# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_M4CYCLEN_123K
_database_code_depnum_ccdc_archive 'CCDC 1886728'
loop_
_audit_author_name
_audit_author_address
'Alessandro Prescimone'
;University of Basel
Switzerland
;
_audit_update_record             
;
2018-12-21 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;
_audit_creation_date             2018-02-26
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 'M4CYCLEN_123K_0m in P2(1)'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Daniel Joss'

_exptl_crystal_recrystallization_method 
; 
DCM / Et2O / Hexane
;

_refine_special_details          
; 

;
#end of refcif 
_cell_length_a                   9.1262(6)
_cell_length_b                   13.9881(9)
_cell_length_c                   14.5299(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.526(3)
_cell_angle_gamma                90
_cell_volume                     1846.2(2)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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 = C18 H42 Cl1 N6 O1 
# Dc =      1.42 Fooo =    868.00 Mu =     19.99 M =    394.02
# Found Formula = C12 H34 Cl2 N4 O2 
# Dc =      1.21 FOOO =    736.00 Mu =     32.24 M =    337.33

_chemical_formula_sum            'C12 H34 Cl2 N4 O2'
_chemical_formula_moiety         'C12 H34 Cl2 N4 O2'
_chemical_formula_weight         337.33


_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      4
_cell_measurement_theta_max      70
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_max          0.080

_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    3.224

# Sheldrick geometric approximatio 0.82 0.85 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.85
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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      123
_diffrn_reflns_number            22735
_reflns_number_total             6397
_diffrn_reflns_av_R_equivalents  0.047
# Number of reflections without Friedels Law is 6397 
# Number of reflections with Friedels Law is 3617 
# Theoretical number of reflections is about 3530 


_diffrn_reflns_theta_min         4.397
_diffrn_reflns_theta_max         70.423
_diffrn_measured_fraction_theta_max 0.982

_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -11
_reflns_limit_h_max              10
_reflns_limit_k_min              -16
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_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         -0.97
_refine_diff_density_max         0.70


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


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     1
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6336
_oxford_refine_ls_R_factor_ref   0.0649
_refine_ls_wR_factor_ref         0.1473
_refine_ls_goodness_of_fit_ref   1.2469
_refine_ls_shift/su_max          0.0006635
_refine_ls_shift/su_mean         0.0000666


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6336
_refine_ls_R_factor_all          0.0649
_refine_ls_wR_factor_all         0.1473

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6083
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_gt          0.1467

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661\"i?1/2683 
_oxford_Hooft_y                  0.128(6) # for 2682 Friedel pairs 
_oxford_Bijvoet_difference       0.117(7) # for 2682 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.113(12) # for 2780 Friedel pairs 
_refine_ls_abs_structure_Flack   0.117(7)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 2682 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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 6.79 9.48 3.17 
;

