# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

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

data_4_H2O
_database_code_depnum_ccdc_archive 'CCDC 1834203'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_audit_creation_date             2018-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C15 H20 N3 O, H2 O'
_chemical_formula_sum            'C15 H22 Br N3 O2'
_chemical_formula_weight         356.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N3 O Br C15'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.56160(10)
_cell_length_b                   14.0149(4)
_cell_length_c                   20.3191(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1583.78(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6912
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.1000
_cell_measurement_theta_min      3.8010
_shelx_estimated_absorpt_T_max   0.714
_shelx_estimated_absorpt_T_min   0.563
_exptl_absorpt_coefficient_mu    3.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11976
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.260
_diffrn_reflns_theta_min         3.832
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  64.00   1.00    1.00    --   40.38 -38.00 120.00   35
  2  ω     81.00 106.00   1.00    1.03    --  113.00 -95.00 120.00   25
  3  ω     62.00  96.00   1.00    1.03    --  113.00 -77.00 150.00   34
  4  ω     48.00  74.00   1.00    1.03    --  113.00 -95.00 120.00   26
  5  ω     46.00 115.00   1.00    1.03    --  113.00-112.00 120.00   69
  6  ω     43.00 144.00   1.00    1.03    --  113.00 -30.00 -30.00  101
  7  ω     95.00 120.00   1.00    1.03    --  113.00  45.00-180.00   25
  8  ω    138.00 163.00   1.00    1.03    --  113.00  45.00-180.00   25
  9  ω     69.00 117.00   1.00    1.03    --  113.00 178.00 -90.00   48
 10  ω    115.00 177.00   1.00    1.03    --  113.00 112.00  60.00   62
 11  ω    105.00 130.00   1.00    1.03    --  113.00 114.00 168.00   25
 12  ω     55.00  80.00   1.00    1.03    --  113.00 -95.00 -30.00   25
 13  ω      8.00  34.00   1.00    1.00    --   40.38 -99.00 -60.00   26
 14  ω    -70.00  34.00   1.00    1.00    --  -40.38  57.00  30.00  104
 15  ω      7.00  33.00   1.00    1.00    --   40.38 -99.00 120.00   26
 16  ω     41.00  72.00   1.00    1.00    --   40.38 -99.00 120.00   31
 17  ω     34.00  73.00   1.00    1.00    --   40.38 -99.00 -60.00   39
 18  ω     36.00  64.00   1.00    1.03    --  113.00 -95.00-180.00   28
 19  ω     95.00 121.00   1.00    1.03    --  113.00 -77.00 -60.00   26
 20  ω     90.00 116.00   1.00    1.03    --  113.00 178.00-150.00   26
 21  ω     52.00  91.00   1.00    1.03    --  113.00 -30.00 120.00   39
 22  ω     38.00  80.00   1.00    1.03    --  113.00 -95.00 150.00   42
 23  ω     57.00  86.00   1.00    1.03    --  113.00 178.00  90.00   29
 24  ω    121.00 147.00   1.00    1.03    --  113.00 178.00  90.00   26
 25  ω     46.00  90.00   1.00    1.03    --  113.00 -45.00 -90.00   44
 26  ω    102.00 135.00   1.00    1.03    --  113.00 112.00 -30.00   33
 27  ω    -73.00 -34.00   1.00    1.00    --  -40.38 178.00-180.00   39
 28  ω    105.00 130.00   1.00    1.00    --   40.38 178.00-120.00   25
 29  ω     63.00 101.00   1.00    1.03    --  113.00 -95.00  30.00   38
 30  ω     42.00  68.00   1.00    1.03    --  113.00 -45.00-180.00   26
 31  ω    140.00 168.00   1.00    1.03    --  113.00   0.00-180.00   28
 32  ω     45.00  86.00   1.00    1.03    --  113.00   0.00-180.00   41
 33  ω     84.00 109.00   1.00    1.03    --  113.00 178.00   0.00   25
 34  ω     60.00  85.00   1.00    1.03    --  113.00 -95.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1469845000
_diffrn_orient_matrix_UB_12      0.0594622000
_diffrn_orient_matrix_UB_13      -0.0494307000
_diffrn_orient_matrix_UB_21      0.0484794000
_diffrn_orient_matrix_UB_22      -0.0904707000
_diffrn_orient_matrix_UB_23      -0.0409611000
_diffrn_orient_matrix_UB_31      -0.2297679000
_diffrn_orient_matrix_UB_32      0.0189784000
_diffrn_orient_matrix_UB_33      -0.0403302000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3164
_reflns_number_total             3290
_reflns_odcompleteness_completeness 95.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.092(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0234
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0596
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.908(19)
 0.092(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Riding coordinates:
 C12(H1SA,H1SB)
3.b Ternary CH refined with riding coordinates:
 C9(H9)
3.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B)
3.d Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C4(H4), C5(H5), C8(H8), C7(H7)
3.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.40803(5) 0.56557(2) 0.23841(2) 0.01644(9) Uani 1 1 d . . . . .
