# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CRYSTALS_cif
#TrackingRef '5052_web_deposit_cif_file_0_YuliaBorozdina_1302869620.cif'

_audit_creation_date             07-09-18
_audit_creation_method           CRYSTALS_ver_12.39

_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   13.0450(5)
_cell_length_b                   8.4470(4)
_cell_length_c                   13.7030(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.5930(12)
_cell_angle_gamma                90
_cell_volume                     1509.37(11)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 n 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y,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'
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'
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'


_cell_formula_units_Z            4

# Given Formula = C17 H20 N2 O3
# Dc = 1.32 Fooo = 640.00 Mu = 0.91 M = 600.71
# Found Formula = C17 H20 N2 O3
# Dc = 1.32 FOOO = 640.00 Mu = 0.91 M = 600.71

_chemical_formula_sum            'C17 H20 N2 O3'
_chemical_formula_moiety         'C17 H20 N2 O3'
_chemical_compound_source        ?
_chemical_formula_weight         300.36


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    293

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_max          ?

_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.091

# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_T_max  1.0000
_diffrn_measurement_device_type  Unknown
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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      293
_diffrn_reflns_number            19793
_reflns_number_total             4156
_diffrn_reflns_av_R_equivalents  0.054
# Number of reflections with Friedels Law is 4156
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 4203


_diffrn_reflns_theta_min         4.106
_diffrn_reflns_theta_max         29.498
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        25.073
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -18
_reflns_limit_h_max              18
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              18


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

_refine_diff_density_min         -0.65
_refine_diff_density_max         0.78


_refine_ls_number_reflns         1427
_refine_ls_number_restraints     2
_refine_ls_number_parameters     193

#_refine_ls_R_factor_ref 0.0941
_refine_ls_wR_factor_ref         0.0942
_refine_ls_goodness_of_fit_ref   5.6334

#_reflns_number_all 4156
_refine_ls_R_factor_all          0.2194
_refine_ls_wR_factor_all         0.2797

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                1427
_refine_ls_R_factor_gt           0.0941
_refine_ls_wR_factor_gt          0.0942

_refine_ls_shift/su_max          1.293694

# 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 unk


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed

# WARNING. The IUCr will not accept Unit Weights
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Quasi-Unit weights
W = 1.0 or 1./2F
;