# 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 0.69794(8) 0.65241(7) 0.71270(5) 0.0336 1.0000 Uani . . . . . .
Cl2 Cl 0.30138(8) 0.50009(7) 0.79140(5) 0.0289 1.0000 Uani . . . . . .
Cl3 Cl 1.13402(7) 0.74709(7) 0.57416(4) 0.0251 1.0000 Uani . . . . . .
Cl4 Cl 0.87431(8) 0.45497(7) 0.93548(5) 0.0324 1.0000 Uani . . . . . .
O5 O 0.8168(3) 0.85470(19) 0.05575(17) 0.0364 1.0000 Uani . . . . . .
O6 O -0.2098(3) 0.8013(2) 0.5643(2) 0.0520 1.0000 Uani . . . . . .
O7 O 0.5509(3) 0.1718(2) 0.45459(17) 0.0375 1.0000 Uani . . . . . .
O8 O 0.4592(3) 0.9007(2) 1.0689(2) 0.0422 1.0000 Uani . . . . . .
N9 N 0.8830(2) 0.56055(17) 0.50095(16) 0.0197 1.0000 Uani . . . . . .
C10 C 0.7479(3) 0.5594(2) 0.4380(2) 0.0208 1.0000 Uani . . . . . .
C11 C 0.6448(3) 0.4793(2) 0.45974(19) 0.0216 1.0000 Uani . . . . . .
N12 N 0.6010(2) 0.4960(2) 0.55465(16) 0.0238 1.0000 Uani . . . . . .
C13 C 0.5369(3) 0.4135(3) 0.6037(2) 0.0262 1.0000 Uani . . . . . .
C14 C 0.6529(3) 0.3429(2) 0.6400(2) 0.0265 1.0000 Uani . . . . . .
N15 N 0.7703(3) 0.3952(2) 0.69329(17) 0.0285 1.0000 Uani . . . . . .
C16 C 0.9044(3) 0.3399(2) 0.7154(2) 0.0267 1.0000 Uani . . . . . .
C17 C 1.0108(3) 0.3516(2) 0.64114(19) 0.0228 1.0000 Uani . . . . . .
N18 N 1.0493(3) 0.4553(2) 0.63882(17) 0.0241 1.0000 Uani . . . . . .
C19 C 1.1174(3) 0.4891(2) 0.5542(2) 0.0275 1.0000 Uani . . . . . .
C20 C 1.0023(3) 0.5024(2) 0.47254(18) 0.0219 1.0000 Uani . . . . . .
C21 C 1.0774(3) 0.5433(2) 0.3911(2) 0.0285 1.0000 Uani . . . . . .
C22 C 1.1476(4) 0.2920(2) 0.6631(2) 0.0288 1.0000 Uani . . . . . .
C23 C 0.5787(4) 0.2657(3) 0.6948(3) 0.0387 1.0000 Uani . . . . . .
C24 C 0.5074(3) 0.4757(3) 0.3919(2) 0.0338 1.0000 Uani . . . . . .
N25 N 0.3841(2) 0.58441(18) 1.01180(14) 0.0194 1.0000 Uani . . . . . .
C26 C 0.2632(3) 0.5796(2) 1.0707(2) 0.0247 1.0000 Uani . . . . . .
C27 C 0.1449(3) 0.6524(2) 1.0430(2) 0.0250 1.0000 Uani . . . . . .
N28 N 0.0877(2) 0.63287(19) 0.94320(16) 0.0230 1.0000 Uani . . . . . .
C29 C 0.0002(3) 0.7124(2) 0.8940(2) 0.0268 1.0000 Uani . . . . . .
C30 C 0.1021(3) 0.7895(2) 0.8615(2) 0.0260 1.0000 Uani . . . . . .
N31 N 0.2107(3) 0.7432(2) 0.80710(17) 0.0238 1.0000 Uani . . . . . .
C32 C 0.3344(3) 0.8016(2) 0.79090(19) 0.0254 1.0000 Uani . . . . . .
C33 C 0.4586(3) 0.7937(2) 0.8678(2) 0.0252 1.0000 Uani . . . . . .
N34 N 0.5065(3) 0.69035(18) 0.87354(16) 0.0226 1.0000 Uani . . . . . .
C35 C 0.5978(3) 0.6631(2) 0.96108(19) 0.0234 1.0000 Uani . . . . . .
C36 C 0.5037(3) 0.6498(2) 1.04176(18) 0.0194 1.0000 Uani . . . . . .
C37 C 0.6039(3) 0.6180(3) 1.1268(2) 0.0312 1.0000 Uani . . . . . .
C38 C 0.5873(3) 0.8576(3) 0.8515(2) 0.0323 1.0000 Uani . . . . . .
C39 C 0.0073(4) 0.8659(3) 0.8097(2) 0.0391 1.0000 Uani . . . . . .
C40 C 0.0169(4) 0.6439(3) 1.1043(2) 0.0295 1.0000 Uani . . . . . .
H102 H 0.6993 0.6189 0.4472 0.0278 1.0000 Uiso R . . . . .
H101 H 0.7695 0.5558 0.3740 0.0280 1.0000 Uiso R . . . . .
H111 H 0.6958 0.4178 0.4591 0.0274 1.0000 Uiso R . . . . .
H131 H 0.4890 0.4372 0.6551 0.0337 1.0000 Uiso R . . . . .
H132 H 0.4680 0.3809 0.5604 0.0335 1.0000 Uiso R . . . . .
H141 H 0.6925 0.3121 0.5858 0.0339 1.0000 Uiso R . . . . .
H162 H 0.9531 0.3596 0.7733 0.0342 1.0000 Uiso R . . . . .
H161 H 0.8814 0.2720 0.7215 0.0334 1.0000 Uiso R . . . . .
H171 H 0.9621 0.3335 0.5799 0.0290 1.0000 Uiso R . . . . .
H192 H 1.1648 0.5497 0.5690 0.0326 1.0000 Uiso R . . . . .
H191 H 1.1886 0.4438 0.5388 0.0334 1.0000 Uiso R . . . . .
H201 H 0.9666 0.4381 0.4566 0.0257 1.0000 Uiso R . . . . .
H211 H 1.0081 0.5506 0.3373 0.0414 1.0000 Uiso R . . . . .
H212 H 1.1202 0.6055 0.4072 0.0416 1.0000 Uiso R . . . . .
H213 H 1.1549 0.5005 0.3751 0.0420 1.0000 Uiso R . . . . .
H223 H 1.2079 0.2983 0.6132 0.0437 1.0000 Uiso R . . . . .
H221 H 1.2004 0.3133 0.7192 0.0443 1.0000 Uiso R . . . . .
H222 H 1.1233 0.2269 0.6697 0.0438 1.0000 Uiso R . . . . .
H233 H 0.6470 0.2174 0.7174 0.0575 1.0000 Uiso R . . . . .
H232 H 0.5356 0.2932 0.7468 0.0581 1.0000 Uiso R . . . . .
H231 H 0.5028 0.2350 0.6538 0.0576 1.0000 Uiso R . . . . .
H241 H 0.4491 0.4199 0.4036 0.0490 1.0000 Uiso R . . . . .
H243 H 0.4515 0.5329 0.4002 0.0492 1.0000 Uiso R . . . . .
H242 H 0.5353 0.4744 0.3299 0.0490 1.0000 Uiso R . . . . .
H262 H 0.2979 0.5862 1.1362 0.0291 1.0000 Uiso R . . . . .
H261 H 0.2197 0.5166 1.0601 0.0287 1.0000 Uiso R . . . . .
H271 H 0.1832 0.7171 1.0453 0.0301 1.0000 Uiso R . . . . .
H291 H -0.0649 0.7397 0.9351 0.0321 1.0000 Uiso R . . . . .
H292 H -0.0570 0.6842 0.8418 0.0318 1.0000 Uiso R . . . . .
H301 H 0.1569 0.8195 0.9163 0.0326 1.0000 Uiso R . . . . .
H321 H 0.3027 0.8678 0.7830 0.0331 1.0000 Uiso R . . . . .
H322 H 0.3681 0.7804 0.7332 0.0331 1.0000 Uiso R . . . . .
H331 H 0.4221 0.8114 0.9265 0.0308 1.0000 Uiso R . . . . .
H351 H 0.6692 0.7129 0.9766 0.0300 1.0000 Uiso R . . . . .
H352 H 0.6464 0.6027 0.9505 0.0298 1.0000 Uiso R . . . . .
H361 H 0.4550 0.7099 1.0543 0.0244 1.0000 Uiso R . . . . .
H372 H 0.5500 0.6083 1.1789 0.0480 1.0000 Uiso R . . . . .
H371 H 0.6793 0.6638 1.1424 0.0474 1.0000 Uiso R . . . . .
H373 H 0.6490 0.5581 1.1131 0.0479 1.0000 Uiso R . . . . .
H381 H 0.6537 0.8589 0.9066 0.0471 1.0000 Uiso R . . . . .
H383 H 0.5543 0.9209 0.8379 0.0469 1.0000 Uiso R . . . . .
H382 H 0.6367 0.8344 0.8012 0.0465 1.0000 Uiso R . . . . .
H392 H 0.0707 0.9139 0.7884 0.0577 1.0000 Uiso R . . . . .
H391 H -0.0574 0.8930 0.8510 0.0577 1.0000 Uiso R . . . . .
H393 H -0.0494 0.8365 0.7575 0.0577 1.0000 Uiso R . . . . .
H401 H -0.0454 0.6969 1.0905 0.0447 1.0000 Uiso R . . . . .
H403 H 0.0556 0.6434 1.1686 0.0447 1.0000 Uiso R . . . . .
H402 H -0.0319 0.5848 1.0880 0.0444 1.0000 Uiso R . . . . .
H181 H 1.1061 0.4708 0.6887 0.0357 1.0000 Uiso R . . . . .
H341 H 0.4285 0.6516 0.8628 0.0358 1.0000 Uiso R . . . . .
H282 H 0.1621 0.6167 0.9122 0.0357 1.0000 Uiso R . . . . .
H311 H 0.1676 0.7260 0.7548 0.0280 1.0000 Uiso R . . . . .
H342 H 0.5576 0.6774 0.8248 0.0353 1.0000 Uiso R . . . . .
H251 H 0.4228 0.5289 1.0101 0.0258 1.0000 Uiso R . . . . .
H281 H 0.0331 0.5795 0.9391 0.0353 1.0000 Uiso R . . . . .
H151 H 0.7435 0.4218 0.7403 0.0334 1.0000 Uiso R . . . . .
H72 H 0.6352 0.1865 0.4514 0.0575 1.0000 Uiso R . . . . .
H182 H 0.9666 0.4882 0.6427 0.0359 1.0000 Uiso R . . . . .
H82 H 0.3579 0.9198 1.0751 0.0645 1.0000 Uiso R . . . . .
H91 H 0.9100 0.6174 0.5117 0.0264 1.0000 Uiso R . . . . .
H122 H 0.6776 0.5179 0.5895 0.0348 1.0000 Uiso R . . . . .
H81 H 0.4783 0.9207 1.1218 0.0649 1.0000 Uiso R . . . . .
H51 H 0.7717 0.8758 0.0971 0.0572 1.0000 Uiso R . . . . .
H121 H 0.5450 0.5465 0.5562 0.0348 1.0000 Uiso R . . . . .
H61 H -0.2221 0.7603 0.6078 0.0769 1.0000 Uiso R . . . . .
H62 H -0.1136 0.7863 0.5671 0.0619 1.0000 Uiso R . . . . .
H52 H 0.9053 0.8834 0.0583 0.0460 1.0000 Uiso R . . . . .
H71 H 0.4650 0.2044 0.4498 0.0450 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2200(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
O5 . H51 . 0.815 no
O5 . H52 . 0.900 no
O6 . H61 . 0.868 no
O6 . H62 . 0.900 no
O7 . H72 . 0.802 no
O7 . H71 . 0.904 no
O8 . H82 . 0.975 no
O8 . H81 . 0.822 no
N9 . C10 . 1.463(3) yes
N9 . C20 . 1.450(3) yes
N9 . H91 . 0.843 no
C10 . C11 . 1.516(4) yes
C10 . H102 . 0.958 no
C10 . H101 . 0.970 no
C11 . N12 . 1.491(3) yes
C11 . C24 . 1.520(4) yes
C11 . H111 . 0.978 no
N12 . C13 . 1.504(4) yes
N12 . H122 . 0.878 no
N12 . H121 . 0.874 no
C13 . C14 . 1.505(4) yes
C13 . H131 . 0.960 no
C13 . H132 . 0.961 no
C14 . N15 . 1.457(4) yes
C14 . C23 . 1.537(5) yes
C14 . H141 . 0.995 no
N15 . C16 . 1.457(4) yes
N15 . H151 . 0.835 no
C16 . C17 . 1.528(4) yes
C16 . H162 . 0.954 no
C16 . H161 . 0.979 no
C17 . N18 . 1.494(4) yes
C17 . C22 . 1.509(4) yes
C17 . H171 . 0.988 no
N18 . C19 . 1.506(4) yes
N18 . H181 . 0.876 no
N18 . H182 . 0.890 no
C19 . C20 . 1.519(4) yes
C19 . H192 . 0.966 no
C19 . H191 . 0.950 no
C20 . C21 . 1.534(4) yes
C20 . H201 . 0.976 no
C21 . H211 . 0.962 no
C21 . H212 . 0.973 no
C21 . H213 . 0.971 no
C22 . H223 . 0.956 no
