# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6ad
_database_code_depnum_ccdc_archive 'CCDC 1513617'
_audit_update_record             
;
2016-10-31 deposited with the CCDC.
2017-02-08 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          
; 
? 
;
_cell_length_a                   15.6516(5)
_cell_length_b                   14.7041(4)
_cell_length_c                   20.8303(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4793.9(2)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  '-P 2ac 2ab '
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
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 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'
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'
Cl 0.1484 0.1585 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'
Br -0.2901 2.4595 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'
P 0.1023 0.0942 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'
Si 0.0817 0.0704 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8


_chemical_formula_sum            'C23 H30 N4 O2 Si1'
_chemical_formula_moiety         'C23 H30 N4 O2 Si1'
_chemical_compound_source        ?
_chemical_formula_weight         422.60


_cell_measurement_reflns_used    101
_cell_measurement_theta_min      2
_cell_measurement_theta_max      21
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.096
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_max          0.291

_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1808
_exptl_absorpt_coefficient_mu    0.123

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex3'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ scans'

_computing_data_collection       'Apex3 (Bruker AXS, 2015)'
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_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      180
_diffrn_ambient_pressure         101
_diffrn_reflns_number            33307
_reflns_number_total             4920
_diffrn_reflns_av_R_equivalents  0.028


_diffrn_reflns_theta_min         1.955
_diffrn_reflns_theta_max         26.410
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        26.410
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_reflns_limit_h_min              0
_reflns_limit_h_max              19
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              26

_oxford_diffrn_Wilson_B_factor   2.70
_oxford_diffrn_Wilson_scale      233.93

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.27
_refine_diff_density_max         0.29


_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4899
_refine_ls_number_restraints     0
_refine_ls_number_parameters     271
_oxford_refine_ls_R_factor_ref   0.0464
_refine_ls_wR_factor_ref         0.1005
_refine_ls_goodness_of_fit_ref   1.0233
_refine_ls_shift/su_max          0.0009782
_refine_ls_shift/su_mean         0.0000784

_oxford_reflns_number_all        4914
_refine_ls_R_factor_all          0.0480
_refine_ls_wR_factor_all         0.1007

_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4290
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_gt          0.0942

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_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: 
 5.49 8.37 3.96 0.980 
;