# 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
C1 C 0.5434(16) 0.602(3) 0.8412(15) 0.027(5) 1.0000 Uiso . . . . . .
C2 C 0.6520(15) 0.636(3) 0.8689(14) 0.027(5) 1.0000 Uiso . . . . . .
C3 C 0.7235(18) 0.536(3) 0.8341(16) 0.032(6) 1.0000 Uiso . . . . . .
C4 C 0.7005(17) 0.396(3) 0.7825(15) 0.025(5) 1.0000 Uiso . . . . . .
C5 C 0.6055(15) 0.373(2) 0.7544(13) 0.025(4) 1.0000 Uiso . . . . . .
C6 C 0.5244(14) 0.475(2) 0.7766(13) 0.020(4) 1.0000 Uiso . . . . . .
C7 C 0.847(3) 0.692(4) 0.923(2) 0.087(11) 1.0000 Uiso . . . . . .
C8 C 0.3972(15) 0.305(2) 0.6984(14) 0.032(5) 1.0000 Uiso . . . . . .
C11 C 0.4622(19) 0.713(3) 0.8757(18) 0.036(6) 1.0000 Uiso . . . . . .
C12 C 0.476(2) 0.873(3) 0.8712(18) 0.038(6) 1.0000 Uiso . . . . . .
C13 C 0.4027(15) 0.977(2) 0.9049(15) 0.023(4) 1.0000 Uiso . . . . . .
C14 C 0.3150(18) 0.920(3) 0.9406(18) 0.032(6) 1.0000 Uiso . . . . . .
C15 C 0.2984(13) 0.758(2) 0.9490(12) 0.018(4) 1.0000 Uiso . . . . . .
C16 C 0.3691(15) 0.656(3) 0.9073(15) 0.024(5) 1.0000 Uiso . . . . . .
C17 C 0.2349(18) 1.026(3) 0.9691(17) 0.032(6) 1.0000 Uiso . . . . . .
C18 C 0.1437(14) 1.276(2) 0.9901(13) 0.021(4) 1.0000 Uiso . . . . . .
C19 C 0.0735(15) 1.131(2) 1.0141(14) 0.025(4) 1.0000 Uiso . . . . . .
C20 C 0.1964(14) 1.352(3) 1.0765(14) 0.049(5) 1.0000 Uiso . . . . . .
C21 C 0.0914(13) 1.388(2) 0.9248(13) 0.045(4) 1.0000 Uiso . . . . . .
C22 C 0.034(2) 1.134(4) 1.1153(18) 0.063(8) 1.0000 Uiso . . . . . .
C23 C -0.0052(18) 1.087(3) 0.9437(17) 0.068(7) 1.0000 Uiso . . . . . .
C31 C 0.7836(16) 0.293(2) 0.7483(15) 0.023(5) 1.0000 Uiso . . . . . .
C32 C 0.8711(17) 0.348(3) 0.7069(16) 0.036(5) 1.0000 Uiso . . . . . .
C33 C 0.9493(18) 0.247(3) 0.6831(15) 0.039(5) 1.0000 Uiso . . . . . .
C34 C 0.9351(17) 0.082(3) 0.6802(16) 0.026(5) 1.0000 Uiso . . . . . .
C35 C 0.8375(17) 0.026(3) 0.7145(17) 0.035(6) 1.0000 Uiso . . . . . .
C36 C 0.7665(16) 0.127(3) 0.7452(15) 0.025(5) 1.0000 Uiso . . . . . .
C37 C 1.0152(16) -0.029(3) 0.6546(16) 0.029(5) 1.0000 Uiso . . . . . .
C38 C 1.170(2) -0.132(4) 0.603(2) 0.060(8) 1.0000 Uiso . . . . . .
C39 C 1.1017(19) -0.258(3) 0.6245(18) 0.043(6) 1.0000 Uiso . . . . . .
C40 C 1.2694(18) -0.128(3) 0.6677(17) 0.065(7) 1.0000 Uiso . . . . . .
C41 C 1.197(2) -0.123(4) 0.4969(19) 0.070(9) 1.0000 Uiso . . . . . .
C42 C 1.1198(17) -0.342(3) 0.7288(15) 0.073(7) 1.0000 Uiso . . . . . .
C43 C 1.083(2) -0.387(3) 0.5528(19) 0.088(9) 1.0000 Uiso . . . . . .
O1 O 0.8260(13) 0.555(2) 0.8621(12) 0.052(5) 1.0000 Uiso . . . . . .
O2 O 0.4250(11) 0.4560(16) 0.7423(11) 0.036(3) 1.0000 Uiso . . . . . .
O11 O 0.311(4) 1.266(6) 0.936(4) 0.33(3) 1.0000 Uiso . . . . . .
O12 O 0.1279(17) 0.857(3) 1.0506(16) 0.104(7) 1.0000 Uiso . . . . . .
N11 N 0.229(2) 1.180(4) 0.951(2) 0.105(10) 1.0000 Uiso . . . . . .
N12 N 0.1516(17) 0.993(3) 1.0085(15) 0.063(6) 1.0000 Uiso . . . . . .
O31 O 1.1603(16) 0.134(3) 0.6640(16) 0.061(6) 0.6201 Uiso . . . . . .
O32 O 0.9599(10) -0.2599(15) 0.7362(9) 0.013(3) 0.6201 Uiso . . . . . .
N31 N 1.1187(17) 0.002(3) 0.6470(17) 0.034(5) 0.6201 Uiso . . . . . .
N32 N 1.0153(14) -0.186(2) 0.6802(14) 0.012(4) 0.6201 Uiso . . . . . .
O311 O 1.1207(15) 0.138(3) 0.5667(15) 0.001(4) 0.3799 Uiso . . . . . .
O321 O 0.9184(16) -0.257(3) 0.6140(16) 0.015(4) 0.3799 Uiso . . . . . .
N311 N 1.0942(19) 0.008(3) 0.5947(19) -0.002(5) 0.3799 Uiso . . . . . .
N321 N 1.0017(16) -0.181(2) 0.6222(16) -0.005(4) 0.3799 Uiso . . . . . .
H21 H 0.6705 0.7226 0.9100 0.0441 1.0000 Uiso R . . . . .
H51 H 0.5899 0.2840 0.7145 0.0252 1.0000 Uiso R . . . . .
H71 H 0.9183 0.7004 0.9394 0.1113 1.0000 Uiso R . . . . .
H72 H 0.8102 0.6748 0.9811 0.1113 1.0000 Uiso R . . . . .
H73 H 0.8243 0.7880 0.8934 0.1113 1.0000 Uiso R . . . . .
H81 H 0.3275 0.3085 0.6764 0.0303 1.0000 Uiso R . . . . .
H82 H 0.4054 0.2261 0.7474 0.0303 1.0000 Uiso R . . . . .
H83 H 0.4394 0.2805 0.6451 0.0303 1.0000 Uiso R . . . . .
H121 H 0.5401 0.9133 0.8501 0.0461 1.0000 Uiso R . . . . .
H131 H 0.4135 1.0881 0.8998 0.0220 1.0000 Uiso R . . . . .
H151 H 0.2391 0.7196 0.9798 0.0177 1.0000 Uiso R . . . . .
H161 H 0.3541 0.5461 0.9032 0.0446 1.0000 Uiso R . . . . .
H201 H 0.2376 1.4381 1.0571 0.0675 1.0000 Uiso R . . . . .
H202 H 0.1455 1.3882 1.1194 0.0675 1.0000 Uiso R . . . . .
H203 H 0.2382 1.2749 1.1091 0.0675 1.0000 Uiso R . . . . .
H211 H 0.1358 1.4731 0.9104 0.0607 1.0000 Uiso R . . . . .
H212 H 0.0332 1.4266 0.9572 0.0607 1.0000 Uiso R . . . . .
H213 H 0.0699 1.3369 0.8658 0.0607 1.0000 Uiso R . . . . .
H221 H -0.0068 1.0423 1.1239 0.0924 1.0000 Uiso R . . . . .
H222 H 0.0902 1.1324 1.1612 0.0924 1.0000 Uiso R . . . . .
H223 H -0.0059 1.2259 1.1251 0.0924 1.0000 Uiso R . . . . .
H231 H -0.0418 0.9989 0.9679 0.0639 1.0000 Uiso R . . . . .
H232 H -0.0509 1.1737 0.9340 0.0639 1.0000 Uiso R . . . . .
H233 H 0.0245 1.0600 0.8835 0.0639 1.0000 Uiso R . . . . .
H321 H 0.8789 0.4590 0.6983 0.0335 1.0000 Uiso R . . . . .
H331 H 1.0145 0.2891 0.6679 0.0518 1.0000 Uiso R . . . . .
H351 H 0.8237 -0.0844 0.7139 0.0569 1.0000 Uiso R . . . . .
H361 H 0.7041 0.0878 0.7701 0.0390 1.0000 Uiso R . . . . .
H401 H 1.3150 -0.0447 0.6515 0.0721 1.0000 Uiso R . . . . .
H402 H 1.3033 -0.2266 0.6618 0.0721 1.0000 Uiso R . . . . .
H403 H 1.2482 -0.1143 0.7329 0.0721 1.0000 Uiso R . . . . .
H411 H 1.2446 -0.0398 0.4843 0.0785 1.0000 Uiso R . . . . .
H412 H 1.2262 -0.2211 0.4782 0.0785 1.0000 Uiso R . . . . .
H413 H 1.1355 -0.1048 0.4606 0.0785 1.0000 Uiso R . . . . .
H421 H 1.1370 -0.2612 0.7747 0.0893 1.0000 Uiso R . . . . .
H422 H 1.1740 -0.4169 0.7270 0.0893 1.0000 Uiso R . . . . .
H423 H 1.0586 -0.3932 0.7475 0.0893 1.0000 Uiso R . . . . .
H431 H 1.0730 -0.3398 0.4904 0.1088 1.0000 Uiso R . . . . .
H432 H 1.1369 -0.4625 0.5504 0.1088 1.0000 Uiso R . . . . .
H433 H 1.0216 -0.4388 0.5709 0.1088 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None