C22 . H221 . 0.953 no
C22 . H222 . 0.945 no
C23 . H233 . 0.956 no
C23 . H232 . 0.965 no
C23 . H231 . 0.970 no
C24 . H241 . 0.969 no
C24 . H243 . 0.963 no
C24 . H242 . 0.960 no
N25 . C26 . 1.462(3) yes
N25 . C36 . 1.458(4) yes
N25 . H251 . 0.854 no
C26 . C27 . 1.510(4) yes
C26 . H262 . 0.978 no
C26 . H261 . 0.972 no
C27 . N28 . 1.517(4) yes
C27 . C40 . 1.541(4) yes
C27 . H271 . 0.971 no
N28 . C29 . 1.508(4) yes
N28 . H282 . 0.880 no
N28 . H281 . 0.897 no
C29 . C30 . 1.528(5) yes
C29 . H291 . 0.961 no
C29 . H292 . 0.963 no
C30 . N31 . 1.475(4) yes
C30 . C39 . 1.527(4) yes
C30 . H301 . 0.991 no
N31 . C32 . 1.430(4) yes
N31 . H311 . 0.856 no
C32 . C33 . 1.517(4) yes
C32 . H321 . 0.975 no
C32 . H322 . 0.967 no
C33 . N34 . 1.510(4) yes
C33 . C38 . 1.512(4) yes
C33 . H331 . 0.977 no
N34 . C35 . 1.501(4) yes
N34 . H341 . 0.897 no
N34 . H342 . 0.904 no
C35 . C36 . 1.530(3) yes
C35 . H351 . 0.966 no
C35 . H352 . 0.972 no
C36 . C37 . 1.530(4) yes
C36 . H361 . 0.976 no
C37 . H372 . 0.951 no
C37 . H371 . 0.952 no
C37 . H373 . 0.963 no
C38 . H381 . 0.957 no
C38 . H383 . 0.951 no
C38 . H382 . 0.951 no
C39 . H392 . 0.957 no
C39 . H391 . 0.960 no
C39 . H393 . 0.968 no
C40 . H401 . 0.944 no
C40 . H403 . 0.966 no
C40 . H402 . 0.959 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
H51 . O5 . H52 . 108.8 no
H61 . O6 . H62 . 90.5 no
H72 . O7 . H71 . 134.1 no
H82 . O8 . H81 . 86.4 no
C10 . N9 . C20 . 115.2(2) yes
C10 . N9 . H91 . 109.9 no
C20 . N9 . H91 . 111.6 no
N9 . C10 . C11 . 112.3(2) yes
N9 . C10 . H102 . 106.0 no
C11 . C10 . H102 . 107.9 no
N9 . C10 . H101 . 111.3 no
C11 . C10 . H101 . 110.4 no
H102 . C10 . H101 . 108.7 no
C10 . C11 . N12 . 107.7(2) yes
C10 . C11 . C24 . 112.3(3) yes
N12 . C11 . C24 . 109.1(2) yes
C10 . C11 . H111 . 110.0 no
N12 . C11 . H111 . 108.4 no
C24 . C11 . H111 . 109.2 no
C11 . N12 . C13 . 118.0(2) yes
C11 . N12 . H122 . 108.6 no
C13 . N12 . H122 . 108.5 no
C11 . N12 . H121 . 111.1 no
C13 . N12 . H121 . 110.7 no
H122 . N12 . H121 . 97.9 no
N12 . C13 . C14 . 112.2(2) yes
N12 . C13 . H131 . 109.3 no
C14 . C13 . H131 . 108.2 no
N12 . C13 . H132 . 108.3 no
C14 . C13 . H132 . 108.1 no
H131 . C13 . H132 . 110.8 no
C13 . C14 . N15 . 108.3(3) yes
C13 . C14 . C23 . 108.2(2) yes
N15 . C14 . C23 . 114.5(3) yes
C13 . C14 . H141 . 107.7 no
N15 . C14 . H141 . 109.4 no
C23 . C14 . H141 . 108.5 no
C14 . N15 . C16 . 114.2(3) yes
C14 . N15 . H151 . 113.6 no
C16 . N15 . H151 . 111.3 no
N15 . C16 . C17 . 111.4(2) yes
N15 . C16 . H162 . 110.5 no
C17 . C16 . H162 . 108.6 no
N15 . C16 . H161 . 110.6 no
C17 . C16 . H161 . 108.9 no
H162 . C16 . H161 . 106.6 no
C16 . C17 . N18 . 106.7(2) yes
C16 . C17 . C22 . 111.1(3) yes
N18 . C17 . C22 . 110.5(2) yes
C16 . C17 . H171 . 110.3 no
N18 . C17 . H171 . 108.4 no
C22 . C17 . H171 . 109.9 no
C17 . N18 . C19 . 116.1(2) yes
C17 . N18 . H181 . 110.1 no
C19 . N18 . H181 . 109.9 no
C17 . N18 . H182 . 107.3 no
C19 . N18 . H182 . 108.0 no
H181 . N18 . H182 . 104.9 no
N18 . C19 . C20 . 111.6(2) yes
N18 . C19 . H192 . 107.8 no
C20 . C19 . H192 . 109.1 no
N18 . C19 . H191 . 109.2 no
C20 . C19 . H191 . 109.6 no
H192 . C19 . H191 . 109.6 no
C19 . C20 . N9 . 109.1(2) yes
C19 . C20 . C21 . 108.7(2) yes
N9 . C20 . C21 . 114.5(2) yes
C19 . C20 . H201 . 105.2 no
N9 . C20 . H201 . 110.0 no
C21 . C20 . H201 . 108.9 no
C20 . C21 . H211 . 110.9 no
C20 . C21 . H212 . 110.3 no
H211 . C21 . H212 . 108.5 no
C20 . C21 . H213 . 110.2 no
H211 . C21 . H213 . 107.9 no
H212 . C21 . H213 . 108.9 no
C17 . C22 . H223 . 108.2 no
C17 . C22 . H221 . 110.4 no
H223 . C22 . H221 . 109.8 no
C17 . C22 . H222 . 110.9 no
H223 . C22 . H222 . 108.9 no
H221 . C22 . H222 . 108.5 no
C14 . C23 . H233 . 111.7 no
C14 . C23 . H232 . 111.1 no
H233 . C23 . H232 . 108.3 no
C14 . C23 . H231 . 108.4 no
H233 . C23 . H231 . 107.6 no
H232 . C23 . H231 . 109.6 no
C11 . C24 . H241 . 110.2 no
C11 . C24 . H243 . 107.8 no
H241 . C24 . H243 . 110.0 no
C11 . C24 . H242 . 109.4 no
H241 . C24 . H242 . 110.5 no
H243 . C24 . H242 . 109.0 no
C26 . N25 . C36 . 116.1(2) yes
C26 . N25 . H251 . 108.2 no
C36 . N25 . H251 . 106.2 no
N25 . C26 . C27 . 111.9(2) yes
N25 . C26 . H262 . 111.9 no
C27 . C26 . H262 . 110.6 no
N25 . C26 . H261 . 105.6 no
C27 . C26 . H261 . 107.4 no
H262 . C26 . H261 . 109.2 no
C26 . C27 . N28 . 107.8(2) yes
C26 . C27 . C40 . 110.9(3) yes
N28 . C27 . C40 . 109.2(2) yes
C26 . C27 . H271 . 112.0 no
N28 . C27 . H271 . 106.9 no
C40 . C27 . H271 . 110.0 no
C27 . N28 . C29 . 116.0(2) yes
C27 . N28 . H282 . 108.9 no
C29 . N28 . H282 . 110.3 no
C27 . N28 . H281 . 110.6 no
C29 . N28 . H281 . 108.5 no
H282 . N28 . H281 . 101.7 no
N28 . C29 . C30 . 110.9(2) yes
N28 . C29 . H291 . 109.2 no
C30 . C29 . H291 . 110.1 no
N28 . C29 . H292 . 107.1 no
C30 . C29 . H292 . 110.2 no
H291 . C29 . H292 . 109.4 no
C29 . C30 . N31 . 108.5(3) yes
C29 . C30 . C39 . 108.2(3) yes
N31 . C30 . C39 . 114.9(2) yes
C29 . C30 . H301 . 109.0 no
N31 . C30 . H301 . 107.6 no
C39 . C30 . H301 . 108.5 no
C30 . N31 . C32 . 114.8(3) yes
C30 . N31 . H311 . 108.9 no
C32 . N31 . H311 . 108.5 no
N31 . C32 . C33 . 112.5(2) yes
N31 . C32 . H321 . 109.4 no
C33 . C32 . H321 . 110.4 no
N31 . C32 . H322 . 106.9 no
C33 . C32 . H322 . 109.7 no
H321 . C32 . H322 . 107.7 no
C32 . C33 . N34 . 107.6(2) yes
C32 . C33 . C38 . 112.3(2) yes
N34 . C33 . C38 . 110.5(3) yes
C32 . C33 . H331 . 109.3 no
N34 . C33 . H331 . 108.3 no
C38 . C33 . H331 . 108.8 no
C33 . N34 . C35 . 115.1(2) yes
C33 . N34 . H341 . 110.5 no
C35 . N34 . H341 . 111.2 no
C33 . N34 . H342 . 108.5 no
C35 . N34 . H342 . 109.1 no
H341 . N34 . H342 . 101.7 no
N34 . C35 . C36 . 111.9(2) yes
N34 . C35 . H351 . 108.7 no
C36 . C35 . H351 . 108.9 no
N34 . C35 . H352 . 108.1 no
C36 . C35 . H352 . 108.3 no
H351 . C35 . H352 . 110.9 no
C35 . C36 . N25 . 107.9(2) yes
C35 . C36 . C37 . 108.5(2) yes
N25 . C36 . C37 . 115.5(3) yes
C35 . C36 . H361 . 109.7 no
N25 . C36 . H361 . 104.8 no
C37 . C36 . H361 . 110.3 no
C36 . C37 . H372 . 111.7 no
C36 . C37 . H371 . 111.1 no
H372 . C37 . H371 . 108.9 no
C36 . C37 . H373 . 108.7 no
H372 . C37 . H373 . 107.6 no
H371 . C37 . H373 . 108.7 no
C33 . C38 . H381 . 108.6 no
C33 . C38 . H383 . 110.3 no
H381 . C38 . H383 . 108.5 no
C33 . C38 . H382 . 110.6 no
H381 . C38 . H382 . 110.0 no
H383 . C38 . H382 . 108.8 no
C30 . C39 . H392 . 108.6 no
C30 . C39 . H391 . 108.8 no
H392 . C39 . H391 . 110.6 no
C30 . C39 . H393 . 109.0 no
H392 . C39 . H393 . 109.7 no
H391 . C39 . H393 . 110.1 no
C27 . C40 . H401 . 107.0 no
C27 . C40 . H403 . 109.4 no
H401 . C40 . H403 . 111.7 no
C27 . C40 . H402 . 106.5 no
H401 . C40 . H402 . 111.6 no
H403 . C40 . H402 . 110.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C19 . H191 . O6 2_646 140 0.95 2.51 3.295(4) yes
C22 . H223 . O6 2_646 145 0.96 2.58 3.409(4) yes
C33 . H331 . O8 . 148 0.98 2.41 3.282(4) yes
C38 . H381 . O5 1_556 176 0.96 2.51 3.464(4) yes
C40 . H401 . O5 1_456 172 0.94 2.57 3.504(4) yes
N25 . H251 . O8 2_647 152 0.85 2.44 3.217(4) yes
N12 . H121 . O7 2_656 168 0.87 1.96 2.819(4) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
3 13 0 x .
3 -13 0 x .
-3 2 1 x .
-3 -2 1 x .
3 0 5 x .
3 -9 1 x .
-3 0 3 x .
0 -1 4 x .
0 1 4 x .
3 14 5 x .
-3 -7 14 x .
3 -10 3 x .
-3 0 17 x .
-1 14 4 x .
-3 -14 1 x .
-3 7 14 x .
-3 -6 15 x .
10 -5 4 x .
0 -14 2 x .
0 -8 6 x .
0 14 2 x .
10 -5 0 x .
9 0 1 x .
10 5 0 x .
-1 -4 8 x .
-1 -14 4 x .
4 1 2 x .
4 1 2 x .
-3 -5 5 x .
-10 0 3 x .
-3 6 15 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# 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_FT057_123K
_database_code_depnum_ccdc_archive 'CCDC 1886729'
loop_
_audit_author_name
_audit_author_address
'Alessandro Prescimone'
;University of Basel
Switzerland
;
_audit_update_record             
;
2018-12-21 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;
_audit_creation_date             2018-04-20
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 'FT057_123K_0m in C2'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Thomas Muentener'