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 0.50897(7) 0.88106(8) 0.60134(5) 0.0258 1.0000 Uani . . . . . .
N2 N 0.48122(8) 0.88862(8) 0.53937(6) 0.0311 1.0000 Uani . . . . . .
N3 N 0.41942(8) 0.83054(8) 0.53219(6) 0.0309 1.0000 Uani . . . . . .
C4 C 0.40496(9) 0.78352(9) 0.58869(6) 0.0258 1.0000 Uani . . . . . .
C5 C 0.46318(9) 0.81596(9) 0.63324(6) 0.0245 1.0000 Uani . . . . . .
C6 C 0.58293(9) 0.93257(9) 0.61840(6) 0.0255 1.0000 Uani . . . . . .
C7 C 0.59127(10) 1.01884(10) 0.59204(7) 0.0312 1.0000 Uani . . . . . .
C8 C 0.66564(10) 1.06740(10) 0.60181(7) 0.0336 1.0000 Uani . . . . . .
C9 C 0.72978(9) 1.02882(10) 0.63857(6) 0.0298 1.0000 Uani . . . . . .
C10 C 0.72175(9) 0.94357(10) 0.66604(7) 0.0324 1.0000 Uani . . . . . .
C11 C 0.64732(9) 0.89478(10) 0.65586(7) 0.0311 1.0000 Uani . . . . . .
N12 N 0.81070(9) 1.07873(9) 0.64670(6) 0.0371 1.0000 Uani . . . . . .
O13 O 0.81516(10) 1.15606(10) 0.62516(8) 0.0643 1.0000 Uani . . . . . .
O14 O 0.86935(7) 1.04104(8) 0.67459(6) 0.0456 1.0000 Uani . . . . . .
C15 C 0.47361(8) 0.79599(9) 0.70239(6) 0.0249 1.0000 Uani . . . . . .
C16 C 0.46141(10) 0.86390(10) 0.74818(7) 0.0344 1.0000 Uani . . . . . .
C17 C 0.46537(11) 0.84320(12) 0.81316(8) 0.0420 1.0000 Uani . . . . . .
C18 C 0.48056(11) 0.75481(13) 0.83297(7) 0.0414 1.0000 Uani . . . . . .
C19 C 0.49367(11) 0.68770(11) 0.78780(8) 0.0388 1.0000 Uani . . . . . .
C20 C 0.49098(9) 0.70777(10) 0.72267(7) 0.0307 1.0000 Uani . . . . . .
Si21 Si 0.31442(2) 0.69908(2) 0.586836(17) 0.0246 1.0000 Uani . . . . . .
C22 C 0.23202(10) 0.75485(10) 0.53334(8) 0.0354 1.0000 Uani . . . . . .
C23 C 0.20423(14) 0.84987(13) 0.55403(12) 0.0628 1.0000 Uani . . . . . .
C24 C 0.15408(12) 0.69654(14) 0.51881(10) 0.0528 1.0000 Uani . . . . . .
C25 C 0.35416(9) 0.59293(10) 0.54558(7) 0.0310 1.0000 Uani . . . . . .
C26 C 0.38073(13) 0.60873(13) 0.47590(8) 0.0472 1.0000 Uani . . . . . .
C27 C 0.42755(11) 0.54797(11) 0.58265(9) 0.0435 1.0000 Uani . . . . . .
C28 C 0.27818(10) 0.66831(12) 0.67043(7) 0.0379 1.0000 Uani . . . . . .
C29 C 0.24085(14) 0.74816(15) 0.70840(9) 0.0586 1.0000 Uani . . . . . .
C30 C 0.21637(13) 0.58705(14) 0.67041(9) 0.0535 1.0000 Uani . . . . . .
H71 H 0.5461 1.0443 0.5675 0.0378 1.0000 Uiso R . . . . .
H81 H 0.6726 1.1262 0.5837 0.0404 1.0000 Uiso R . . . . .
H101 H 0.7665 0.9190 0.6915 0.0391 1.0000 Uiso R . . . . .
H111 H 0.6403 0.8362 0.6743 0.0376 1.0000 Uiso R . . . . .
H161 H 0.4505 0.9246 0.7349 0.0416 1.0000 Uiso R . . . . .
H171 H 0.4576 0.8899 0.8441 0.0508 1.0000 Uiso R . . . . .
H181 H 0.4818 0.7404 0.8774 0.0498 1.0000 Uiso R . . . . .
H191 H 0.5048 0.6271 0.8013 0.0467 1.0000 Uiso R . . . . .
H201 H 0.5010 0.6612 0.6920 0.0369 1.0000 Uiso R . . . . .
H221 H 0.2597 0.7630 0.4932 0.0426 1.0000 Uiso R . . . . .
H231 H 0.1630 0.8726 0.5247 0.0756 1.0000 Uiso R . . . . .
H232 H 0.2525 0.8891 0.5546 0.0756 1.0000 Uiso R . . . . .
H233 H 0.1800 0.8471 0.5958 0.0756 1.0000 Uiso R . . . . .
H241 H 0.1161 0.7293 0.4918 0.0635 1.0000 Uiso R . . . . .
H242 H 0.1259 0.6816 0.5578 0.0635 1.0000 Uiso R . . . . .
H243 H 0.1716 0.6423 0.4978 0.0635 1.0000 Uiso R . . . . .
H251 H 0.3081 0.5509 0.5450 0.0372 1.0000 Uiso R . . . . .
H261 H 0.4001 0.5531 0.4577 0.0569 1.0000 Uiso R . . . . .
H262 H 0.4255 0.6523 0.4745 0.0569 1.0000 Uiso R . . . . .
H263 H 0.3331 0.6306 0.4522 0.0569 1.0000 Uiso R . . . . .
H271 H 0.4457 0.4949 0.5605 0.0526 1.0000 Uiso R . . . . .
H272 H 0.4739 0.5894 0.5860 0.0526 1.0000 Uiso R . . . . .
H273 H 0.4085 0.5318 0.6244 0.0526 1.0000 Uiso R . . . . .
H281 H 0.3277 0.6492 0.6931 0.0457 1.0000 Uiso R . . . . .
H291 H 0.2240 0.7279 0.7498 0.0703 1.0000 Uiso R . . . . .
H292 H 0.2828 0.7945 0.7126 0.0703 1.0000 Uiso R . . . . .
H293 H 0.1925 0.7716 0.6863 0.0703 1.0000 Uiso R . . . . .
H301 H 0.1996 0.5737 0.7132 0.0641 1.0000 Uiso R . . . . .
H302 H 0.1673 0.6017 0.6457 0.0641 1.0000 Uiso R . . . . .
H303 H 0.2440 0.5356 0.6523 0.0641 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.11414(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 . N2 . 1.3665(15) yes
N1 . C5 . 1.3681(17) yes
N1 . C6 . 1.4283(17) yes
N2 . N3 . 1.2991(17) yes
N3 . C4 . 1.3836(18) yes
C4 . C5 . 1.3852(19) yes
C4 . Si21 . 1.8846(14) yes
C5 . C15 . 1.4791(18) yes
C6 . C7 . 1.3884(19) yes
C6 . C11 . 1.3903(19) yes
C7 . C8 . 1.381(2) yes
C7 . H71 . 0.950 no
C8 . C9 . 1.384(2) yes
C8 . H81 . 0.950 no
C9 . C10 . 1.384(2) yes
C9 . N12 . 1.4736(18) yes
C10 . C11 . 1.384(2) yes
C10 . H101 . 0.950 no
C11 . H111 . 0.950 no
N12 . O13 . 1.2244(19) yes
N12 . O14 . 1.2196(18) yes
C15 . C16 . 1.3940(19) yes
C15 . C20 . 1.3910(19) yes
C16 . C17 . 1.389(2) yes
C16 . H161 . 0.950 no
C17 . C18 . 1.384(3) yes
C17 . H171 . 0.950 no
C18 . C19 . 1.379(2) yes
C18 . H181 . 0.950 no
C19 . C20 . 1.389(2) yes
C19 . H191 . 0.950 no
C20 . H201 . 0.950 no
Si21 . C22 . 1.8913(16) yes
Si21 . C25 . 1.8873(14) yes
Si21 . C28 . 1.8864(16) yes
C22 . C23 . 1.525(2) yes
C22 . C24 . 1.521(2) yes
C22 . H221 . 0.950 no
C23 . H231 . 0.950 no
C23 . H232 . 0.950 no
C23 . H233 . 0.950 no
C24 . H241 . 0.950 no
C24 . H242 . 0.950 no
C24 . H243 . 0.950 no
C25 . C26 . 1.528(2) yes
C25 . C27 . 1.534(2) yes
C25 . H251 . 0.950 no
C26 . H261 . 0.950 no
C26 . H262 . 0.950 no
C26 . H263 . 0.950 no
C27 . H271 . 0.950 no
C27 . H272 . 0.950 no
C27 . H273 . 0.950 no
C28 . C29 . 1.532(2) yes
C28 . C30 . 1.537(2) yes
C28 . H281 . 0.950 no
C29 . H291 . 0.950 no
C29 . H292 . 0.950 no
C29 . H293 . 0.950 no
C30 . H301 . 0.950 no
C30 . H302 . 0.950 no
C30 . H303 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 . N1 . C5 . 110.44(11) yes
N2 . N1 . C6 . 116.71(11) yes
C5 . N1 . C6 . 132.44(11) yes
N1 . N2 . N3 . 106.98(11) yes
N2 . N3 . C4 . 110.63(11) yes
N3 . C4 . C5 . 106.87(12) yes
N3 . C4 . Si21 . 115.77(10) yes
C5 . C4 . Si21 . 137.32(10) yes
C4 . C5 . N1 . 105.08(11) yes
C4 . C5 . C15 . 131.05(12) yes
N1 . C5 . C15 . 123.64(12) yes
N1 . C6 . C7 . 117.53(12) yes
N1 . C6 . C11 . 121.00(12) yes
C7 . C6 . C11 . 121.27(13) yes
C6 . C7 . C8 . 119.56(13) yes
C6 . C7 . H71 . 120.2 no
C8 . C7 . H71 . 120.2 no
C7 . C8 . C9 . 118.76(13) yes
C7 . C8 . H81 . 120.6 no
C9 . C8 . H81 . 120.6 no
C8 . C9 . C10 . 122.28(13) yes
C8 . C9 . N12 . 118.88(13) yes
C10 . C9 . N12 . 118.80(13) yes
C9 . C10 . C11 . 118.85(13) yes
C9 . C10 . H101 . 120.5 no
C11 . C10 . H101 . 120.6 no
C6 . C11 . C10 . 119.26(13) yes
C6 . C11 . H111 . 120.4 no
C10 . C11 . H111 . 120.4 no
C9 . N12 . O13 . 118.00(14) yes
C9 . N12 . O14 . 118.39(13) yes
O13 . N12 . O14 . 123.62(14) yes
C5 . C15 . C16 . 120.60(12) yes
C5 . C15 . C20 . 120.16(12) yes
C16 . C15 . C20 . 119.14(13) yes
C15 . C16 . C17 . 120.25(14) yes
C15 . C16 . H161 . 119.9 no
C17 . C16 . H161 . 119.9 no
C16 . C17 . C18 . 120.27(15) yes
C16 . C17 . H171 . 119.8 no
C18 . C17 . H171 . 119.9 no
C17 . C18 . C19 . 119.60(14) yes
C17 . C18 . H181 . 120.2 no
C19 . C18 . H181 . 120.2 no
C18 . C19 . C20 . 120.66(15) yes
C18 . C19 . H191 . 119.7 no
C20 . C19 . H191 . 119.7 no
C15 . C20 . C19 . 120.04(14) yes
C15 . C20 . H201 . 120.0 no
C19 . C20 . H201 . 120.0 no
C4 . Si21 . C22 . 103.84(7) yes
C4 . Si21 . C25 . 107.84(6) yes
C22 . Si21 . C25 . 108.36(7) yes
C4 . Si21 . C28 . 111.42(6) yes
C22 . Si21 . C28 . 116.29(8) yes
C25 . Si21 . C28 . 108.73(7) yes
Si21 . C22 . C23 . 115.16(12) yes
Si21 . C22 . C24 . 114.81(12) yes
C23 . C22 . C24 . 110.10(15) yes
Si21 . C22 . H221 . 105.2 no
C23 . C22 . H221 . 105.2 no
C24 . C22 . H221 . 105.2 no
C22 . C23 . H231 . 109.5 no
C22 . C23 . H232 . 109.4 no
H231 . C23 . H232 . 109.5 no
C22 . C23 . H233 . 109.5 no
H231 . C23 . H233 . 109.5 no
H232 . C23 . H233 . 109.5 no
C22 . C24 . H241 . 109.5 no
C22 . C24 . H242 . 109.4 no
H241 . C24 . H242 . 109.5 no
C22 . C24 . H243 . 109.5 no
H241 . C24 . H243 . 109.5 no
H242 . C24 . H243 . 109.5 no
Si21 . C25 . C26 . 113.36(11) yes
Si21 . C25 . C27 . 111.97(10) yes
C26 . C25 . C27 . 109.87(13) yes
Si21 . C25 . H251 . 107.1 no
C26 . C25 . H251 . 107.1 no
C27 . C25 . H251 . 107.1 no
C25 . C26 . H261 . 109.5 no
C25 . C26 . H262 . 109.5 no
H261 . C26 . H262 . 109.5 no
C25 . C26 . H263 . 109.4 no
H261 . C26 . H263 . 109.5 no
H262 . C26 . H263 . 109.5 no
C25 . C27 . H271 . 109.5 no
C25 . C27 . H272 . 109.5 no
H271 . C27 . H272 . 109.5 no
C25 . C27 . H273 . 109.5 no
H271 . C27 . H273 . 109.5 no
H272 . C27 . H273 . 109.5 no
Si21 . C28 . C29 . 114.05(13) yes
Si21 . C28 . C30 . 112.04(11) yes
C29 . C28 . C30 . 110.85(14) yes
Si21 . C28 . H281 . 106.5 no
C29 . C28 . H281 . 106.4 no
C30 . C28 . H281 . 106.5 no
C28 . C29 . H291 . 109.5 no
C28 . C29 . H292 . 109.5 no
H291 . C29 . H292 . 109.5 no
C28 . C29 . H293 . 109.4 no
H291 . C29 . H293 . 109.5 no
H292 . C29 . H293 . 109.5 no
C28 . C30 . H301 . 109.5 no
C28 . C30 . H302 . 109.4 no
H301 . C30 . H302 . 109.5 no
C28 . C30 . H303 . 109.5 no
H301 . C30 . H303 . 109.5 no
H302 . C30 . H303 . 109.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 . H71 . N2 2_676 140 0.950 2.471 3.261(2) yes



loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
1 1 2 x .
1 1 1 x .
0 0 2 x .
0 2 0 x .
0 2 1 x .
1 0 2 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3ai
_database_code_depnum_ccdc_archive 'CCDC 1513614'
_audit_update_record             
;
2016-10-31 deposited with the CCDC.
2017-02-08 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          
; 
? 
;
_cell_length_a                   9.4684(3)
_cell_length_b                   10.4692(4)
_cell_length_c                   12.7710(4)
_cell_angle_alpha                96.2634(12)
_cell_angle_beta                 95.7478(12)
_cell_angle_gamma                113.6438(11)
_cell_volume                     1138.27(7)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2


_chemical_formula_sum            'C20 H21 N5 O2 Si1'
_chemical_formula_moiety         'C20 H21 N5 O2 Si1'
_chemical_compound_source        ?
_chemical_formula_weight         391.51


_cell_measurement_reflns_used    75
_cell_measurement_theta_min      4
_cell_measurement_theta_max      69
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.181
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_max          0.317

_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    1.099

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.82
_diffrn_measurement_device_type  'Bruker Kappa Apex3'
_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'

_computing_data_collection       'Apex3 (Bruker AXS, 2015)'
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_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      180
_diffrn_ambient_pressure         101
_diffrn_reflns_number            30145
_reflns_number_total             4161
_diffrn_reflns_av_R_equivalents  0.027


_diffrn_reflns_theta_min         3.526
_diffrn_reflns_theta_max         68.443
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        67.074
_diffrn_measured_fraction_theta_full 0.997


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

_oxford_diffrn_Wilson_B_factor   3.43
_oxford_diffrn_Wilson_scale      1.16

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.36
_refine_diff_density_max         0.29

_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_oxford_refine_ls_R_factor_ref   0.0524
_refine_ls_wR_factor_ref         0.1317
_refine_ls_goodness_of_fit_ref   1.0042
_refine_ls_shift/su_max          0.0002897
_refine_ls_shift/su_mean         0.0000152

_oxford_reflns_number_all        4161
_refine_ls_R_factor_all          0.0524
_refine_ls_wR_factor_all         0.1317

_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3808
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_gt          0.1269

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_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: 
 50.6 83.6 49.0 19.9 4.30 
;