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
C1 . C2 . 1.48(3) yes
C1 . C6 . 1.41(3) yes
C1 . C11 . 1.50(3) yes
C2 . C3 . 1.35(3) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.41(3) yes
C3 . O1 . 1.39(3) yes
C4 . C5 . 1.30(3) yes
C4 . C31 . 1.48(3) yes
C5 . C6 . 1.40(3) yes
C5 . H51 . 0.950 no
C6 . O2 . 1.38(2) yes
C7 . O1 . 1.45(3) yes
C7 . H71 . 0.950 no
C7 . H72 . 0.950 no
C7 . H73 . 0.950 no
C8 . O2 . 1.45(2) yes
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C8 . H83 . 0.950 no
C11 . C12 . 1.36(3) yes
C11 . C16 . 1.39(3) yes
C12 . C13 . 1.39(3) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.35(3) yes
C13 . H131 . 0.950 no
C14 . C15 . 1.39(3) yes
C14 . C17 . 1.44(3) yes
C15 . C16 . 1.40(2) yes
C15 . H151 . 0.950 no
C16 . H161 . 0.950 no
C17 . N11 . 1.32(4) yes
C17 . N12 . 1.26(3) yes
C18 . C19 . 1.56(3) yes
C18 . C20 . 1.50(3) yes
C18 . C21 . 1.46(2) yes
C18 . N11 . 1.49(3) yes
C19 . C22 . 1.49(3) yes
C19 . C23 . 1.44(3) yes
C19 . N12 . 1.56(3) yes
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 . H221 . 0.950 no
C22 . H222 . 0.950 no
C22 . H223 . 0.950 no
C23 . H231 . 0.950 no
C23 . H232 . 0.950 no
C23 . H233 . 0.950 no
C31 . C32 . 1.37(3) yes
C31 . C36 . 1.42(3) yes
C32 . C33 . 1.38(3) yes
C32 . H321 . 0.950 no
C33 . C34 . 1.41(3) yes
C33 . H331 . 0.950 no
C34 . C35 . 1.45(3) yes
C34 . C37 . 1.46(3) yes
C35 . C36 . 1.33(3) yes
C35 . H351 . 0.950 no
C36 . H361 . 0.950 no
C37 . N31 . 1.38(3) yes
C37 . N32 . 1.37(3) yes
C37 . N311 . 1.37(3) yes
C37 . N321 . 1.37(3) yes
C38 . C39 . 1.43(4) yes
C38 . C40 . 1.55(3) yes
C38 . C41 . 1.51(4) yes
C38 . N31 . 1.45(4) yes
C38 . N311 . 1.54(4) yes
C39 . C42 . 1.61(3) yes
C39 . C43 . 1.48(3) yes
C39 . N32 . 1.51(3) yes
C39 . N321 . 1.46(3) yes
C40 . H401 . 0.950 no
C40 . H402 . 0.950 no
C40 . H403 . 0.950 no
C41 . H411 . 0.950 no
C41 . H412 . 0.950 no
C41 . H413 . 0.950 no
C42 . H421 . 0.950 no
C42 . H422 . 0.950 no
C42 . H423 . 0.950 no
C43 . H431 . 0.950 no
C43 . H432 . 0.950 no
C43 . H433 . 0.950 no
O11 . N11 . 1.32(5) yes
O12 . N12 . 1.33(3) yes
O31 . N31 . 1.26(3) yes
O31 . O311 . 1.42(3) yes
O31 . N311 . 1.65(3) yes
O32 . N32 . 1.24(2) yes
O32 . O321 . 1.75(3) yes
O32 . N321 . 1.80(3) yes
N31 . O311 . 1.59(3) yes
N31 . N311 . 0.78(3) yes
N32 . O321 . 1.65(3) yes
N32 . N321 . 0.81(3) yes
O311 . N311 . 1.22(3) yes
O321 . N321 . 1.26(3) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C6 . 117.1(19) yes
C2 . C1 . C11 . 118.5(18) yes
C6 . C1 . C11 . 124.2(20) yes
C1 . C2 . C3 . 117(2) yes
C1 . C2 . H21 . 121.582 no
C3 . C2 . H21 . 121.476 no
C2 . C3 . C4 . 124(2) yes
C2 . C3 . O1 . 120(2) yes
C4 . C3 . O1 . 115(2) yes
C3 . C4 . C5 . 118(2) yes
C3 . C4 . C31 . 121(2) yes
C5 . C4 . C31 . 121.1(20) yes
C4 . C5 . C6 . 124(2) yes
C4 . C5 . H51 . 118.437 no
C6 . C5 . H51 . 117.308 no
C1 . C6 . C5 . 118.8(20) yes
C1 . C6 . O2 . 116.6(17) yes
C5 . C6 . O2 . 124.5(18) yes
O1 . C7 . H71 . 110.982 no
O1 . C7 . H72 . 105.269 no
H71 . C7 . H72 . 109.476 no
O1 . C7 . H73 . 112.061 no
H71 . C7 . H73 . 109.475 no
H72 . C7 . H73 . 109.477 no
O2 . C8 . H81 . 109.245 no
O2 . C8 . H82 . 107.619 no
H81 . C8 . H82 . 109.476 no
O2 . C8 . H83 . 111.512 no
H81 . C8 . H83 . 109.475 no
H82 . C8 . H83 . 109.477 no
C1 . C11 . C12 . 120(2) yes
C1 . C11 . C16 . 121(2) yes
C12 . C11 . C16 . 119(2) yes
C11 . C12 . C13 . 121(2) yes
C11 . C12 . H121 . 119.389 no
C13 . C12 . H121 . 119.360 no
C12 . C13 . C14 . 120(2) yes
C12 . C13 . H131 . 119.616 no
C14 . C13 . H131 . 120.576 no
C13 . C14 . C15 . 121(2) yes
C13 . C14 . C17 . 120(2) yes
C15 . C14 . C17 . 118(2) yes
C14 . C15 . C16 . 118.0(18) yes
C14 . C15 . H151 . 120.436 no
C16 . C15 . H151 . 121.543 no
C15 . C16 . C11 . 120.2(20) yes
C15 . C16 . H161 . 119.419 no
C11 . C16 . H161 . 120.287 no
C14 . C17 . N11 . 127(2) yes
C14 . C17 . N12 . 128(2) yes
N11 . C17 . N12 . 105(3) yes
C19 . C18 . C20 . 115.2(16) yes
C19 . C18 . C21 . 111.5(16) yes
C20 . C18 . C21 . 113.8(16) yes
C19 . C18 . N11 . 95.9(17) yes
C20 . C18 . N11 . 100.7(17) yes
C21 . C18 . N11 . 118.3(18) yes
C18 . C19 . C22 . 113.7(19) yes
C18 . C19 . C23 . 118.2(18) yes
C22 . C19 . C23 . 112(2) yes
C18 . C19 . N12 . 100.7(15) yes
C22 . C19 . N12 . 107.4(19) yes
C23 . C19 . N12 . 103.2(18) yes
C18 . C20 . H201 . 111.064 no
C18 . C20 . H202 . 108.448 no
H201 . C20 . H202 . 109.475 no
C18 . C20 . H203 . 108.876 no
H201 . C20 . H203 . 109.476 no
H202 . C20 . H203 . 109.476 no
C18 . C21 . H211 . 110.079 no
C18 . C21 . H212 . 107.690 no
H211 . C21 . H212 . 109.475 no