_exptl_crystal_recrystallization_method 
; 
;

_refine_special_details          
; 
? 
;
#end of refcif 
_cell_length_a                   9.5648(11)
_cell_length_b                   19.708(2)
_cell_length_c                   9.8034(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.271(4)
_cell_angle_gamma                90
_cell_volume                     1782.7(4)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C16 H36 N4 
# Dc =      1.06 Fooo =    640.00 Mu =      4.83 M =    284.49
# Found Formula = C16 H36 N4 
# Dc =      1.06 FOOO =    640.00 Mu =      4.83 M =    284.49

_chemical_formula_sum            'C16 H36 N4'
_chemical_formula_moiety         'C16 H36 N4'
_chemical_formula_weight         284.49


_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      4
_cell_measurement_theta_max      70
_cell_measurement_temperature    123

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.030
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.120

_exptl_crystal_density_diffrn    1.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.483

# Sheldrick geometric approximatio 1.00 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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      123
_diffrn_reflns_number            10762
_reflns_number_total             3083
_diffrn_reflns_av_R_equivalents  0.030
# Number of reflections without Friedels Law is 3083 
# Number of reflections with Friedels Law is 1694 
# Theoretical number of reflections is about 1689 


_diffrn_reflns_theta_min         4.487
_diffrn_reflns_theta_max         69.961
_diffrn_measured_fraction_theta_max 0.971

_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_full 0.993


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              -21
_reflns_limit_k_max              23
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_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         -0.12
_refine_diff_density_max         0.14


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


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     1
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3070
_oxford_refine_ls_R_factor_ref   0.0264
_refine_ls_wR_factor_ref         0.0589
_refine_ls_goodness_of_fit_ref   0.8694
_refine_ls_shift/su_max          0.0002863
_refine_ls_shift/su_mean         0.0000263


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3070
_refine_ls_R_factor_all          0.0264
_refine_ls_wR_factor_all         0.0589

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3041
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_gt          0.0588

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661683 
_oxford_Hooft_y                  0.06(10) # for 1285 Friedel pairs 
_oxford_Bijvoet_difference       0.08(10) # for 1285 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.0(3) # for 1389 Friedel pairs 
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1285 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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 2.97 4.43 2.03 0.497 
;