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 0.46401(16) -0.00588(14) 0.19981(11) 0.0393 1.0000 Uani . . . . . .
N2 N 0.48451(19) -0.12364(15) 0.21886(12) 0.0472 1.0000 Uani . . . . . .
N3 N 0.59458(19) -0.08436(15) 0.30048(12) 0.0464 1.0000 Uani . . . . . .
C4 C 0.6474(2) 0.05789(17) 0.33725(14) 0.0408 1.0000 Uani . . . . . .
C5 C 0.56275(19) 0.10862(17) 0.27229(13) 0.0375 1.0000 Uani . . . . . .
C6 C 0.3519(2) -0.01900(19) 0.11129(13) 0.0408 1.0000 Uani . . . . . .
C7 C 0.3824(2) 0.0858(2) 0.04824(15) 0.0511 1.0000 Uani . . . . . .
C8 C 0.2747(3) 0.0689(2) -0.03895(16) 0.0561 1.0000 Uani . . . . . .
C9 C 0.1408(2) -0.0529(3) -0.06224(14) 0.0557 1.0000 Uani . . . . . .
C10 C 0.1073(3) -0.1565(3) 0.00004(18) 0.0662 1.0000 Uani . . . . . .
C11 C 0.2144(2) -0.1386(2) 0.08827(17) 0.0585 1.0000 Uani . . . . . .
N12 N 0.0269(3) -0.0722(3) -0.15611(15) 0.0734 1.0000 Uani . . . . . .
O13 O 0.0457(3) 0.0260(3) -0.20337(15) 0.1088 1.0000 Uani . . . . . .
O14 O -0.0811(2) -0.1884(3) -0.18362(16) 0.1050 1.0000 Uani . . . . . .
Si15 Si 0.79124(6) 0.14479(5) 0.46396(4) 0.0438 1.0000 Uani . . . . . .
C16 C 0.9923(3) 0.2376(3) 0.43723(18) 0.0682 1.0000 Uani . . . . . .
C17 C 0.7728(4) 0.0011(3) 0.5414(2) 0.0830 1.0000 Uani . . . . . .
C18 C 0.7325(3) 0.2740(3) 0.53687(19) 0.0723 1.0000 Uani . . . . . .
C19 C 0.56540(19) 0.25024(17) 0.27768(13) 0.0390 1.0000 Uani . . . . . .
C20 C 0.4497(2) 0.28902(19) 0.30297(16) 0.0473 1.0000 Uani . . . . . .
N21 N 0.49810(19) 0.43159(16) 0.30530(13) 0.0507 1.0000 Uani . . . . . .
C22 C 0.6469(2) 0.48795(18) 0.28117(14) 0.0437 1.0000 Uani . . . . . .
C23 C 0.7441(3) 0.62676(19) 0.27304(16) 0.0543 1.0000 Uani . . . . . .
C24 C 0.8884(3) 0.6508(2) 0.24599(18) 0.0621 1.0000 Uani . . . . . .
C25 C 0.9364(3) 0.5419(2) 0.22722(18) 0.0611 1.0000 Uani . . . . . .
C26 C 0.8410(2) 0.4049(2) 0.23487(16) 0.0495 1.0000 Uani . . . . . .
C27 C 0.6936(2) 0.37618(17) 0.26289(13) 0.0396 1.0000 Uani . . . . . .
C28 C 0.4115(3) 0.5133(3) 0.3379(2) 0.0747 1.0000 Uani . . . . . .
H71 H 0.4772 0.1688 0.0652 0.0618 1.0000 Uiso R . . . . .
H81 H 0.2931 0.1405 -0.0822 0.0678 1.0000 Uiso R . . . . .
H101 H 0.0121 -0.2391 -0.0171 0.0798 1.0000 Uiso R . . . . .
H111 H 0.1931 -0.2088 0.1329 0.0707 1.0000 Uiso R . . . . .
H161 H 1.0612 0.2799 0.5029 0.0830 1.0000 Uiso R . . . . .
H162 H 1.0225 0.1720 0.3993 0.0830 1.0000 Uiso R . . . . .
H163 H 0.9966 0.3088 0.3958 0.0830 1.0000 Uiso R . . . . .
H171 H 0.8433 0.0388 0.6068 0.1003 1.0000 Uiso R . . . . .
H172 H 0.7968 -0.0675 0.5014 0.1003 1.0000 Uiso R . . . . .
H173 H 0.6690 -0.0420 0.5558 0.1003 1.0000 Uiso R . . . . .
H181 H 0.8035 0.3193 0.6013 0.0876 1.0000 Uiso R . . . . .
H182 H 0.6303 0.2262 0.5529 0.0876 1.0000 Uiso R . . . . .
H183 H 0.7335 0.3427 0.4937 0.0876 1.0000 Uiso R . . . . .
H201 H 0.3509 0.2266 0.3169 0.0572 1.0000 Uiso R . . . . .
H231 H 0.7118 0.7013 0.2858 0.0658 1.0000 Uiso R . . . . .
H241 H 0.9573 0.7442 0.2399 0.0748 1.0000 Uiso R . . . . .
H251 H 1.0370 0.5625 0.2086 0.0737 1.0000 Uiso R . . . . .
H261 H 0.8746 0.3314 0.2216 0.0600 1.0000 Uiso R . . . . .
H281 H 0.4694 0.6097 0.3325 0.0904 1.0000 Uiso R . . . . .
H282 H 0.3954 0.5056 0.4096 0.0904 1.0000 Uiso R . . . . .
H283 H 0.3134 0.4778 0.2927 0.0904 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.992(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 . N2 . 1.3655(19) yes
N1 . C5 . 1.361(2) yes
N1 . C6 . 1.426(2) yes
N2 . N3 . 1.299(2) yes
N3 . C4 . 1.375(2) yes
C4 . C5 . 1.384(2) yes
C4 . Si15 . 1.8828(18) yes
C5 . C19 . 1.467(2) yes
C6 . C7 . 1.386(2) yes
C6 . C11 . 1.372(3) yes
C7 . C8 . 1.377(3) yes
C7 . H71 . 0.950 no
C8 . C9 . 1.366(3) yes
C8 . H81 . 0.950 no
C9 . C10 . 1.368(3) yes
C9 . N12 . 1.468(3) yes
C10 . C11 . 1.381(3) yes
C10 . H101 . 0.950 no
C11 . H111 . 0.950 no
N12 . O13 . 1.210(3) yes
N12 . O14 . 1.219(3) yes
Si15 . C16 . 1.845(2) yes
Si15 . C17 . 1.850(2) yes
Si15 . C18 . 1.854(2) yes
C16 . H161 . 0.950 no
C16 . H162 . 0.950 no
C16 . H163 . 0.950 no
C17 . H171 . 0.950 no
C17 . H172 . 0.950 no
C17 . H173 . 0.950 no
C18 . H181 . 0.950 no
C18 . H182 . 0.950 no
C18 . H183 . 0.950 no
C19 . C20 . 1.367(2) yes
C19 . C27 . 1.437(2) yes
C20 . N21 . 1.370(2) yes
C20 . H201 . 0.950 no
N21 . C22 . 1.374(2) yes
N21 . C28 . 1.460(2) yes
C22 . C23 . 1.396(3) yes
C22 . C27 . 1.412(2) yes
C23 . C24 . 1.373(3) yes
C23 . H231 . 0.950 no
C24 . C25 . 1.394(3) yes
C24 . H241 . 0.950 no
C25 . C26 . 1.375(3) yes
C25 . H251 . 0.950 no
C26 . C27 . 1.397(3) yes
C26 . H261 . 0.950 no
C28 . H281 . 0.950 no
C28 . H282 . 0.950 no
C28 . H283 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 . N1 . C5 . 110.48(14) yes
N2 . N1 . C6 . 118.42(14) yes
C5 . N1 . C6 . 131.08(14) yes
N1 . N2 . N3 . 106.91(13) yes
N2 . N3 . C4 . 110.53(13) yes
N3 . C4 . C5 . 107.09(15) yes
N3 . C4 . Si15 . 121.29(12) yes
C5 . C4 . Si15 . 131.20(13) yes
C4 . C5 . N1 . 104.99(14) yes
C4 . C5 . C19 . 130.51(16) yes
N1 . C5 . C19 . 124.44(15) yes
N1 . C6 . C7 . 120.61(16) yes
N1 . C6 . C11 . 118.83(16) yes
C7 . C6 . C11 . 120.55(18) yes
C6 . C7 . C8 . 119.68(19) yes
C6 . C7 . H71 . 120.1 no
C8 . C7 . H71 . 120.2 no
C7 . C8 . C9 . 118.78(19) yes
C7 . C8 . H81 . 120.6 no
C9 . C8 . H81 . 120.6 no
C8 . C9 . C10 . 122.41(19) yes
C8 . C9 . N12 . 118.9(2) yes
C10 . C9 . N12 . 118.6(2) yes
C9 . C10 . C11 . 118.7(2) yes
C9 . C10 . H101 . 120.6 no
C11 . C10 . H101 . 120.7 no
C10 . C11 . C6 . 119.80(19) yes
C10 . C11 . H111 . 120.1 no
C6 . C11 . H111 . 120.1 no
C9 . N12 . O13 . 119.0(2) yes
C9 . N12 . O14 . 117.8(2) yes
O13 . N12 . O14 . 123.2(2) yes
C4 . Si15 . C16 . 111.98(9) yes
C4 . Si15 . C17 . 105.67(10) yes
C16 . Si15 . C17 . 111.86(13) yes
C4 . Si15 . C18 . 107.93(9) yes
C16 . Si15 . C18 . 109.16(12) yes
C17 . Si15 . C18 . 110.12(14) yes
Si15 . C16 . H161 . 109.5 no
Si15 . C16 . H162 . 109.4 no
H161 . C16 . H162 . 109.5 no
Si15 . C16 . H163 . 109.5 no
H161 . C16 . H163 . 109.5 no
H162 . C16 . H163 . 109.5 no
Si15 . C17 . H171 . 109.5 no
Si15 . C17 . H172 . 109.4 no
H171 . C17 . H172 . 109.5 no
Si15 . C17 . H173 . 109.5 no
H171 . C17 . H173 . 109.5 no
H172 . C17 . H173 . 109.5 no
Si15 . C18 . H181 . 109.5 no
Si15 . C18 . H182 . 109.5 no
H181 . C18 . H182 . 109.5 no
Si15 . C18 . H183 . 109.4 no
H181 . C18 . H183 . 109.5 no
H182 . C18 . H183 . 109.5 no
C5 . C19 . C20 . 126.61(16) yes
C5 . C19 . C27 . 126.40(15) yes
C20 . C19 . C27 . 106.91(15) yes
C19 . C20 . N21 . 109.65(16) yes
C19 . C20 . H201 . 125.2 no
N21 . C20 . H201 . 125.2 no
C20 . N21 . C22 . 109.33(14) yes
C20 . N21 . C28 . 125.46(18) yes
C22 . N21 . C28 . 124.98(17) yes
N21 . C22 . C23 . 130.51(17) yes
N21 . C22 . C27 . 107.48(15) yes
C23 . C22 . C27 . 122.01(18) yes
C22 . C23 . C24 . 117.12(18) yes
C22 . C23 . H231 . 121.4 no
C24 . C23 . H231 . 121.5 no
C23 . C24 . C25 . 121.76(19) yes
C23 . C24 . H241 . 119.1 no
C25 . C24 . H241 . 119.1 no
C24 . C25 . C26 . 121.3(2) yes
C24 . C25 . H251 . 119.4 no
C26 . C25 . H251 . 119.3 no
C25 . C26 . C27 . 118.67(18) yes
C25 . C26 . H261 . 120.7 no
C27 . C26 . H261 . 120.6 no
C19 . C27 . C22 . 106.63(15) yes
C19 . C27 . C26 . 134.26(16) yes
C22 . C27 . C26 . 119.10(16) yes
N21 . C28 . H281 . 109.5 no
N21 . C28 . H282 . 109.5 no
H281 . C28 . H282 . 109.5 no
N21 . C28 . H283 . 109.4 no
H281 . C28 . H283 . 109.5 no
H282 . C28 . H283 . 109.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C24 . H241 . O13 2_665 141 0.950 2.510 3.303(3) yes


_iucr_refine_instruction_details_constraints 
;
BLOCK SCALE X'S, U'S 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) H   ( 163,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) H   ( 173,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) H   ( 283,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# 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_3ia
_database_code_depnum_ccdc_archive 'CCDC 1513616'
_audit_update_record             
;
2016-10-31 deposited with the CCDC.
2017-02-08 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          
; 
? 
;
_cell_length_a                   16.2913(7)
_cell_length_b                   10.0932(4)
_cell_length_c                   19.7897(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.8945(12)
_cell_angle_gamma                90
_cell_volume                     2997.7(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_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'
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'
Br -0.2901 2.4595 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'


_cell_formula_units_Z            8


_chemical_formula_sum            'C14 H8 Br3 N3'
_chemical_formula_moiety         'C14 H8 Br3 N3'
_chemical_compound_source        ?
_chemical_formula_weight         457.95


_cell_measurement_reflns_used    547
_cell_measurement_theta_min      2
_cell_measurement_theta_max      22
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.308
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_max          0.581

_exptl_crystal_density_diffrn    2.029
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    8.066

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.03
_exptl_absorpt_correction_T_max  0.08
_diffrn_measurement_device_type  'Bruker Kappa Apex3'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