C18 . C21 . H213 . 110.615 no
H211 . C21 . H213 . 109.476 no
H212 . C21 . H213 . 109.477 no
C19 . C22 . H221 . 108.264 no
C19 . C22 . H222 . 109.792 no
H221 . C22 . H222 . 109.476 no
C19 . C22 . H223 . 110.338 no
H221 . C22 . H223 . 109.475 no
H222 . C22 . H223 . 109.475 no
C19 . C23 . H231 . 109.075 no
C19 . C23 . H232 . 109.118 no
H231 . C23 . H232 . 109.475 no
C19 . C23 . H233 . 110.204 no
H231 . C23 . H233 . 109.476 no
H232 . C23 . H233 . 109.476 no
C4 . C31 . C32 . 123.6(20) yes
C4 . C31 . C36 . 118.6(19) yes
C32 . C31 . C36 . 117(2) yes
C31 . C32 . C33 . 121(2) yes
C31 . C32 . H321 . 118.839 no
C33 . C32 . H321 . 119.920 no
C32 . C33 . C34 . 122(2) yes
C32 . C33 . H331 . 119.623 no
C34 . C33 . H331 . 118.837 no
C33 . C34 . C35 . 116(2) yes
C33 . C34 . C37 . 124(2) yes
C35 . C34 . C37 . 120.6(19) yes
C34 . C35 . C36 . 121(2) yes
C34 . C35 . H351 . 119.081 no
C36 . C35 . H351 . 119.712 no
C31 . C36 . C35 . 122(2) yes
C31 . C36 . H361 . 117.745 no
C35 . C36 . H361 . 120.179 no
C34 . C37 . N31 . 127(2) yes
C34 . C37 . N32 . 124.0(20) yes
N31 . C37 . N32 . 102.0(19) yes
C34 . C37 . N311 . 123(2) yes
N31 . C37 . N311 . 32.8(14) yes
N32 . C37 . N311 . 112(2) yes
C34 . C37 . N321 . 126.8(20) yes
N31 . C37 . N321 . 105.6(19) yes
N32 . C37 . N321 . 34.4(13) yes
N311 . C37 . N321 . 96.5(19) yes
C39 . C38 . C40 . 114(2) yes
C39 . C38 . C41 . 114(3) yes
C40 . C38 . C41 . 110(2) yes
C39 . C38 . N31 . 101(2) yes
C40 . C38 . N31 . 98(2) yes
C41 . C38 . N31 . 119(3) yes
C39 . C38 . N311 . 100(2) yes
C40 . C38 . N311 . 123(3) yes
C41 . C38 . N311 . 93(2) yes
N31 . C38 . N311 . 29.9(14) yes
C38 . C39 . C42 . 116(2) yes
C38 . C39 . C43 . 120(2) yes
C42 . C39 . C43 . 106.5(19) yes
C38 . C39 . N32 . 106(2) yes
C42 . C39 . N32 . 79.6(16) yes
C43 . C39 . N32 . 121(2) yes
C38 . C39 . N321 . 103(2) yes
C42 . C39 . N321 . 109.0(20) yes
C43 . C39 . N321 . 101(2) yes
N32 . C39 . N321 . 31.7(12) yes
C38 . C40 . H401 . 113.528 no
C38 . C40 . H402 . 108.450 no
H401 . C40 . H402 . 109.476 no
C38 . C40 . H403 . 106.342 no
H401 . C40 . H403 . 109.475 no
H402 . C40 . H403 . 109.476 no
C38 . C41 . H411 . 112.475 no
C38 . C41 . H412 . 108.824 no
H411 . C41 . H412 . 109.475 no
C38 . C41 . H413 . 107.056 no
H411 . C41 . H413 . 109.475 no
H412 . C41 . H413 . 109.476 no
C39 . C42 . H421 . 107.457 no
C39 . C42 . H422 . 111.222 no
H421 . C42 . H422 . 109.475 no
C39 . C42 . H423 . 109.699 no
H421 . C42 . H423 . 109.475 no
H422 . C42 . H423 . 109.476 no
C39 . C43 . H431 . 107.601 no
C39 . C43 . H432 . 113.948 no
H431 . C43 . H432 . 109.476 no
C39 . C43 . H433 . 106.760 no
H431 . C43 . H433 . 109.476 no
H432 . C43 . H433 . 109.476 no
C7 . O1 . C3 . 115(2) yes
C8 . O2 . C6 . 117.6(15) yes
C18 . N11 . C17 . 120(3) yes
C18 . N11 . O11 . 112(3) yes
C17 . N11 . O11 . 122(4) yes
C19 . N12 . O12 . 118.0(20) yes
C19 . N12 . C17 . 115(2) yes
O12 . N12 . C17 . 127(2) yes
N31 . O31 . O311 . 72.7(18) yes
N31 . O31 . N311 . 26.9(14) yes
O311 . O31 . N311 . 45.9(13) yes
N32 . O32 . O321 . 64.5(13) yes
N32 . O32 . N321 . 22.7(11) yes
O321 . O32 . N321 . 41.8(10) yes
C38 . N31 . C37 . 110(2) yes
C38 . N31 . O31 . 124(2) yes
C37 . N31 . O31 . 125(2) yes
C38 . N31 . O311 . 104.9(20) yes
C37 . N31 . O311 . 102.9(17) yes
O31 . N31 . O311 . 58.1(16) yes
C38 . N31 . N311 . 82(3) yes
C37 . N31 . N311 . 73(2) yes
O31 . N31 . N311 . 106(3) yes
O311 . N31 . N311 . 48(2) yes
C39 . N32 . C37 . 104.8(18) yes
C39 . N32 . O32 . 124.7(17) yes
C37 . N32 . O32 . 130.5(19) yes
C39 . N32 . O321 . 98.4(16) yes
C37 . N32 . O321 . 102.4(17) yes
O32 . N32 . O321 . 72.9(13) yes
C39 . N32 . N321 . 71(2) yes
C37 . N32 . N321 . 73(2) yes
O32 . N32 . N321 . 121(3) yes
O321 . N32 . N321 . 48.3(19) yes
N31 . O311 . O31 . 49.2(13) yes
N31 . O311 . N311 . 28.3(15) yes
O31 . O311 . N311 . 77.4(19) yes
N32 . O321 . O32 . 42.6(9) yes
N32 . O321 . N321 . 28.6(12) yes
O32 . O321 . N321 . 71.2(14) yes
C38 . N311 . O31 . 97.3(19) yes
C38 . N311 . C37 . 106(2) yes
O31 . N311 . C37 . 101(2) yes
C38 . N311 . O311 . 122(2) yes
O31 . N311 . O311 . 56.7(16) yes
C37 . N311 . O311 . 128(2) yes
C38 . N311 . N31 . 68(2) yes
O31 . N311 . N31 . 47(2) yes
C37 . N311 . N31 . 74(3) yes
O311 . N311 . N31 . 104(3) yes
C39 . N321 . C37 . 107.8(19) yes
C39 . N321 . O32 . 96.3(15) yes
C37 . N321 . O32 . 96.0(16) yes
C39 . N321 . O321 . 122.9(20) yes
C37 . N321 . O321 . 127(2) yes
O32 . N321 . O321 . 67.0(14) yes
C39 . N321 . N32 . 78(2) yes
C37 . N321 . N32 . 73(2) yes
O32 . N321 . N32 . 36.0(17) yes
O321 . N321 . N32 . 103(3) yes