# 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 0.19633(10) 0.35140(8) 0.16015(9) 0.0177 1.0000 Uani . . . . . .
C2 C 0.14236(12) 0.30048(8) 0.24255(12) 0.0174 1.0000 Uani . . . . . .
C3 C 0.26107(13) 0.28100(9) 0.37735(12) 0.0224 1.0000 Uani . . . . . .
C4 C 0.30036(13) 0.33872(9) 0.48401(12) 0.0295 1.0000 Uani . . . . . .
C5 C 0.22024(15) 0.21661(9) 0.44452(14) 0.0299 1.0000 Uani . . . . . .
C6 C 0.00669(12) 0.32841(9) 0.27777(12) 0.0198 1.0000 Uani . . . . . .
N7 N -0.10522(10) 0.34857(8) 0.15126(9) 0.0185 1.0000 Uani . . . . . .
C8 C -0.19313(12) 0.29336(9) 0.07090(12) 0.0192 1.0000 Uani . . . . . .
C9 C -0.28166(12) 0.32298(9) -0.06930(12) 0.0191 1.0000 Uani . . . . . .
C10 C -0.29355(15) 0.25900(10) 0.14777(14) 0.0308 1.0000 Uani . . . . . .
N11 N 0.33285(10) 0.48507(8) -0.18342(10) 0.0191 1.0000 Uani . . . . . .
C12 C 0.26217(12) 0.54178(8) -0.13070(12) 0.0183 1.0000 Uani . . . . . .
C13 C 0.13306(12) 0.56925(8) -0.24721(12) 0.0204 1.0000 Uani . . . . . .
C14 C 0.01669(13) 0.51622(9) -0.30520(13) 0.0256 1.0000 Uani . . . . . .
C15 C 0.06984(15) 0.63300(9) -0.19850(14) 0.0278 1.0000 Uani . . . . . .
C16 C 0.21891(13) 0.51733(9) 0.00110(12) 0.0204 1.0000 Uani . . . . . .
N17 N 0.34337(10) 0.49040(8) 0.10816(10) 0.0191 1.0000 Uani . . . . . .
C18 C 0.43381(12) 0.54013(9) 0.20315(12) 0.0199 1.0000 Uani . . . . . .
C19 C 0.57691(13) 0.50516(9) 0.27598(12) 0.0214 1.0000 Uani . . . . . .
C20 C 0.36326(14) 0.56991(9) 0.31291(14) 0.0297 1.0000 Uani . . . . . .
H21 H 0.1163 0.2564 0.1862 0.0177 1.0000 Uiso R . . . . .
H31 H 0.3484 0.2704 0.3446 0.0262 1.0000 Uiso R . . . . .
H41 H 0.3870 0.3266 0.5591 0.0443 1.0000 Uiso R . . . . .
H43 H 0.3196 0.3804 0.4328 0.0454 1.0000 Uiso R . . . . .
H42 H 0.2184 0.3479 0.5271 0.0434 1.0000 Uiso R . . . . .
H52 H 0.3007 0.1992 0.5200 0.0462 1.0000 Uiso R . . . . .
H51 H 0.1398 0.2250 0.4864 0.0449 1.0000 Uiso R . . . . .
H53 H 0.1897 0.1793 0.3728 0.0454 1.0000 Uiso R . . . . .
H62 H 0.0354 0.3695 0.3390 0.0231 1.0000 Uiso R . . . . .
H61 H -0.0320 0.2946 0.3359 0.0242 1.0000 Uiso R . . . . .
H81 H -0.1233 0.2596 0.0503 0.0223 1.0000 Uiso R . . . . .
H91 H -0.3446 0.3598 -0.0482 0.0238 1.0000 Uiso R . . . . .
H92 H -0.3479 0.2868 -0.1228 0.0210 1.0000 Uiso R . . . . .
H101 H -0.3458 0.2201 0.0880 0.0471 1.0000 Uiso R . . . . .
H102 H -0.3618 0.2942 0.1690 0.0470 1.0000 Uiso R . . . . .
H103 H -0.2397 0.2402 0.2392 0.0469 1.0000 Uiso R . . . . .
H121 H 0.3320 0.5806 -0.0993 0.0204 1.0000 Uiso R . . . . .
H131 H 0.1715 0.5836 -0.3267 0.0230 1.0000 Uiso R . . . . .
H142 H -0.0612 0.5348 -0.3879 0.0383 1.0000 Uiso R . . . . .
H141 H -0.0283 0.4999 -0.2316 0.0408 1.0000 Uiso R . . . . .
H143 H 0.0629 0.4760 -0.3370 0.0403 1.0000 Uiso R . . . . .
H151 H 0.0044 0.6561 -0.2774 0.0433 1.0000 Uiso R . . . . .
H153 H 0.1499 0.6657 -0.1568 0.0428 1.0000 Uiso R . . . . .
H152 H 0.0197 0.6210 -0.1242 0.0434 1.0000 Uiso R . . . . .
H161 H 0.1721 0.5562 0.0406 0.0242 1.0000 Uiso R . . . . .
H162 H 0.1468 0.4776 -0.0295 0.0252 1.0000 Uiso R . . . . .
H181 H 0.4538 0.5780 0.1411 0.0230 1.0000 Uiso R . . . . .
H191 H 0.6354 0.5348 0.3527 0.0268 1.0000 Uiso R . . . . .
H192 H 0.5546 0.4647 0.3250 0.0259 1.0000 Uiso R . . . . .
H201 H 0.4264 0.6051 0.3718 0.0445 1.0000 Uiso R . . . . .
H202 H 0.2693 0.5914 0.2671 0.0425 1.0000 Uiso R . . . . .
H203 H 0.3487 0.5335 0.3763 0.0458 1.0000 Uiso R . . . . .
H171 H 0.3142 0.4581 0.1617 0.0237 1.0000 Uiso R . . . . .
H71 H -0.1630 0.3801 0.1744 0.0232 1.0000 Uiso R . . . . .
H11 H 0.1203 0.3735 0.1037 0.0239 1.0000 Uiso R . . . . .
H111 H 0.3919 0.4604 -0.1047 0.0263 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.13377(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 . C9 3_555 1.4684(14) yes
N1 . C2 . 1.4648(15) yes
N1 . H11 . 0.901 no
C2 . C3 . 1.5468(16) yes
C2 . C6 . 1.5304(16) yes
C2 . H21 . 1.024 no
C3 . C4 . 1.5236(18) yes
C3 . C5 . 1.5271(18) yes
C3 . H31 . 0.993 no
C4 . H41 . 0.982 no
C4 . H43 . 1.005 no
C4 . H42 . 1.000 no
C5 . H52 . 0.978 no
C5 . H51 . 0.977 no
C5 . H53 . 1.007 no
C6 . N7 . 1.4637(14) yes
C6 . H62 . 1.003 no
C6 . H61 . 1.008 no
N7 . C8 . 1.4706(15) yes
N7 . H71 . 0.899 no
C8 . C9 . 1.5277(16) yes
C8 . C10 . 1.5265(16) yes
C8 . H81 . 1.001 no
C9 . H91 . 0.999 no
C9 . H92 . 1.005 no
C10 . H101 . 1.013 no
C10 . H102 . 1.011 no
C10 . H103 . 0.981 no
N11 . C19 3_655 1.4620(15) yes
N11 . C12 . 1.4688(15) yes
N11 . H111 . 0.961 no
C12 . C13 . 1.5426(16) yes
C12 . C16 . 1.5344(15) yes
C12 . H121 . 1.009 no
C13 . C14 . 1.5234(16) yes
C13 . C15 . 1.5246(17) yes
C13 . H131 . 0.986 no
C14 . H142 . 1.014 no
C14 . H141 . 0.986 no
C14 . H143 . 0.997 no
C15 . H151 . 0.971 no
C15 . H153 . 1.002 no
C15 . H152 . 1.000 no
C16 . N17 . 1.4636(15) yes
C16 . H161 . 1.014 no
C16 . H162 . 1.033 no
N17 . C18 . 1.4668(15) yes
N17 . H171 . 0.914 no
C18 . C19 . 1.5308(16) yes
C18 . C20 . 1.5298(16) yes
C18 . H181 . 1.012 no
C19 . H191 . 0.999 no
C19 . H192 . 0.984 no
C20 . H201 . 0.998 no
C20 . H202 . 0.988 no
C20 . H203 . 0.982 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
C9 3_555 N1 . C2 . 113.96(9) yes
C9 3_555 N1 . H11 . 107.4 no
C2 . N1 . H11 . 109.0 no
N1 . C2 . C3 . 110.81(9) yes
N1 . C2 . C6 . 108.72(9) yes
C3 . C2 . C6 . 111.83(9) yes
N1 . C2 . H21 . 110.7 no
C3 . C2 . H21 . 105.7 no
C6 . C2 . H21 . 109.0 no
C2 . C3 . C4 . 113.19(10) yes
C2 . C3 . C5 . 111.17(10) yes
C4 . C3 . C5 . 111.67(10) yes
C2 . C3 . H31 . 105.4 no
C4 . C3 . H31 . 107.6 no
C5 . C3 . H31 . 107.3 no
C3 . C4 . H41 . 109.9 no
C3 . C4 . H43 . 108.2 no
H41 . C4 . H43 . 110.1 no
C3 . C4 . H42 . 110.2 no
H41 . C4 . H42 . 109.1 no
H43 . C4 . H42 . 109.3 no
C3 . C5 . H52 . 112.2 no
C3 . C5 . H51 . 111.1 no
H52 . C5 . H51 . 107.0 no
C3 . C5 . H53 . 111.5 no
H52 . C5 . H53 . 107.3 no
H51 . C5 . H53 . 107.5 no
C2 . C6 . N7 . 112.38(9) yes
C2 . C6 . H62 . 108.1 no
N7 . C6 . H62 . 108.2 no
C2 . C6 . H61 . 110.4 no
N7 . C6 . H61 . 111.3 no
H62 . C6 . H61 . 106.2 no
C6 . N7 . C8 . 116.13(9) yes
C6 . N7 . H71 . 109.5 no
C8 . N7 . H71 . 110.1 no
N7 . C8 . C9 . 107.60(10) yes
N7 . C8 . C10 . 114.14(9) yes
C9 . C8 . C10 . 109.99(10) yes
N7 . C8 . H81 . 106.4 no
C9 . C8 . H81 . 108.3 no
C10 . C8 . H81 . 110.1 no
C8 . C9 . N1 3_555 115.25(9) yes
C8 . C9 . H91 . 108.2 no
N1 3_555 C9 . H91 . 108.0 no
C8 . C9 . H92 . 108.8 no
N1 3_555 C9 . H92 . 109.2 no
H91 . C9 . H92 . 107.0 no
C8 . C10 . H101 . 109.2 no
C8 . C10 . H102 . 108.7 no
H101 . C10 . H102 . 113.0 no
C8 . C10 . H103 . 111.8 no
H101 . C10 . H103 . 107.6 no
H102 . C10 . H103 . 106.5 no
C19 3_655 N11 . C12 . 114.46(9) yes
C19 3_655 N11 . H111 . 108.6 no
C12 . N11 . H111 . 109.3 no
N11 . C12 . C13 . 111.06(9) yes
N11 . C12 . C16 . 107.97(9) yes
C13 . C12 . C16 . 113.14(9) yes
N11 . C12 . H121 . 110.8 no
C13 . C12 . H121 . 107.2 no
C16 . C12 . H121 . 106.6 no
C12 . C13 . C14 . 113.53(10) yes
C12 . C13 . C15 . 111.31(10) yes
C14 . C13 . C15 . 111.79(10) yes
C12 . C13 . H131 . 107.0 no
C14 . C13 . H131 . 106.8 no
C15 . C13 . H131 . 105.8 no
C13 . C14 . H142 . 111.2 no
C13 . C14 . H141 . 111.5 no
H142 . C14 . H141 . 109.4 no
C13 . C14 . H143 . 108.8 no
H142 . C14 . H143 . 109.3 no
H141 . C14 . H143 . 106.5 no
C13 . C15 . H151 . 111.2 no
C13 . C15 . H153 . 109.6 no
H151 . C15 . H153 . 106.6 no
C13 . C15 . H152 . 109.8 no
H151 . C15 . H152 . 111.1 no
H153 . C15 . H152 . 108.4 no
C12 . C16 . N17 . 111.65(9) yes
C12 . C16 . H161 . 109.2 no
N17 . C16 . H161 . 110.9 no
C12 . C16 . H162 . 107.5 no
N17 . C16 . H162 . 106.8 no
H161 . C16 . H162 . 110.8 no
C16 . N17 . C18 . 116.44(9) yes
C16 . N17 . H171 . 110.5 no
C18 . N17 . H171 . 108.6 no
N17 . C18 . C19 . 107.50(9) yes
N17 . C18 . C20 . 114.03(9) yes
C19 . C18 . C20 . 110.52(10) yes
N17 . C18 . H181 . 106.5 no
C19 . C18 . H181 . 109.0 no
C20 . C18 . H181 . 109.2 no
C18 . C19 . N11 3_655 115.71(9) yes
C18 . C19 . H191 . 110.1 no
N11 3_655 C19 . H191 . 108.7 no
C18 . C19 . H192 . 108.1 no
N11 3_655 C19 . H192 . 108.9 no
H191 . C19 . H192 . 104.8 no
C18 . C20 . H201 . 111.2 no
C18 . C20 . H202 . 111.2 no
H201 . C20 . H202 . 107.7 no
C18 . C20 . H203 . 109.1 no
H201 . C20 . H203 . 107.8 no
H202 . C20 . H203 . 109.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N17 . H171 . N1 . 146 0.91 2.38 3.181(2) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 