_computing_data_collection       'Apex3 (Bruker AXS, 2015)'
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_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      180
_diffrn_reflns_number            41005
_reflns_number_total             6137
_diffrn_reflns_av_R_equivalents  0.088


_diffrn_reflns_theta_min         2.066
_diffrn_reflns_theta_max         26.415
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        26.415
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -20
_reflns_limit_h_max              18
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   2.19
_oxford_diffrn_Wilson_scale      184.84

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.48
_refine_diff_density_max         1.57

_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         6136
_refine_ls_number_restraints     0
_refine_ls_number_parameters     362
_oxford_refine_ls_R_factor_ref   0.0659
_refine_ls_wR_factor_ref         0.0956
_refine_ls_goodness_of_fit_ref   0.9177
_refine_ls_shift/su_max          0.0007551
_refine_ls_shift/su_mean         0.0000296

_oxford_reflns_number_all        6136
_refine_ls_R_factor_all          0.0659
_refine_ls_wR_factor_all         0.0956

_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4474
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_gt          0.0746

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_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: 
 3.07 3.51 1.00 
;


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 0.2096(3) 0.4730(5) 0.2613(3) 0.0212 1.0000 Uani . . . . . .
N2 N 0.1686(3) 0.5688(6) 0.2119(3) 0.0293 1.0000 Uani . . . . . .
N3 N 0.2109(3) 0.5770(6) 0.1674(3) 0.0289 1.0000 Uani . . . . . .
C4 C 0.2799(4) 0.4876(6) 0.1892(3) 0.0208 1.0000 Uani . . . . . .
C5 C 0.2793(4) 0.4212(6) 0.2493(3) 0.0235 1.0000 Uani . . . . . .
C6 C 0.1800(4) 0.4404(6) 0.3184(3) 0.0202 1.0000 Uani . . . . . .
C7 C 0.1180(4) 0.3411(6) 0.3087(3) 0.0229 1.0000 Uani . . . . . .
C8 C 0.0899(4) 0.3055(6) 0.3637(3) 0.0236 1.0000 Uani . . . . . .
C9 C 0.1249(4) 0.3736(6) 0.4287(3) 0.0215 1.0000 Uani . . . . . .
C10 C 0.1876(4) 0.4740(6) 0.4412(3) 0.0230 1.0000 Uani . . . . . .
C11 C 0.2138(4) 0.5065(6) 0.3847(3) 0.0222 1.0000 Uani . . . . . .
Br12 Br 0.06544(4) 0.25752(7) 0.21587(3) 0.0325 1.0000 Uani . . . . . .
Br13 Br 0.08554(4) 0.33362(7) 0.50500(3) 0.0299 1.0000 Uani . . . . . .
Br14 Br 0.29652(5) 0.64545(7) 0.39875(4) 0.0342 1.0000 Uani . . . . . .
C15 C 0.3412(4) 0.4757(6) 0.1519(3) 0.0252 1.0000 Uani . . . . . .
C16 C 0.3133(4) 0.5034(7) 0.0775(4) 0.0307 1.0000 Uani . . . . . .
C17 C 0.3719(5) 0.4935(7) 0.0421(4) 0.0380 1.0000 Uani . . . . . .
C18 C 0.4606(5) 0.4603(8) 0.0825(5) 0.0440 1.0000 Uani . . . . . .
C19 C 0.4888(5) 0.4346(8) 0.1561(5) 0.0448 1.0000 Uani . . . . . .
C20 C 0.4304(4) 0.4419(7) 0.1912(4) 0.0346 1.0000 Uani . . . . . .
N101 N 0.2268(3) 0.2822(5) 0.7450(3) 0.0189 1.0000 Uani . . . . . .
N102 N 0.2181(3) 0.1587(5) 0.7153(3) 0.0249 1.0000 Uani . . . . . .
N103 N 0.2567(3) 0.1625(5) 0.6682(3) 0.0238 1.0000 Uani . . . . . .
C104 C 0.2907(3) 0.2859(5) 0.6682(3) 0.0173 1.0000 Uani . . . . . .
C105 C 0.2715(4) 0.3629(6) 0.7169(3) 0.0220 1.0000 Uani . . . . . .
C106 C 0.1877(4) 0.3116(6) 0.7967(3) 0.0201 1.0000 Uani . . . . . .
C107 C 0.2315(4) 0.2811(6) 0.8698(3) 0.0221 1.0000 Uani . . . . . .
C108 C 0.1928(4) 0.3035(6) 0.9201(3) 0.0249 1.0000 Uani . . . . . .
C109 C 0.1072(4) 0.3559(6) 0.8938(3) 0.0236 1.0000 Uani . . . . . .
C110 C 0.0618(4) 0.3885(6) 0.8218(3) 0.0279 1.0000 Uani . . . . . .
C111 C 0.1029(4) 0.3661(6) 0.7732(3) 0.0232 1.0000 Uani . . . . . .
Br112 Br 0.34797(4) 0.20876(8) 0.90452(4) 0.0395 1.0000 Uani . . . . . .
Br113 Br 0.05322(5) 0.38578(7) 0.96166(4) 0.0359 1.0000 Uani . . . . . .
Br114 Br 0.04255(5) 0.41216(8) 0.67375(4) 0.0419 1.0000 Uani . . . . . .
C115 C 0.3357(3) 0.3205(5) 0.6195(3) 0.0179 1.0000 Uani . . . . . .
C116 C 0.3769(4) 0.4434(6) 0.6244(3) 0.0256 1.0000 Uani . . . . . .
C117 C 0.4208(4) 0.4732(7) 0.5785(4) 0.0333 1.0000 Uani . . . . . .
C118 C 0.4225(4) 0.3833(7) 0.5268(4) 0.0359 1.0000 Uani . . . . . .
C119 C 0.3797(4) 0.2624(7) 0.5195(4) 0.0336 1.0000 Uani . . . . . .
C120 C 0.3371(4) 0.2303(6) 0.5664(3) 0.0246 1.0000 Uani . . . . . .
H101 H 0.2104 0.5175 0.4863 0.0262 1.0000 Uiso R . . . . .
H51 H 0.3181 0.3532 0.2758 0.0262 1.0000 Uiso R . . . . .
H201 H 0.4519 0.4251 0.2419 0.0401 1.0000 Uiso R . . . . .
H191 H 0.5487 0.4096 0.1829 0.0513 1.0000 Uiso R . . . . .
H181 H 0.5015 0.4554 0.0583 0.0509 1.0000 Uiso R . . . . .
H171 H 0.3515 0.5116 -0.0085 0.0431 1.0000 Uiso R . . . . .
H161 H 0.2533 0.5268 0.0503 0.0351 1.0000 Uiso R . . . . .
H81 H 0.0494 0.2356 0.3572 0.0267 1.0000 Uiso R . . . . .
H1081 H 0.2235 0.2849 0.9705 0.0281 1.0000 Uiso R . . . . .
H1101 H 0.0038 0.4253 0.8049 0.0318 1.0000 Uiso R . . . . .
H1051 H 0.2867 0.4527 0.7286 0.0242 1.0000 Uiso R . . . . .
H1161 H 0.3759 0.5055 0.6594 0.0294 1.0000 Uiso R . . . . .
H1171 H 0.4491 0.5573 0.5838 0.0404 1.0000 Uiso R . . . . .
H1181 H 0.4529 0.4037 0.4951 0.0423 1.0000 Uiso R . . . . .
H1191 H 0.3775 0.2006 0.4821 0.0371 1.0000 Uiso R . . . . .
H1201 H 0.3097 0.1468 0.5617 0.0272 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       130(6)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.070744(18)
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 . N2 . 1.353(7) yes
N1 . C5 . 1.352(7) yes
N1 . C6 . 1.429(7) yes
N2 . N3 . 1.315(7) yes
N3 . C4 . 1.373(7) yes
C4 . C5 . 1.368(8) yes
C4 . C15 . 1.460(8) yes
C5 . H51 . 0.943 no
C6 . C7 . 1.382(8) yes
C6 . C11 . 1.381(8) yes
C7 . C8 . 1.383(8) yes
C7 . Br12 . 1.896(6) yes
C8 . C9 . 1.372(8) yes
C8 . H81 . 0.939 no
C9 . C10 . 1.390(8) yes
C9 . Br13 . 1.899(5) yes
C10 . C11 . 1.383(8) yes
C10 . H101 . 0.932 no
C11 . Br14 . 1.889(6) yes
C15 . C16 . 1.390(9) yes
C15 . C20 . 1.398(9) yes
C16 . C17 . 1.391(9) yes
C16 . H161 . 0.944 no
C17 . C18 . 1.392(11) yes
C17 . H171 . 0.942 no
C18 . C19 . 1.370(11) yes
C18 . H181 . 0.960 no
C19 . C20 . 1.382(9) yes
C19 . H191 . 0.947 no
C20 . H201 . 0.939 no
N101 . N102 . 1.363(7) yes
N101 . C105 . 1.348(7) yes
N101 . C106 . 1.431(7) yes
N102 . N103 . 1.311(6) yes
N103 . C104 . 1.364(7) yes
C104 . C105 . 1.365(8) yes
C104 . C115 . 1.463(7) yes
C105 . H1051 . 0.944 no
C106 . C107 . 1.376(8) yes
C106 . C111 . 1.388(8) yes
C107 . C108 . 1.387(8) yes
C107 . Br112 . 1.895(5) yes
C108 . C109 . 1.390(8) yes
C108 . H1081 . 0.946 no
C109 . C110 . 1.366(9) yes
C109 . Br113 . 1.894(5) yes
C110 . C111 . 1.388(8) yes
C110 . H1101 . 0.946 no
C111 . Br114 . 1.884(6) yes
C115 . C116 . 1.395(8) yes
C115 . C120 . 1.398(8) yes
C116 . C117 . 1.390(8) yes
C116 . H1161 . 0.939 no
C117 . C118 . 1.377(10) yes
C117 . H1171 . 0.952 no
C118 . C119 . 1.385(10) yes
C118 . H1181 . 0.961 no
C119 . C120 . 1.396(8) yes
C119 . H1191 . 0.958 no
C120 . H1201 . 0.941 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
N2 . N1 . C5 . 111.2(5) yes
N2 . N1 . C6 . 120.9(5) yes
C5 . N1 . C6 . 127.9(5) yes
N1 . N2 . N3 . 106.8(5) yes
N2 . N3 . C4 . 109.1(5) yes
N3 . C4 . C5 . 108.2(5) yes
N3 . C4 . C15 . 122.2(5) yes
C5 . C4 . C15 . 129.6(5) yes
C4 . C5 . N1 . 104.7(5) yes
C4 . C5 . H51 . 127.6 no
N1 . C5 . H51 . 127.6 no
N1 . C6 . C7 . 120.6(5) yes
N1 . C6 . C11 . 120.5(5) yes
C7 . C6 . C11 . 118.8(5) yes
C6 . C7 . C8 . 121.8(5) yes
C6 . C7 . Br12 . 119.2(4) yes
C8 . C7 . Br12 . 118.9(4) yes
C7 . C8 . C9 . 117.6(5) yes
C7 . C8 . H81 . 121.2 no
C9 . C8 . H81 . 121.2 no
C8 . C9 . C10 . 122.8(5) yes
C8 . C9 . Br13 . 119.5(4) yes
C10 . C9 . Br13 . 117.7(4) yes
C9 . C10 . C11 . 117.7(5) yes
C9 . C10 . H101 . 120.4 no
C11 . C10 . H101 . 121.9 no
C10 . C11 . C6 . 121.3(5) yes
C10 . C11 . Br14 . 119.0(4) yes
C6 . C11 . Br14 . 119.7(4) yes
C4 . C15 . C16 . 120.9(6) yes
C4 . C15 . C20 . 120.4(6) yes
C16 . C15 . C20 . 118.7(6) yes
C15 . C16 . C17 . 120.9(6) yes
C15 . C16 . H161 . 119.6 no
C17 . C16 . H161 . 119.5 no
C16 . C17 . C18 . 119.4(6) yes
C16 . C17 . H171 . 119.6 no
C18 . C17 . H171 . 121.0 no
C17 . C18 . C19 . 120.0(6) yes
C17 . C18 . H181 . 119.5 no
C19 . C18 . H181 . 120.6 no
C18 . C19 . C20 . 120.9(7) yes
C18 . C19 . H191 . 119.6 no
C20 . C19 . H191 . 119.5 no
C15 . C20 . C19 . 120.2(7) yes
C15 . C20 . H201 . 120.9 no
C19 . C20 . H201 . 119.0 no
N102 . N101 . C105 . 110.9(5) yes
N102 . N101 . C106 . 119.9(4) yes
C105 . N101 . C106 . 129.2(5) yes
N101 . N102 . N103 . 106.3(4) yes
N102 . N103 . C104 . 109.5(5) yes
N103 . C104 . C105 . 108.4(5) yes
N103 . C104 . C115 . 121.7(5) yes
C105 . C104 . C115 . 129.8(5) yes
C104 . C105 . N101 . 104.8(5) yes
C104 . C105 . H1051 . 127.5 no
N101 . C105 . H1051 . 127.6 no
N101 . C106 . C107 . 120.9(5) yes
N101 . C106 . C111 . 120.2(5) yes
C107 . C106 . C111 . 118.8(5) yes
C106 . C107 . C108 . 121.6(5) yes
C106 . C107 . Br112 . 120.2(4) yes
C108 . C107 . Br112 . 118.2(4) yes
C107 . C108 . C109 . 117.6(5) yes
C107 . C108 . H1081 . 121.6 no
C109 . C108 . H1081 . 120.8 no
C108 . C109 . C110 . 122.6(5) yes
C108 . C109 . Br113 . 118.1(5) yes
C110 . C109 . Br113 . 119.3(4) yes
C109 . C110 . C111 . 118.2(5) yes
C109 . C110 . H1101 . 121.5 no
C111 . C110 . H1101 . 120.3 no
C110 . C111 . C106 . 121.2(5) yes
C110 . C111 . Br114 . 119.1(4) yes
C106 . C111 . Br114 . 119.7(4) yes
C104 . C115 . C116 . 121.1(5) yes
C104 . C115 . C120 . 119.9(5) yes
C116 . C115 . C120 . 118.9(5) yes
C115 . C116 . C117 . 120.2(6) yes
C115 . C116 . H1161 . 120.0 no
C117 . C116 . H1161 . 119.8 no
C116 . C117 . C118 . 120.5(6) yes
C116 . C117 . H1171 . 118.2 no
C118 . C117 . H1171 . 121.3 no
C117 . C118 . C119 . 120.2(6) yes
C117 . C118 . H1181 . 120.6 no
C119 . C118 . H1181 . 119.2 no
C118 . C119 . C120 . 119.7(6) yes
C118 . C119 . H1191 . 121.3 no
C120 . C119 . H1191 . 118.9 no
C115 . C120 . C119 . 120.4(6) yes
C115 . C120 . H1201 . 120.8 no
C119 . C120 . H1201 . 118.8 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
C105 . H1051 . N102 4_556 154.52(18) 0.944 2.372 3.250(9) yes




loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
1 0 1 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3aj
_database_code_depnum_ccdc_archive 'CCDC 1513615'
_audit_update_record             
;
2016-10-31 deposited with the CCDC.
2017-02-08 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          
; 
? 
;
_cell_length_a                   8.9462(5)
_cell_length_b                   11.9145(6)
_cell_length_c                   43.549(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4641.8(4)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  '-P 2ac 2ab '
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
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

_chemical_formula_sum            'C21 H34 N4 O2 Si1'
_chemical_formula_moiety         'C21 H34 N4 O2 Si1'
_chemical_compound_source        ?
_chemical_formula_weight         402.61


_cell_measurement_reflns_used    71
_cell_measurement_theta_min      8
_cell_measurement_theta_max      54
_cell_measurement_temperature    180

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.072
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_max          0.498

_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    1.065

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.93
_diffrn_measurement_device_type  'Bruker Kappa Apex3'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ scans'

_computing_data_collection       'Apex3 (Bruker AXS, 2015)'
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_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      180
_diffrn_ambient_pressure         101
_diffrn_reflns_number            34502
_reflns_number_total             4237
_diffrn_reflns_av_R_equivalents  0.058


_diffrn_reflns_theta_min         2.029
_diffrn_reflns_theta_max         68.283
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        68.283
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       48
_reflns_limit_h_min              0
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              52

_oxford_diffrn_Wilson_B_factor   2.66
_oxford_diffrn_Wilson_scale      12.01

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.32
_refine_diff_density_max         0.33


_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_oxford_refine_ls_R_factor_ref   0.0668
_refine_ls_wR_factor_ref         0.1162
_refine_ls_goodness_of_fit_ref   0.9617
_refine_ls_shift/su_max          0.0009209
_refine_ls_shift/su_mean         0.0000503

_oxford_reflns_number_all        4236
_refine_ls_R_factor_all          0.0668
_refine_ls_wR_factor_all         0.1162

_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3647
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_gt          0.1136

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_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: 
 18.7 27.3 13.0 3.21 
;