_database_code_depnum_ccdc_archive 'CCDC 822066'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_baumgarten_diac
#TrackingRef '4558_web_deposit_cif_file_3_YuliaBorozdina_1299676307.cif'

_audit_creation_date             08-06-30
_audit_creation_method           CRYSTALS_ver_12.39

_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   8.1768(2)
_cell_length_b                   19.0191(8)
_cell_length_c                   8.6983(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.400(2)
_cell_angle_gamma                90
_cell_volume                     1315.89(8)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
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'
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'
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'


_cell_formula_units_Z            4

# Given Formula = C15 H14 N2 O2
# Dc = 1.28 Fooo = 544.00 Mu = 0.87 M = 254.29
# Found Formula = C15 H16 N2 O2
# Dc = 1.29 FOOO = 544.00 Mu = 0.87 M = 256.30

_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_compound_source        ?
_chemical_formula_weight         256.30


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    120

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark blue'
_exptl_crystal_size_min          0.13
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_max          0.41

_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.087

# Sheldrick geometric approximatio 0.97 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1996)'
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1996)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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      120
_diffrn_reflns_number            14007
_reflns_number_total             3687
_diffrn_reflns_av_R_equivalents  0.091
# Number of reflections with Friedels Law is 3687
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3696


_diffrn_reflns_theta_min         2.142
_diffrn_reflns_theta_max         29.602
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        29.602
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              26
_reflns_limit_l_min              0
_reflns_limit_l_max              12


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

_refine_diff_density_min         -0.41
_refine_diff_density_max         0.54


_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_number_parameters     173

#_refine_ls_R_factor_ref 0.0732
_refine_ls_wR_factor_ref         0.0724
_refine_ls_goodness_of_fit_ref   0.9848

#_reflns_number_all 3679
_refine_ls_R_factor_all          0.1048
_refine_ls_wR_factor_all         0.0786

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                2221
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_gt          0.0724

_refine_ls_shift/su_max          0.082527

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


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, 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:
4.29 1.80 3.72
;

# 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
O18 O 0.1241(2) 0.28024(9) 0.0477(2) 0.0377 1.0000 Uani . . . . . .
N16 N 0.1990(2) 0.22256(9) 0.0339(2) 0.0237 1.0000 Uani . . . . . .
O19 O 0.5261(2) 0.11929(9) -0.0221(2) 0.0385 1.0000 Uani . . . . . .
C6 C 0.4716(2) 0.27345(10) 0.0063(2) 0.0216 1.0000 Uani . . . . . .
C4 C 0.5712(3) 0.39095(11) 0.0806(3) 0.0295 1.0000 Uani . . . . . .
C2 C 0.8239(3) 0.43558(11) 0.0002(2) 0.0272 1.0000 Uani . . . . . .
C1 C 0.9359(3) 0.47677(12) 0.0000(3) 0.0276 1.0000 Uani . . . . . .
N17 N 0.3889(2) 0.14614(9) -0.0020(2) 0.0247 1.0000 Uani . . . . . .
C10 C 0.1062(3) 0.15400(10) 0.0200(2) 0.0234 1.0000 Uani . . . . . .
C9 C 0.3560(2) 0.21559(10) 0.0127(2) 0.0209 1.0000 Uani . . . . . .
C7 C 0.6010(3) 0.26496(11) -0.0742(3) 0.0272 1.0000 Uani . . . . . .
C8 C 0.7123(3) 0.31897(12) -0.0775(3) 0.0302 1.0000 Uani . . . . . .
C5 C 0.4572(3) 0.33761(11) 0.0812(3) 0.0283 1.0000 Uani . . . . . .
C3 C 0.7007(3) 0.38250(10) 0.0006(2) 0.0244 1.0000 Uani . . . . . .
C11 C 0.2512(3) 0.10021(11) 0.0286(3) 0.0252 1.0000 Uani . . . . . .
C13 C -0.0195(3) 0.15541(12) -0.1406(3) 0.0333 1.0000 Uani . . . . . .
C12 C 0.0116(4) 0.15010(13) 0.1508(3) 0.0395 1.0000 Uani . . . . . .
C15 C 0.3191(4) 0.07029(17) 0.1942(4) 0.0504 1.0000 Uani . . . . . .
C14 C 0.2159(3) 0.04152(14) -0.0917(4) 0.0475 1.0000 Uani . . . . . .
H41 H 0.5630 0.4338 0.1345 0.0380 1.0000 Uiso R . . . . .
H71 H 0.6114 0.2219 -0.1266 0.0362 1.0000 Uiso R . . . . .
H81 H 0.7987 0.3133 -0.1331 0.0407 1.0000 Uiso R . . . . .
H51 H 0.3681 0.3445 0.1330 0.0387 1.0000 Uiso R . . . . .
H131 H -0.0826 0.1130 -0.1556 0.0447 1.0000 Uiso R . . . . .
H132 H -0.0934 0.1942 -0.1441 0.0447 1.0000 Uiso R . . . . .
H133 H 0.0398 0.1601 -0.2219 0.0447 1.0000 Uiso R . . . . .
H121 H -0.0491 0.1071 0.1427 0.0497 1.0000 Uiso R . . . . .
H122 H -0.0645 0.1885 0.1414 0.0497 1.0000 Uiso R . . . . .
H123 H 0.0896 0.1522 0.2503 0.0497 1.0000 Uiso R . . . . .
H151 H 0.2379 0.0401 0.2218 0.0650 1.0000 Uiso R . . . . .
H152 H 0.3443 0.1076 0.2685 0.0650 1.0000 Uiso R . . . . .
H153 H 0.4186 0.0444 0.1948 0.0650 1.0000 Uiso R . . . . .
H141 H 0.1285 0.0126 -0.0714 0.0585 1.0000 Uiso R . . . . .
H142 H 0.3145 0.0141 -0.0845 0.0585 1.0000 Uiso R . . . . .
H143 H 0.1819 0.0610 -0.1948 0.0585 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       -10(80)
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'