####################################################################### 
# 
# 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_TM11301_A
_database_code_depnum_ccdc_archive 'CCDC 1886730'
loop_
_audit_author_name
_audit_author_address
'Alessandro Prescimone'
;University of Basel
Switzerland
;
_audit_update_record             
;
2018-12-21 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;
_audit_creation_date             2018-01-18
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 'TM11301_A_0m in P2(1)'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Thomas Muentener'

_exptl_crystal_recrystallization_method 
; 
CD2Cl2
;
#end of refcif 
_cell_length_a                   9.0294(5)
_cell_length_b                   14.6457(9)
_cell_length_c                   12.7180(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.439(3)
_cell_angle_gamma                90
_cell_volume                     1613.10(16)

_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'
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 = C12 H28 Cl1 N4 O1 
# Dc =      1.15 Fooo =    612.00 Mu =     20.66 M =    279.83
# Found Formula = C12 H30 Cl1 N4 O1.50 
# Dc =      1.19 FOOO =    636.00 Mu =     21.04 M =    289.85

_chemical_formula_sum            'C12 H30 Cl1 N4 O1.50'
_chemical_formula_moiety         'C12 H30 Cl1 N4 O1.50'
_chemical_formula_weight         289.85


_cell_measurement_reflns_used    8065
_cell_measurement_theta_min      5
_cell_measurement_theta_max      70
_cell_measurement_temperature    123

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.030
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_max          0.090

_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    2.104

# Sheldrick geometric approximatio 0.85 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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      123
_diffrn_reflns_number            11474
_reflns_number_total             5212
_diffrn_reflns_av_R_equivalents  0.037
# Number of reflections without Friedels Law is 5212 
# Number of reflections with Friedels Law is 3041 
# Theoretical number of reflections is about 3068 


_diffrn_reflns_theta_min         3.623
_diffrn_reflns_theta_max         70.065
_diffrn_measured_fraction_theta_max 0.971

_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_full 0.986


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              -16
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_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         -0.30
_refine_diff_density_max         1.14


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


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     51
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5188
_oxford_refine_ls_R_factor_ref   0.0546
_refine_ls_wR_factor_ref         0.1315
_refine_ls_goodness_of_fit_ref   0.8964
_refine_ls_shift/su_max          0.0001910
_refine_ls_shift/su_mean         0.0000232


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5188
_refine_ls_R_factor_all          0.0546
_refine_ls_wR_factor_all         0.1315

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4746
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_gt          0.1272

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661\"i?1/2683 
_oxford_Hooft_y                  0.081(10) # for 2041 Friedel pairs 
_oxford_Bijvoet_difference       0.074(11) # for 2041 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.039(16) # for 2171 Friedel pairs 
_refine_ls_abs_structure_Flack   0.074(11)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 2041 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 8.25 12.5 5.76 1.34 
;