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 0.2527(2) 0.54394(15) 0.64496(4) 0.0311 1.0000 Uani . . . . . .
N2 N 0.3341(2) 0.62977(16) 0.63290(4) 0.0343 1.0000 Uani . . . . . .
N3 N 0.2571(2) 0.66956(15) 0.60992(4) 0.0336 1.0000 Uani . . . . . .
C4 C 0.1243(2) 0.61108(19) 0.60664(5) 0.0311 1.0000 Uani . . . . . .
C5 C 0.1219(2) 0.52954(18) 0.62929(5) 0.0308 1.0000 Uani . . . . . .
C6 C 0.3170(2) 0.47933(19) 0.66942(5) 0.0307 1.0000 Uani . . . . . .
C7 C 0.3247(3) 0.36401(19) 0.66680(5) 0.0370 1.0000 Uani . . . . . .
C8 C 0.3926(3) 0.3023(2) 0.68971(6) 0.0410 1.0000 Uani . . . . . .
C9 C 0.4529(3) 0.3581(2) 0.71440(5) 0.0387 1.0000 Uani . . . . . .
C10 C 0.4457(3) 0.4729(2) 0.71737(5) 0.0409 1.0000 Uani . . . . . .
C11 C 0.3758(3) 0.5345(2) 0.69469(5) 0.0377 1.0000 Uani . . . . . .
N12 N 0.5318(3) 0.2929(2) 0.73807(5) 0.0546 1.0000 Uani . . . . . .
O13 O 0.5207(3) 0.1909(2) 0.73727(5) 0.0816 1.0000 Uani . . . . . .
O14 O 0.6064(3) 0.3433(2) 0.75716(5) 0.0735 1.0000 Uani . . . . . .
Si15 Si 0.00065(7) 0.64547(5) 0.572694(13) 0.0327 1.0000 Uani . . . . . .
C16 C 0.0449(3) 0.7951(2) 0.56252(6) 0.0460 1.0000 Uani . . . . . .
C17 C -0.0186(4) 0.8332(3) 0.53154(7) 0.0670 1.0000 Uani . . . . . .
C18 C 0.0042(5) 0.8801(2) 0.58743(7) 0.0717 1.0000 Uani . . . . . .
C19 C 0.0611(3) 0.5502(2) 0.54052(6) 0.0446 1.0000 Uani . . . . . .
C20 C 0.2212(4) 0.5736(3) 0.53029(7) 0.0748 1.0000 Uani . . . . . .
C21 C 0.0398(4) 0.4264(2) 0.54863(7) 0.0642 1.0000 Uani . . . . . .
C22 C -0.2025(3) 0.6169(2) 0.58146(6) 0.0439 1.0000 Uani . . . . . .
C23 C -0.3036(3) 0.6372(3) 0.55357(7) 0.0602 1.0000 Uani . . . . . .
C24 C -0.2637(4) 0.6769(4) 0.60949(8) 0.0850 1.0000 Uani . . . . . .
C25 C 0.0035(3) 0.4475(2) 0.63874(5) 0.0370 1.0000 Uani . . . . . .
C26 C -0.0624(3) 0.4751(2) 0.67040(6) 0.0496 1.0000 Uani . . . . . .
C27 C -0.1932(3) 0.4006(3) 0.67940(7) 0.0609 1.0000 Uani . . . . . .
C28 C -0.1512(4) 0.2796(3) 0.68493(7) 0.0630 1.0000 Uani . . . . . .
H71 H 0.2836 0.3274 0.6494 0.0451 1.0000 Uiso R . . . . .
H81 H 0.3974 0.2228 0.6885 0.0495 1.0000 Uiso R . . . . .
H101 H 0.4880 0.5091 0.7347 0.0497 1.0000 Uiso R . . . . .
H111 H 0.3681 0.6138 0.6964 0.0459 1.0000 Uiso R . . . . .
H161 H 0.1505 0.7987 0.5605 0.0556 1.0000 Uiso R . . . . .
H171 H 0.0082 0.9093 0.5279 0.0814 1.0000 Uiso R . . . . .
H172 H -0.1245 0.8266 0.5318 0.0814 1.0000 Uiso R . . . . .
H173 H 0.0209 0.7874 0.5156 0.0814 1.0000 Uiso R . . . . .
H181 H 0.0297 0.9536 0.5808 0.0876 1.0000 Uiso R . . . . .
H182 H 0.0575 0.8630 0.6057 0.0876 1.0000 Uiso R . . . . .
H183 H -0.1001 0.8763 0.5913 0.0876 1.0000 Uiso R . . . . .
H191 H -0.0018 0.5658 0.5235 0.0539 1.0000 Uiso R . . . . .
H201 H 0.2474 0.5241 0.5141 0.0901 1.0000 Uiso R . . . . .
H202 H 0.2871 0.5623 0.5471 0.0901 1.0000 Uiso R . . . . .
H203 H 0.2290 0.6490 0.5234 0.0901 1.0000 Uiso R . . . . .
H211 H 0.0713 0.3811 0.5319 0.0777 1.0000 Uiso R . . . . .
H212 H 0.0976 0.4087 0.5663 0.0777 1.0000 Uiso R . . . . .
H213 H -0.0628 0.4125 0.5528 0.0777 1.0000 Uiso R . . . . .
H221 H -0.2091 0.5390 0.5859 0.0534 1.0000 Uiso R . . . . .
H231 H -0.4045 0.6219 0.5589 0.0731 1.0000 Uiso R . . . . .
H232 H -0.2948 0.7131 0.5472 0.0731 1.0000 Uiso R . . . . .
H233 H -0.2739 0.5890 0.5373 0.0731 1.0000 Uiso R . . . . .
H241 H -0.3660 0.6580 0.6122 0.1030 1.0000 Uiso R . . . . .
H242 H -0.2085 0.6547 0.6271 0.1030 1.0000 Uiso R . . . . .
H243 H -0.2546 0.7557 0.6067 0.1030 1.0000 Uiso R . . . . .
H251 H 0.0462 0.3745 0.6394 0.0450 1.0000 Uiso R . . . . .
H252 H -0.0747 0.4488 0.6240 0.0450 1.0000 Uiso R . . . . .
H261 H 0.0141 0.4664 0.6853 0.0600 1.0000 Uiso R . . . . .
H262 H -0.0953 0.5509 0.6702 0.0600 1.0000 Uiso R . . . . .
H271 H -0.2362 0.4296 0.6977 0.0736 1.0000 Uiso R . . . . .
H272 H -0.2649 0.4030 0.6633 0.0736 1.0000 Uiso R . . . . .
H281 H -0.2378 0.2381 0.6904 0.0762 1.0000 Uiso R . . . . .
H282 H -0.0802 0.2756 0.7011 0.0762 1.0000 Uiso R . . . . .
H283 H -0.1090 0.2491 0.6668 0.0762 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3162(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 . N2 . 1.361(3) yes
N1 . C5 . 1.365(3) yes
N1 . C6 . 1.434(3) yes
N2 . N3 . 1.305(3) yes
N3 . C4 . 1.384(3) yes
C4 . C5 . 1.385(3) yes
C4 . Si15 . 1.891(2) yes
C5 . C25 . 1.499(3) yes
C6 . C7 . 1.380(3) yes
C6 . C11 . 1.385(3) yes
C7 . C8 . 1.380(3) yes
C7 . H71 . 0.950 no
C8 . C9 . 1.374(3) yes
C8 . H81 . 0.950 no
C9 . C10 . 1.375(4) yes
C9 . N12 . 1.472(3) yes
C10 . C11 . 1.380(3) yes
C10 . H101 . 0.950 no
C11 . H111 . 0.950 no
N12 . O13 . 1.219(3) yes
N12 . O14 . 1.224(3) yes
Si15 . C16 . 1.879(3) yes
Si15 . C19 . 1.882(2) yes
Si15 . C22 . 1.888(3) yes
C16 . C17 . 1.533(3) yes
C16 . C18 . 1.528(4) yes
C16 . H161 . 0.950 no
C17 . H171 . 0.950 no