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
O18 . N16 . 1.275(2) yes
N16 . C10 . 1.499(2) yes
N16 . C9 . 1.345(3) yes
O19 . N17 . 1.281(2) yes
C6 . C9 . 1.460(3) yes
C6 . C7 . 1.407(3) yes
C6 . C5 . 1.401(3) yes
C4 . C5 . 1.379(3) yes
C4 . C3 . 1.405(3) yes
C4 . H41 . 0.950 no
C2 . C1 . 1.206(3) yes
C2 . C3 . 1.426(3) yes
C1 . C1 2_765 1.371(4) yes
N17 . C9 . 1.360(3) yes
N17 . C11 . 1.497(3) yes
C10 . C11 . 1.554(3) yes
C10 . C13 . 1.531(3) yes
C10 . C12 . 1.518(3) yes
C7 . C8 . 1.377(3) yes
C7 . H71 . 0.950 no
C8 . C3 . 1.400(3) yes
C8 . H81 . 0.950 no
C5 . H51 . 0.950 no
C11 . C15 . 1.529(3) yes
C11 . C14 . 1.511(3) yes
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 no
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
C15 . H151 . 0.950 no
C15 . H152 . 0.950 no
C15 . H153 . 0.950 no
C14 . H141 . 0.950 no
C14 . H142 . 0.950 no
C14 . H143 . 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
O18 . N16 . C10 . 120.73(16) yes
O18 . N16 . C9 . 126.28(17) yes
C10 . N16 . C9 . 112.60(16) yes
C9 . C6 . C7 . 120.03(17) yes
C9 . C6 . C5 . 120.92(17) yes
C7 . C6 . C5 . 119.05(17) yes
C5 . C4 . C3 . 120.42(19) yes
C5 . C4 . H41 . 120.204 no
C3 . C4 . H41 . 119.379 no
C1 . C2 . C3 . 175.5(2) yes
C1 2_765 C1 . C2 . 179.6(3) yes
O19 . N17 . C9 . 126.76(17) yes
O19 . N17 . C11 . 120.67(17) yes
C9 . N17 . C11 . 112.16(16) yes
N16 . C10 . C11 . 101.70(15) yes
N16 . C10 . C13 . 106.16(16) yes
C11 . C10 . C13 . 113.49(17) yes
N16 . C10 . C12 . 108.56(17) yes
C11 . C10 . C12 . 116.57(19) yes
C13 . C10 . C12 . 109.5(2) yes
C6 . C9 . N17 . 125.79(17) yes
C6 . C9 . N16 . 125.29(18) yes
N17 . C9 . N16 . 108.92(16) yes
C6 . C7 . C8 . 120.11(19) yes
C6 . C7 . H71 . 119.888 no
C8 . C7 . H71 . 120.001 no
C7 . C8 . C3 . 120.95(19) yes
C7 . C8 . H81 . 119.871 no
C3 . C8 . H81 . 119.181 no
C6 . C5 . C4 . 120.58(19) yes
C6 . C5 . H51 . 119.759 no
C4 . C5 . H51 . 119.658 no
C2 . C3 . C4 . 122.26(19) yes
C2 . C3 . C8 . 118.86(19) yes
C4 . C3 . C8 . 118.85(17) yes
C10 . C11 . N17 . 101.77(15) yes
C10 . C11 . C15 . 113.4(2) yes
N17 . C11 . C15 . 105.10(18) yes
C10 . C11 . C14 . 115.58(19) yes
N17 . C11 . C14 . 109.83(19) yes
C15 . C11 . C14 . 110.3(2) yes
C10 . C13 . H131 . 109.793 no
C10 . C13 . H132 . 109.305 no
H131 . C13 . H132 . 109.476 no
C10 . C13 . H133 . 109.301 no
H131 . C13 . H133 . 109.476 no
H132 . C13 . H133 . 109.476 no
C10 . C12 . H121 . 109.565 no
C10 . C12 . H122 . 109.616 no
H121 . C12 . H122 . 109.476 no
C10 . C12 . H123 . 109.218 no
H121 . C12 . H123 . 109.476 no
H122 . C12 . H123 . 109.476 no
C11 . C15 . H151 . 109.900 no
C11 . C15 . H152 . 109.699 no
H151 . C15 . H152 . 109.476 no
C11 . C15 . H153 . 108.799 no
H151 . C15 . H153 . 109.476 no
H152 . C15 . H153 . 109.476 no
C11 . C14 . H141 . 109.290 no
C11 . C14 . H142 . 109.667 no
H141 . C14 . H142 . 109.476 no
C11 . C14 . H143 . 109.443 no
H141 . C14 . H143 . 109.476 no
H142 . C14 . H143 . 109.476 no
_database_code_depnum_ccdc_archive 'CCDC 816633'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dirad2_0310
#TrackingRef '4560_web_deposit_cif_file_5_YuliaBorozdina_1299676307.cif'


_audit_creation_date             10-03-31

_audit_creation_method           CRYSTALS_ver_12.84



_chemical_name_systematic        ?