# 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 -0.07815(11) 0.88607(8) 0.09922(6) 0.0386 1.0000 Uani . . . . . .
Cl2 Cl 0.09216(9) 0.61300(8) 0.41858(6) 0.0365 1.0000 Uani . . . . . .
O3 O 0.7747(3) 0.52589(19) 0.3971(2) 0.0389 1.0000 Uani D . . . . .
C4 C 0.7055(4) 0.4992(3) 0.2868(3) 0.0341 1.0000 Uani . . . . . .
C5 C 0.5572(4) 0.5532(2) 0.2362(3) 0.0276 1.0000 Uani D . . . . .
N6 N 0.5813(3) 0.65053(19) 0.2210(2) 0.0256 1.0000 Uani D . . . . .
C7 C 0.6387(4) 0.6711(2) 0.1260(3) 0.0307 1.0000 Uani D . . . . .
C8 C 0.5088(4) 0.6817(2) 0.0211(3) 0.0299 1.0000 Uani D . . . . .
N9 N 0.4140(3) 0.7609(2) 0.0327(2) 0.0306 1.0000 Uani D . . . . .
C10 C 0.2601(4) 0.7651(2) -0.0436(3) 0.0325 1.0000 Uani D . . . . .
C11 C 0.1452(4) 0.6912(2) -0.0305(3) 0.0279 1.0000 Uani D . . . . .
N12 N 0.1324(3) 0.6949(2) 0.0822(2) 0.0276 1.0000 Uani D . . . . .
C13 C 0.0647(3) 0.6126(3) 0.1144(2) 0.0287 1.0000 Uani D . . . . .
C14 C 0.1894(4) 0.5431(2) 0.1636(2) 0.0246 1.0000 Uani D . . . . .
N15 N 0.2994(3) 0.58959(18) 0.2591(2) 0.0236 1.0000 Uani D . . . . .
C16 C 0.4496(4) 0.5427(2) 0.3090(3) 0.0273 1.0000 Uani D . . . . .
C17 C 0.1248(4) 0.4559(2) 0.1981(3) 0.0346 1.0000 Uani . . . . . .
C18 C -0.0103(4) 0.7028(3) -0.1167(3) 0.0343 1.0000 Uani . . . . . .
C19 C 0.5782(4) 0.6946(3) -0.0749(3) 0.0382 1.0000 Uani . . . . . .
O20 O 0.4181(4) 0.6650(3) 0.5932(3) 0.0750 1.0000 Uani D . . . . .
C21 C 0.4627(6) 0.7590(4) 0.5985(4) 0.0619 1.0000 Uani . . . . . .
C22 C 0.5477(4) 0.7862(3) 0.5142(3) 0.0363 1.0000 Uani D . . . . .
N23 N 0.4493(3) 0.7742(2) 0.4031(2) 0.0328 1.0000 Uani D . . . . .
C24 C 0.3374(4) 0.8480(3) 0.3632(4) 0.0457 1.0000 Uani D . . . . .
C25 C 0.4045(4) 0.9378(3) 0.3377(4) 0.0430 1.0000 Uani D . . . . .
N26 N 0.4886(4) 0.9208(2) 0.2554(3) 0.0398 1.0000 Uani D . . . . .
C27 C 0.5852(5) 0.9967(3) 0.2389(3) 0.0399 1.0000 Uani D . . . . .
C28 C 0.7460(4) 0.9924(2) 0.3173(3) 0.0303 1.0000 Uani D . . . . .
N29 N 0.8085(3) 0.89849(19) 0.3073(2) 0.0267 1.0000 Uani D . . . . .
C30 C 0.9406(4) 0.8678(2) 0.3998(3) 0.0278 1.0000 Uani D . . . . .
C31 C 0.8857(4) 0.8339(2) 0.4952(3) 0.0249 1.0000 Uani D . . . . .
N32 N 0.7839(3) 0.75517(18) 0.4576(2) 0.0243 1.0000 Uani D . . . . .
C33 C 0.6913(4) 0.7285(3) 0.5313(3) 0.0320 1.0000 Uani D . . . . .
C34 C 1.0254(4) 0.8131(3) 0.5924(3) 0.0327 1.0000 Uani . . . . . .
C35 C 0.8525(6) 1.0648(2) 0.2948(3) 0.0420 1.0000 Uani . . . . . .
C36 C 0.2756(5) 1.0096(3) 0.3041(6) 0.0728 1.0000 Uani . . . . . .
O37 O 0.5641(4) 0.9235(2) -0.0190(3) 0.0552 1.0000 Uani D . . . . .
H41 H 0.7756 0.5102 0.2432 0.0425 1.0000 Uiso R . . . . .
H42 H 0.6795 0.4341 0.2840 0.0421 1.0000 Uiso R . . . . .
H51 H 0.5075 0.5270 0.1657 0.0331 1.0000 Uiso R . . . . .
H71 H 0.6953 0.7294 0.1392 0.0380 1.0000 Uiso R . . . . .
H72 H 0.7064 0.6218 0.1157 0.0379 1.0000 Uiso R . . . . .
H81 H 0.4461 0.6252 0.0089 0.0364 1.0000 Uiso R . . . . .
H101 H 0.2163 0.8238 -0.0364 0.0393 1.0000 Uiso R . . . . .
H102 H 0.2701 0.7596 -0.1173 0.0391 1.0000 Uiso R . . . . .
H111 H 0.1867 0.6308 -0.0399 0.0335 1.0000 Uiso R . . . . .
H132 H 0.0162 0.6289 0.1705 0.0359 1.0000 Uiso R . . . . .
H131 H -0.0120 0.5850 0.0529 0.0356 1.0000 Uiso R . . . . .
H141 H 0.2406 0.5281 0.1097 0.0292 1.0000 Uiso R . . . . .
H161 H 0.4936 0.5726 0.3788 0.0341 1.0000 Uiso R . . . . .
H162 H 0.4297 0.4789 0.3215 0.0341 1.0000 Uiso R . . . . .
H173 H 0.2036 0.4102 0.2190 0.0535 1.0000 Uiso R . . . . .
H172 H 0.0834 0.4669 0.2582 0.0528 1.0000 Uiso R . . . . .
H171 H 0.0457 0.4327 0.1380 0.0529 1.0000 Uiso R . . . . .
H183 H -0.0797 0.6555 -0.1097 0.0525 1.0000 Uiso R . . . . .
H181 H -0.0586 0.7611 -0.1096 0.0528 1.0000 Uiso R . . . . .
H182 H 0.0004 0.6986 -0.1902 0.0534 1.0000 Uiso R . . . . .
H192 H 0.4974 0.7029 -0.1429 0.0574 1.0000 Uiso R . . . . .
H193 H 0.6449 0.7461 -0.0643 0.0577 1.0000 Uiso R . . . . .
H191 H 0.6356 0.6416 -0.0828 0.0573 1.0000 Uiso R . . . . .
H212 H 0.5296 0.7735 0.6711 0.0752 1.0000 Uiso R . . . . .
H211 H 0.3687 0.7952 0.5810 0.0747 1.0000 Uiso R . . . . .
H221 H 0.5815 0.8497 0.5277 0.0448 1.0000 Uiso R . . . . .
H242 H 0.2888 0.8601 0.4218 0.0558 1.0000 Uiso R . . . . .
H241 H 0.2617 0.8277 0.2958 0.0566 1.0000 Uiso R . . . . .
H251 H 0.4788 0.9604 0.4040 0.0515 1.0000 Uiso R . . . . .
H272 H 0.5433 1.0558 0.2487 0.0495 1.0000 Uiso R . . . . .
H271 H 0.5965 0.9906 0.1677 0.0489 1.0000 Uiso R . . . . .
H281 H 0.7394 0.9997 0.3913 0.0361 1.0000 Uiso R . . . . .
H302 H 1.0121 0.9157 0.4231 0.0341 1.0000 Uiso R . . . . .
H301 H 0.9909 0.8162 0.3729 0.0327 1.0000 Uiso R . . . . .
H311 H 0.8249 0.8806 0.5179 0.0304 1.0000 Uiso R . . . . .
H332 H 0.7514 0.7322 0.6058 0.0388 1.0000 Uiso R . . . . .
H331 H 0.6620 0.6663 0.5154 0.0381 1.0000 Uiso R . . . . .
H341 H 0.9899 0.8016 0.6552 0.0509 1.0000 Uiso R . . . . .
H343 H 1.0893 0.8655 0.6057 0.0506 1.0000 Uiso R . . . . .
H342 H 1.0812 0.7616 0.5785 0.0502 1.0000 Uiso R . . . . .
H352 H 0.9444 1.0683 0.3535 0.0637 1.0000 Uiso R . . . . .
H351 H 0.8028 1.1236 0.2863 0.0632 1.0000 Uiso R . . . . .
H353 H 0.8782 1.0503 0.2286 0.0633 1.0000 Uiso R . . . . .
H362 H 0.3214 1.0675 0.2999 0.1079 1.0000 Uiso R . . . . .
H363 H 0.2184 1.0143 0.3578 0.1081 1.0000 Uiso R . . . . .
H361 H 0.2066 0.9956 0.2304 0.1078 1.0000 Uiso R . . . . .
H291 H 0.733(2) 0.8572(14) 0.297(2) 0.040(2) 1.0000 Uiso D . . . . .
H152 H 0.254(2) 0.6005(18) 0.3108(16) 0.036(2) 1.0000 Uiso D . . . . .
H321 H 0.844(3) 0.7096(13) 0.455(2) 0.029(2) 1.0000 Uiso D . . . . .
H151 H 0.318(3) 0.6461(14) 0.2405(19) 0.035(2) 1.0000 Uiso D . . . . .
H91 H 0.401(3) 0.754(2) 0.0976(16) 0.037(2) 1.0000 Uiso D . . . . .
H121 H 0.072(3) 0.7399(15) 0.083(2) 0.035(2) 1.0000 Uiso D . . . . .
H292 H 0.832(3) 0.8952(17) 0.2443(16) 0.040(2) 1.0000 Uiso D . . . . .
H61 H 0.650(3) 0.6695(17) 0.2789(16) 0.031(2) 1.0000 Uiso D . . . . .
H371 H 0.523(7) 0.878(3) -0.001(5) 0.085(2) 1.0000 Uiso D . . . . .
H261 H 0.431(3) 0.902(2) 0.1955(16) 0.049(2) 1.0000 Uiso D . . . . .
H231 H 0.505(3) 0.772(2) 0.3595(17) 0.041(2) 1.0000 Uiso D . . . . .
H31 H 0.862(3) 0.543(4) 0.403(4) 0.058(2) 1.0000 Uiso D . . . . .
H201 H 0.356(8) 0.669(6) 0.529(3) 0.115(2) 1.0000 Uiso D . . . . .
H373 H 0.656(3) 0.908(5) 0.011(5) 0.085(2) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.18363(15)
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
O3 . C4 . 1.419(4) yes
O3 . H31 . 0.814(19) no
C4 . C5 . 1.531(5) yes
C4 . H41 . 0.966 no
C4 . H42 . 0.982 no
C5 . N6 . 1.463(4) yes
C5 . C16 . 1.528(5) yes
C5 . H51 . 0.962 no
N6 . C7 . 1.475(4) yes
N6 . H61 . 0.864(18) no
C7 . C8 . 1.514(5) yes
C7 . H71 . 0.985 no
C7 . H72 . 0.979 no
C8 . N9 . 1.473(5) yes
C8 . C19 . 1.533(5) yes
C8 . H81 . 0.990 no
N9 . C10 . 1.454(4) yes
N9 . H91 . 0.874(18) no
C10 . C11 . 1.542(5) yes
C10 . H101 . 0.962 no
C10 . H102 . 0.970 no
C11 . N12 . 1.472(4) yes
C11 . C18 . 1.526(5) yes
C11 . H111 . 0.982 no
N12 . C13 . 1.461(4) yes
N12 . H121 . 0.860(18) no
C13 . C14 . 1.516(5) yes
C13 . H132 . 0.966 no
C13 . H131 . 0.974 no
C14 . N15 . 1.498(4) yes