C17 . H172 . 0.950 no
C17 . H173 . 0.950 no
C18 . H181 . 0.950 no
C18 . H182 . 0.950 no
C18 . H183 . 0.950 no
C19 . C20 . 1.526(4) yes
C19 . C21 . 1.529(4) yes
C19 . H191 . 0.950 no
C20 . H201 . 0.950 no
C20 . H202 . 0.950 no
C20 . H203 . 0.950 no
C21 . H211 . 0.950 no
C21 . H212 . 0.950 no
C21 . H213 . 0.950 no
C22 . C23 . 1.533(4) yes
C22 . C24 . 1.517(4) yes
C22 . H221 . 0.950 no
C23 . H231 . 0.950 no
C23 . H232 . 0.950 no
C23 . H233 . 0.950 no
C24 . H241 . 0.950 no
C24 . H242 . 0.950 no
C24 . H243 . 0.950 no
C25 . C26 . 1.535(3) yes
C25 . H251 . 0.950 no
C25 . H252 . 0.950 no
C26 . C27 . 1.520(4) yes
C26 . H261 . 0.950 no
C26 . H262 . 0.950 no
C27 . C28 . 1.509(4) yes
C27 . H271 . 0.950 no
C27 . H272 . 0.950 no
C28 . H281 . 0.950 no
C28 . H282 . 0.950 no
C28 . H283 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 . N1 . C5 . 111.10(17) yes
N2 . N1 . C6 . 118.38(18) yes
C5 . N1 . C6 . 130.34(19) yes
N1 . N2 . N3 . 106.64(17) yes
N2 . N3 . C4 . 110.47(18) yes
N3 . C4 . C5 . 107.03(19) yes
N3 . C4 . Si15 . 118.25(16) yes
C5 . C4 . Si15 . 134.41(17) yes
C4 . C5 . N1 . 104.76(19) yes
C4 . C5 . C25 . 131.6(2) yes
N1 . C5 . C25 . 123.38(19) yes
N1 . C6 . C7 . 119.5(2) yes
N1 . C6 . C11 . 119.2(2) yes
C7 . C6 . C11 . 121.2(2) yes
C6 . C7 . C8 . 119.5(2) yes
C6 . C7 . H71 . 120.2 no
C8 . C7 . H71 . 120.3 no
C7 . C8 . C9 . 118.7(2) yes
C7 . C8 . H81 . 120.7 no
C9 . C8 . H81 . 120.6 no
C8 . C9 . C10 . 122.4(2) yes
C8 . C9 . N12 . 118.7(2) yes
C10 . C9 . N12 . 118.8(2) yes
C9 . C10 . C11 . 118.9(2) yes
C9 . C10 . H101 . 120.6 no
C11 . C10 . H101 . 120.6 no
C6 . C11 . C10 . 119.2(2) yes
C6 . C11 . H111 . 120.4 no
C10 . C11 . H111 . 120.4 no
C9 . N12 . O13 . 117.8(3) yes
C9 . N12 . O14 . 118.6(2) yes
O13 . N12 . O14 . 123.6(3) yes
C4 . Si15 . C16 . 105.47(11) yes
C4 . Si15 . C19 . 106.45(11) yes
C16 . Si15 . C19 . 109.63(12) yes
C4 . Si15 . C22 . 111.47(10) yes
C16 . Si15 . C22 . 114.91(13) yes
C19 . Si15 . C22 . 108.57(12) yes
Si15 . C16 . C17 . 114.27(18) yes
Si15 . C16 . C18 . 114.3(2) yes
C17 . C16 . C18 . 109.9(2) yes
Si15 . C16 . H161 . 105.9 no
C17 . C16 . H161 . 106.0 no
C18 . C16 . H161 . 105.7 no
C16 . C17 . H171 . 109.5 no
C16 . C17 . H172 . 109.4 no
H171 . C17 . H172 . 109.5 no
C16 . C17 . H173 . 109.4 no
H171 . C17 . H173 . 109.5 no
H172 . C17 . H173 . 109.5 no
C16 . C18 . H181 . 109.7 no
C16 . C18 . H182 . 109.5 no
H181 . C18 . H182 . 109.5 no
C16 . C18 . H183 . 109.2 no
H181 . C18 . H183 . 109.5 no
H182 . C18 . H183 . 109.5 no
Si15 . C19 . C20 . 112.2(2) yes
Si15 . C19 . C21 . 111.96(19) yes
C20 . C19 . C21 . 111.1(3) yes
Si15 . C19 . H191 . 107.1 no
C20 . C19 . H191 . 107.0 no
C21 . C19 . H191 . 107.1 no
C19 . C20 . H201 . 109.6 no
C19 . C20 . H202 . 109.3 no
H201 . C20 . H202 . 109.5 no
C19 . C20 . H203 . 109.5 no
H201 . C20 . H203 . 109.5 no
H202 . C20 . H203 . 109.5 no
C19 . C21 . H211 . 109.5 no
C19 . C21 . H212 . 109.4 no
H211 . C21 . H212 . 109.5 no
C19 . C21 . H213 . 109.4 no
H211 . C21 . H213 . 109.5 no
H212 . C21 . H213 . 109.5 no
Si15 . C22 . C23 . 112.29(18) yes
Si15 . C22 . C24 . 115.2(2) yes
C23 . C22 . C24 . 110.5(2) yes
Si15 . C22 . H221 . 106.1 no
C23 . C22 . H221 . 106.1 no
C24 . C22 . H221 . 106.0 no
C22 . C23 . H231 . 109.6 no
C22 . C23 . H232 . 109.5 no
H231 . C23 . H232 . 109.5 no
C22 . C23 . H233 . 109.3 no
H231 . C23 . H233 . 109.5 no
H232 . C23 . H233 . 109.5 no
C22 . C24 . H241 . 109.7 no
C22 . C24 . H242 . 109.3 no
H241 . C24 . H242 . 109.5 no
C22 . C24 . H243 . 109.4 no
H241 . C24 . H243 . 109.5 no
H242 . C24 . H243 . 109.5 no
C5 . C25 . C26 . 112.20(19) yes
C5 . C25 . H251 . 108.7 no
C26 . C25 . H251 . 108.8 no
C5 . C25 . H252 . 108.9 no
C26 . C25 . H252 . 108.7 no
H251 . C25 . H252 . 109.5 no
C25 . C26 . C27 . 113.7(2) yes
C25 . C26 . H261 . 108.4 no
C27 . C26 . H261 . 108.3 no
C25 . C26 . H262 . 108.4 no
C27 . C26 . H262 . 108.6 no
H261 . C26 . H262 . 109.5 no
C26 . C27 . C28 . 114.0(3) yes
C26 . C27 . H271 . 108.4 no
C28 . C27 . H271 . 108.3 no
C26 . C27 . H272 . 108.2 no
C28 . C27 . H272 . 108.3 no
H271 . C27 . H272 . 109.5 no
C27 . C28 . H281 . 109.6 no
C27 . C28 . H282 . 109.4 no
H281 . C28 . H282 . 109.5 no
C27 . C28 . H283 . 109.4 no
H281 . C28 . H283 . 109.5 no
H282 . C28 . H283 . 109.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 . H71 . N3 8_545 158 0.950 2.573 3.470(4) yes
C10 . H101 . O13 4_656 141 0.950 2.487 3.278(4) yes
C28 . H282 . O14 6_456 159 0.950 2.596 3.499(4) yes


_iucr_refine_instruction_details_constraints 
;
BLOCK SCALE X'S, U'S 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) H   ( 173,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) H   ( 243,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) H   ( 283,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