_chemical_melting_point          ?



_cell_length_a                   6.0834(4)

_cell_length_b                   11.2581(5)

_cell_length_c                   19.1236(9)

_cell_angle_alpha                90

_cell_angle_beta                 90.832(3)

_cell_angle_gamma                90

_cell_volume                     1309.59(12)



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   'P 1 21/n 1 '

_symmetry_space_group_name_Hall  ?

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'
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'
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'





_cell_formula_units_Z            4



# Given Formula = C14 H16 N2 O2

# Dc = 1.24 Fooo = 520.00 Mu = 0.84 M = 244.29

# Found Formula = C14 H16 N2 O2

# Dc = 1.24 FOOO = 520.00 Mu = 0.84 M = 244.29



_chemical_formula_sum            'C14 H16 N2 O2'

_chemical_formula_moiety         'C14 H16 N2 O2'

_chemical_compound_source        ?

_chemical_formula_weight         244.29





_cell_measurement_reflns_used    0

_cell_measurement_theta_min      0

_cell_measurement_theta_max      0

_cell_measurement_temperature    120



_exptl_crystal_description       prism

_exptl_crystal_colour            'dark blue'

_exptl_crystal_size_min          0.21

_exptl_crystal_size_mid          0.24

_exptl_crystal_size_max          0.39



_exptl_crystal_density_diffrn    1.239

_exptl_crystal_density_meas      ?

# Non-dispersive F(000):

_exptl_crystal_F_000             520

_exptl_absorpt_coefficient_mu    0.084



# Sheldrick geometric approximatio 0.98 0.98

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   'SORTAV (Blessing)'

_exptl_absorpt_correction_T_min  0.81

_exptl_absorpt_correction_T_max  0.98

# For a Kappa CCD, set Tmin to 1.0 and

# Tmax to the ratio of max:min frame scales in scale_all.log

_diffrn_measurement_device_type  'Nonius KappaCCD'

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073

_diffrn_measurement_method       'φ & ω scans'



# If a reference occurs more than once, delete the author

# and date from subsequent references.

_computing_data_collection       'COLLECT (Nonius, 1997-2001).'

_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'

_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      120

_diffrn_reflns_number            9800

_reflns_number_total             3784

_diffrn_reflns_av_R_equivalents  0.046

# Number of reflections with Friedels Law is 3784

# Number of reflections without Friedels Law is 0

# Theoretical number of reflections is about 3987





_diffrn_reflns_theta_min         3.530

_diffrn_reflns_theta_max         30.493

_diffrn_measured_fraction_theta_max 0.947



_diffrn_reflns_theta_full        25.004

_diffrn_measured_fraction_theta_full 0.968





_diffrn_reflns_limit_h_min       -8

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -16

_diffrn_reflns_limit_k_max       16

_diffrn_reflns_limit_l_min       -27

_diffrn_reflns_limit_l_max       27

_reflns_limit_h_min              -8

_reflns_limit_h_max              8

_reflns_limit_k_min              0

_reflns_limit_k_max              16

_reflns_limit_l_min              0

_reflns_limit_l_max              27





_atom_sites_solution_primary     direct #heavy,direct,difmap,geom

# _atom_sites_solution_secondary difmap

_atom_sites_solution_hydrogens   geom



_refine_diff_density_min         -0.20

_refine_diff_density_max         0.37





_refine_ls_number_reflns         2480

_refine_ls_number_restraints     0

_refine_ls_number_parameters     163



#_refine_ls_R_factor_ref 0.0453

_refine_ls_wR_factor_ref         0.0550

_refine_ls_goodness_of_fit_ref   1.0812



#_reflns_number_all 3782

_refine_ls_R_factor_all          0.0739

_refine_ls_wR_factor_all         0.0592



# The I/u(I) cutoff below was used for refinement as

# well as the _gt R-factors:

_reflns_threshold_expression     I>3.0σ(I)

_reflns_number_gt                2480

_refine_ls_R_factor_gt           0.0453

_refine_ls_wR_factor_gt          0.0550



_refine_ls_shift/su_max          0.004943



# choose from: rm (reference molecule of known chirality),

# ad (anomolous dispersion - Flack), rmad (rm and ad),

# syn (from synthesis), unk (unknown) or . (not applicable).

_chemical_absolute_configuration .





_refine_ls_structure_factor_coef F

_refine_ls_matrix_type           full

_refine_ls_hydrogen_treatment    constr # none, 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:

2.23 0.979 1.76

;



# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3



# Replace last . with number of unfound hydrogen atomsattached 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 0.57807(19) 0.04470(10) 0.18802(6) 0.0244 1.0000 Uani . . . . . .
N2 N 0.36850(19) -0.07050(10) 0.12272(6) 0.0233 1.0000 Uani . . . . . .
C1 C 0.0414(2) 0.45623(13) 0.01254(7) 0.0282 1.0000 Uani . . . . . .
C2 C 0.1376(2) 0.35195(12) 0.04310(6) 0.0249 1.0000 Uani . . . . . .
C3 C 0.3502(2) 0.35632(12) 0.07281(7) 0.0259 1.0000 Uani . . . . . .
C4 C 0.4412(2) 0.25596(12) 0.10348(7) 0.0244 1.0000 Uani . . . . . .
C5 C 0.3234(2) 0.14880(11) 0.10461(6) 0.0222 1.0000 Uani . . . . . .
C6 C 0.1123(2) 0.14428(12) 0.07384(7) 0.0244 1.0000 Uani . . . . . .
C7 C 0.0215(2) 0.24501(13) 0.04356(6) 0.0258 1.0000 Uani . . . . . .
C8 C 0.4207(2) 0.04403(12) 0.13756(6) 0.0215 1.0000 Uani . . . . . .
C9 C 0.6231(2) -0.07659(11) 0.21692(7) 0.0234 1.0000 Uani . . . . . .
C10 C 0.8695(2) -0.08994(14) 0.22899(8) 0.0290 1.0000 Uani . . . . . .
C11 C 0.5029(3) -0.08314(15) 0.28664(7) 0.0345 1.0000 Uani . . . . . .
C12 C 0.5212(2) -0.15695(12) 0.15876(7) 0.0248 1.0000 Uani . . . . . .
C13 C 0.6852(3) -0.19510(15) 0.10348(8) 0.0364 1.0000 Uani . . . . . .
C14 C 0.3929(3) -0.26367(13) 0.18428(9) 0.0360 1.0000 Uani . . . . . .
O1 O 0.6659(2) 0.13616(10) 0.21650(6) 0.0414 1.0000 Uani . . . . . .
O2 O 0.22862(18) -0.10611(10) 0.07688(6) 0.0347 1.0000 Uani . . . . . .
H31 H 0.4313 0.4284 0.0719 0.0348 1.0000 Uiso R . . . . .
H41 H 0.5839 0.2596 0.1242 0.0332 1.0000 Uiso R . . . . .
H61 H 0.0327 0.0717 0.0737 0.0336 1.0000 Uiso R . . . . .
H71 H -0.1215 0.2414 0.0230 0.0344 1.0000 Uiso R . . . . .
H101 H 0.9006 -0.1663 0.2478 0.0404 1.0000 Uiso R . . . . .
H102 H 0.9199 -0.0307 0.2608 0.0404 1.0000 Uiso R . . . . .
H103 H 0.9421 -0.0810 0.1857 0.0404 1.0000 Uiso R . . . . .
H111 H 0.5272 -0.1588 0.3073 0.0466 1.0000 Uiso R . . . . .
H112 H 0.5576 -0.0230 0.3171 0.0466 1.0000 Uiso R . . . . .
H113 H 0.3498 -0.0717 0.2789 0.0466 1.0000 Uiso R . . . . .
H131 H 0.7863 -0.2503 0.1234 0.0485 1.0000 Uiso R . . . . .
H132 H 0.7627 -0.1275 0.0873 0.0485 1.0000 Uiso R . . . . .
H133 H 0.6087 -0.2313 0.0654 0.0485 1.0000 Uiso R . . . . .
H141 H 0.4903 -0.3179 0.2068 0.0484 1.0000 Uiso R . . . . .
H142 H 0.2854 -0.2379 0.2165 0.0484 1.0000 Uiso R . . . . .
H143 H 0.3225 -0.3018 0.1457 0.0484 1.0000 Uiso R . . . . .




_refine_ls_extinction_method     None

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 . C8 . 1.3496(15) yes
N1 . C9 . 1.4969(16) yes
N1 . O1 . 1.2782(15) yes
N2 . C8 . 1.3569(16) yes
N2 . C12 . 1.5057(16) yes
N2 . O2 . 1.2774(14) yes
C1 . C1 2_565 1.203(3) yes
C1 . C2 . 1.4325(19) yes
C2 . C3 . 1.4059(19) yes
C2 . C7 . 1.396(2) yes
C3 . C4 . 1.3847(18) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.4035(18) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.4057(17) yes
C5 . C8 . 1.4586(17) yes
C6 . C7 . 1.3847(18) yes
C6 . H61 . 0.950 no
C7 . H71 . 0.950 no
C9 . C10 . 1.5207(18) yes
C9 . C11 . 1.5317(19) yes
C9 . C12 . 1.5555(18) yes
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C10 . H103 . 0.950 no
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C11 . H113 . 0.950 no
C12 . C13 . 1.526(2) yes
C12 . C14 . 1.517(2) yes
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 no
C14 . H141 . 0.950 no
C14 . H142 . 0.950 no
C14 . H143 . 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
































































C8 . N1 . C9 . 112.52(11) yes
C8 . N1 . O1 . 126.65(11) yes
C9 . N1 . O1 . 120.29(10) yes
C8 . N2 . C12 . 112.19(10) yes
C8 . N2 . O2 . 126.38(11) yes
C12 . N2 . O2 . 120.78(11) yes
C1 2_565 C1 . C2 . 179.20(19) yes
C1 . C2 . C3 . 120.27(13) yes
C1 . C2 . C7 . 120.38(12) yes
C3 . C2 . C7 . 119.35(12) yes
C2 . C3 . C4 . 120.15(13) yes
C2 . C3 . H31 . 119.8 no
C4 . C3 . H31 . 120.1 no
C3 . C4 . C5 . 120.47(12) yes
C3 . C4 . H41 . 119.9 no
C5 . C4 . H41 . 119.6 no
C4 . C5 . C6 . 119.21(12) yes
C4 . C5 . C8 . 119.86(11) yes
C6 . C5 . C8 . 120.93(12) yes
C5 . C6 . C7 . 120.13(12) yes
C5 . C6 . H61 . 119.7 no
C7 . C6 . H61 . 120.2 no
C2 . C7 . C6 . 120.67(12) yes
C2 . C7 . H71 . 119.6 no
C6 . C7 . H71 . 119.7 no
C5 . C8 . N2 . 125.87(11) yes
C5 . C8 . N1 . 125.70(12) yes
N2 . C8 . N1 . 108.43(11) yes
N1 . C9 . C10 . 108.71(11) yes
N1 . C9 . C11 . 106.15(11) yes
C10 . C9 . C11 . 110.20(11) yes
N1 . C9 . C12 . 101.40(9) yes
C10 . C9 . C12 . 115.63(11) yes
C11 . C9 . C12 . 113.84(11) yes
C9 . C10 . H101 . 109.7 no
C9 . C10 . H102 . 109.6 no
H101 . C10 . H102 . 109.5 no
C9 . C10 . H103 . 109.1 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no
C9 . C11 . H111 . 109.4 no
C9 . C11 . H112 . 109.3 no
H111 . C11 . H112 . 109.5 no
C9 . C11 . H113 . 109.7 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
C9 . C12 . N2 . 100.84(10) yes
C9 . C12 . C13 . 113.68(11) yes
N2 . C12 . C13 . 105.67(11) yes
C9 . C12 . C14 . 115.59(12) yes
N2 . C12 . C14 . 110.01(11) yes
C13 . C12 . C14 . 110.15(13) yes
C12 . C13 . H131 . 109.4 no
C12 . C13 . H132 . 109.5 no
H131 . C13 . H132 . 109.5 no
C12 . C13 . H133 . 109.5 no
H131 . C13 . H133 . 109.5 no
H132 . C13 . H133 . 109.5 no
C12 . C14 . H141 . 109.6 no
C12 . C14 . H142 . 109.2 no
H141 . C14 . H142 . 109.5 no
C12 . C14 . H143 . 109.6 no
H141 . C14 . H143 . 109.5 no
H142 . C14 . H143 . 109.5 no


_database_code_depnum_ccdc_archive 'CCDC 816635'
