8 C7 178.59(17) . . . . ?
C4 C9 N8 C7 -1.6(3) . . . . ?
N3 C9 N8 C1 -0.7(2) . . . . ?
C4 C9 N8 C1 179.17(17) . . . . ?
C6 C7 N8 C9 0.2(3) . . . . ?
C6 C7 N8 C1 179.31(19) . . . . ?
O10 C1 N8 C9 179.9(2) . . . . ?
N2 C1 N8 C9 0.6(2) . . . . ?
O10 C1 N8 C7 0.7(3) . . . . ?
N2 C1 N8 C7 -178.62(18) . . . . ?
C18 C19 N14 C13 176.93(14) . . . . ?
C18 C19 N14 C15 55.24(18) . . . . ?
C12 C13 N14 C19 50.8(2) . . . . ?
C12 C13 N14 C15 172.16(16) . . . . ?
C16 C15 N14 C19 -57.50(18) . . . . ?
C16 C15 N14 C13 177.76(14) . . . . ?
C21 C20 N17 C18 10.7(2) . . . . ?
C25 C20 N17 C18 -173.01(16) . . . . ?
C21 C20 N17 C16 147.63(16) . . . . ?
C25 C20 N17 C16 -36.1(2) . . . . ?
C19 C18 N17 C20 -167.61(15) . . . . ?
C19 C18 N17 C16 53.5(2) . . . . ?
C15 C16 N17 C20 165.06(14) . . . . ?
C15 C16 N17 C18 -55.78(19) . . . . ?

_refine_diff_density_max         0.712
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.095



_exptl_crystal_recrystallization_method 'Vapour diffusion'