C14 . C17 . 1.518(5) yes
C14 . H141 . 0.955 no
N15 . C16 . 1.492(4) yes
N15 . H152 . 0.880(18) no
N15 . H151 . 0.891(18) no
C16 . H161 . 0.968 no
C16 . H162 . 0.973 no
C17 . H173 . 0.958 no
C17 . H172 . 0.955 no
C17 . H171 . 0.949 no
C18 . H183 . 0.955 no
C18 . H181 . 0.975 no
C18 . H182 . 0.968 no
C19 . H192 . 0.968 no
C19 . H193 . 0.951 no
C19 . H191 . 0.955 no
O20 . C21 . 1.431(7) yes
O20 . H201 . 0.856(19) no
C21 . C22 . 1.537(5) yes
C21 . H212 . 0.974 no
C21 . H211 . 0.972 no
C22 . N23 . 1.451(5) yes
C22 . C33 . 1.512(5) yes
C22 . H221 . 0.979 no
N23 . C24 . 1.469(5) yes
N23 . H231 . 0.851(18) no
C24 . C25 . 1.521(6) yes
C24 . H242 . 0.983 no
C24 . H241 . 0.979 no
C25 . N26 . 1.477(5) yes
C25 . C36 . 1.537(6) yes
C25 . H251 . 0.975 no
N26 . C27 . 1.464(5) yes
N26 . H261 . 0.841(19) no
C27 . C28 . 1.512(5) yes
C27 . H272 . 0.967 no
C27 . H271 . 0.943 no
C28 . N29 . 1.505(4) yes
C28 . C35 . 1.513(5) yes
C28 . H281 . 0.965 no
N29 . C30 . 1.488(4) yes
N29 . H291 . 0.895(18) no
N29 . H292 . 0.888(18) no
C30 . C31 . 1.518(4) yes
C30 . H302 . 0.943 no
C30 . H301 . 0.990 no
C31 . N32 . 1.468(4) yes
C31 . C34 . 1.526(4) yes
C31 . H311 . 0.971 no
N32 . C33 . 1.475(4) yes
N32 . H321 . 0.866(18) no
C33 . H332 . 0.951 no
C33 . H331 . 0.955 no
C34 . H341 . 0.957 no
C34 . H343 . 0.946 no
C34 . H342 . 0.952 no
C35 . H352 . 0.947 no
C35 . H351 . 0.963 no
C35 . H353 . 0.958 no
C36 . H362 . 0.951 no
C36 . H363 . 0.969 no
C36 . H361 . 0.988 no
O37 . H371 . 0.826(19) no
O37 . H373 . 0.835(19) 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
C4 . O3 . H31 . 109(4) no
O3 . C4 . C5 . 111.2(3) yes
O3 . C4 . H41 . 110.2 no
C5 . C4 . H41 . 108.1 no
O3 . C4 . H42 . 109.7 no
C5 . C4 . H42 . 108.4 no
H41 . C4 . H42 . 109.3 no
C4 . C5 . N6 . 114.4(3) yes
C4 . C5 . C16 . 108.9(3) yes
N6 . C5 . C16 . 108.8(3) yes
C4 . C5 . H51 . 107.9 no
N6 . C5 . H51 . 108.2 no
C16 . C5 . H51 . 108.4 no
C5 . N6 . C7 . 114.0(2) yes
C5 . N6 . H61 . 107.4(15) no
C7 . N6 . H61 . 107.2(15) no
N6 . C7 . C8 . 112.2(3) yes
N6 . C7 . H71 . 108.8 no
C8 . C7 . H71 . 107.3 no
N6 . C7 . H72 . 109.7 no
C8 . C7 . H72 . 108.4 no
H71 . C7 . H72 . 110.4 no
C7 . C8 . N9 . 108.7(3) yes
C7 . C8 . C19 . 109.0(3) yes
N9 . C8 . C19 . 111.3(3) yes
C7 . C8 . H81 . 108.5 no
N9 . C8 . H81 . 110.6 no
C19 . C8 . H81 . 108.8 no
C8 . N9 . C10 . 116.1(3) yes
C8 . N9 . H91 . 103.9(16) no
C10 . N9 . H91 . 105.9(16) no
N9 . C10 . C11 . 116.3(3) yes
N9 . C10 . H101 . 108.4 no
C11 . C10 . H101 . 108.1 no
N9 . C10 . H102 . 108.0 no
C11 . C10 . H102 . 107.2 no
H101 . C10 . H102 . 108.7 no
C10 . C11 . N12 . 108.7(3) yes
C10 . C11 . C18 . 110.8(3) yes
N12 . C11 . C18 . 112.7(3) yes
C10 . C11 . H111 . 109.1 no
N12 . C11 . H111 . 106.9 no
C18 . C11 . H111 . 108.5 no
C11 . N12 . C13 . 113.3(3) yes
C11 . N12 . H121 . 105.7(15) no
C13 . N12 . H121 . 107.9(16) no
N12 . C13 . C14 . 110.5(2) yes
N12 . C13 . H132 . 108.4 no
C14 . C13 . H132 . 107.5 no
N12 . C13 . H131 . 112.1 no
C14 . C13 . H131 . 109.2 no
H132 . C13 . H131 . 109.1 no
C13 . C14 . N15 . 105.9(3) yes
C13 . C14 . C17 . 112.5(3) yes
N15 . C14 . C17 . 111.6(3) yes
C13 . C14 . H141 . 108.2 no
N15 . C14 . H141 . 110.0 no
C17 . C14 . H141 . 108.5 no
C14 . N15 . C16 . 116.7(2) yes
C14 . N15 . H152 . 110.4(14) no
C16 . N15 . H152 . 108.8(14) no
C14 . N15 . H151 . 109.9(14) no
C16 . N15 . H151 . 108.7(14) no
H152 . N15 . H151 . 101.2(17) no
C5 . C16 . N15 . 110.7(2) yes
C5 . C16 . H161 . 110.1 no
N15 . C16 . H161 . 105.7 no
C5 . C16 . H162 . 112.0 no
N15 . C16 . H162 . 108.9 no
H161 . C16 . H162 . 109.4 no
C14 . C17 . H173 . 110.6 no
C14 . C17 . H172 . 111.0 no
H173 . C17 . H172 . 108.8 no
C14 . C17 . H171 . 109.4 no
H173 . C17 . H171 . 107.7 no
H172 . C17 . H171 . 109.2 no
C11 . C18 . H183 . 110.3 no
C11 . C18 . H181 . 112.0 no
H183 . C18 . H181 . 107.7 no
C11 . C18 . H182 . 111.4 no
H183 . C18 . H182 . 106.9 no
H181 . C18 . H182 . 108.3 no
C8 . C19 . H192 . 110.7 no
C8 . C19 . H193 . 111.7 no
H192 . C19 . H193 . 108.2 no
C8 . C19 . H191 . 110.0 no
H192 . C19 . H191 . 107.6 no
H193 . C19 . H191 . 108.6 no
C21 . O20 . H201 . 94(6) no
O20 . C21 . C22 . 114.0(4) yes
O20 . C21 . H212 . 110.2 no
C22 . C21 . H212 . 107.9 no
O20 . C21 . H211 . 107.4 no
C22 . C21 . H211 . 105.9 no
H212 . C21 . H211 . 111.4 no
C21 . C22 . N23 . 111.0(3) yes
C21 . C22 . C33 . 109.4(4) yes
N23 . C22 . C33 . 109.7(3) yes
C21 . C22 . H221 . 108.5 no
N23 . C22 . H221 . 111.2 no
C33 . C22 . H221 . 107.0 no
C22 . N23 . C24 . 114.8(3) yes
C22 . N23 . H231 . 109.1(16) no
C24 . N23 . H231 . 106.7(16) no
N23 . C24 . C25 . 115.7(3) yes
N23 . C24 . H242 . 106.3 no
C25 . C24 . H242 . 107.2 no
N23 . C24 . H241 . 108.7 no
C25 . C24 . H241 . 107.4 no
H242 . C24 . H241 . 111.6 no
C24 . C25 . N26 . 108.7(3) yes
C24 . C25 . C36 . 109.6(3) yes
N26 . C25 . C36 . 114.7(4) yes
C24 . C25 . H251 . 109.1 no
N26 . C25 . H251 . 107.7 no
C36 . C25 . H251 . 106.8 no
C25 . N26 . C27 . 114.9(3) yes
C25 . N26 . H261 . 112.9(16) no
C27 . N26 . H261 . 111.5(16) no
N26 . C27 . C28 . 111.9(3) yes
N26 . C27 . H272 . 112.9 no
C28 . C27 . H272 . 106.9 no
N26 . C27 . H271 . 107.2 no
C28 . C27 . H271 . 106.5 no
H272 . C27 . H271 . 111.2 no
C27 . C28 . N29 . 107.2(3) yes
C27 . C28 . C35 . 112.9(3) yes
N29 . C28 . C35 . 110.5(3) yes
C27 . C28 . H281 . 109.0 no
N29 . C28 . H281 . 108.2 no
C35 . C28 . H281 . 108.9 no
C28 . N29 . C30 . 116.4(3) yes
C28 . N29 . H291 . 109.8(15) no
C30 . N29 . H291 . 108.6(14) no
C28 . N29 . H292 . 108.5(15) no
C30 . N29 . H292 . 110.6(14) no
H291 . N29 . H292 . 101.8(17) no
N29 . C30 . C31 . 111.1(3) yes
N29 . C30 . H302 . 110.4 no
C31 . C30 . H302 . 110.0 no
N29 . C30 . H301 . 107.5 no
C31 . C30 . H301 . 108.2 no
H302 . C30 . H301 . 109.6 no
C30 . C31 . N32 . 108.2(2) yes
C30 . C31 . C34 . 109.3(3) yes
N32 . C31 . C34 . 113.9(3) yes
C30 . C31 . H311 . 110.4 no
N32 . C31 . H311 . 107.2 no
C34 . C31 . H311 . 107.9 no
C31 . N32 . C33 . 114.6(2) yes
C31 . N32 . H321 . 106.1(15) no
C33 . N32 . H321 . 107.1(15) no
C22 . C33 . N32 . 112.2(3) yes
C22 . C33 . H332 . 109.6 no
N32 . C33 . H332 . 110.6 no
C22 . C33 . H331 . 109.1 no
N32 . C33 . H331 . 106.9 no
H332 . C33 . H331 . 108.2 no
C31 . C34 . H341 . 108.4 no
C31 . C34 . H343 . 107.8 no
H341 . C34 . H343 . 109.0 no
C31 . C34 . H342 . 111.6 no
H341 . C34 . H342 . 109.5 no
H343 . C34 . H342 . 110.4 no
C28 . C35 . H352 . 110.5 no
C28 . C35 . H351 . 110.3 no
H352 . C35 . H351 . 108.5 no
C28 . C35 . H353 . 109.6 no
H352 . C35 . H353 . 109.2 no
H351 . C35 . H353 . 108.7 no
C25 . C36 . H362 . 108.6 no
C25 . C36 . H363 . 111.4 no
H362 . C36 . H363 . 107.7 no
C25 . C36 . H361 . 110.3 no
H362 . C36 . H361 . 107.4 no
H363 . C36 . H361 . 111.4 no
H371 . O37 . H373 . 97(6) 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 . O37 2_645 162 0.96 2.35 3.275(5) yes
C27 . H272 . O20 2_656 135 0.97 2.52 3.266(5) yes
C27 . H271 . O37 . 158 0.94 2.51 3.405(5) yes
N6 . H61 . N32 . 162(3) 0.864 2.577 3.411(5) yes
O37 . H371 . N9 . 176(7) 0.826 2.082 2.906(5) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