O1 O 0.8282(3) 0.44765(16) 0.32596(10) 0.0138(4) Uani 1 1 d . . . . .
O1S O 0.0951(5) 0.15113(18) 0.33626(11) 0.0243(5) Uani 1 1 d . . . . .
N2 N 0.6566(4) 0.52872(19) 0.40935(12) 0.0131(5) Uani 1 1 d . . . . .
N3 N 0.9923(5) 0.59231(19) 0.35126(13) 0.0157(5) Uani 1 1 d . . . . .
H3 H 1.1068 0.5776 0.3247 0.019 Uiso 1 1 calc R . . . .
N1 N 0.6361(4) 0.39499(19) 0.35192(13) 0.0138(5) Uani 1 1 d . . . . .
C2 C 0.8278(5) 0.5284(2) 0.36358(14) 0.0139(6) Uani 1 1 d . . . . .
C3 C 0.3394(5) 0.4156(2) 0.44208(15) 0.0138(6) Uani 1 1 d . . . . .
C6 C -0.0342(5) 0.3674(2) 0.52730(15) 0.0170(6) Uani 1 1 d . . . . .
H6 H -0.1602 0.3516 0.5553 0.020 Uiso 1 1 calc R . . . .
C1 C 0.5414(5) 0.4456(2) 0.40032(13) 0.0129(6) Uani 1 1 d . . . . .
C4 C 0.1738(5) 0.3457(2) 0.42404(15) 0.0139(6) Uani 1 1 d . . . . .
H4 H 0.1870 0.3151 0.3836 0.017 Uiso 1 1 calc R . . . .
C9 C 0.9914(5) 0.6883(2) 0.38062(15) 0.0143(6) Uani 1 1 d . . . . .
H9 H 0.8743 0.6895 0.4166 0.017 Uiso 1 1 calc R . . . .
C5 C -0.0113(5) 0.3219(2) 0.46704(15) 0.0167(6) Uani 1 1 d . . . . .
H5 H -0.1211 0.2749 0.4552 0.020 Uiso 1 1 calc R . . . .
C8 C 0.3184(6) 0.4608(2) 0.50347(15) 0.0164(6) Uani 1 1 d . . . . .
H8 H 0.4298 0.5069 0.5159 0.020 Uiso 1 1 calc R . . . .
C14 C 0.9159(7) 0.7607(2) 0.32893(15) 0.0210(6) Uani 1 1 d . . . . .
H14A H 0.7516 0.7479 0.3155 0.025 Uiso 1 1 calc R . . . .
H14B H 1.0181 0.7542 0.2905 0.025 Uiso 1 1 calc R . . . .
C10 C 1.2407(6) 0.7098(2) 0.40873(17) 0.0199(7) Uani 1 1 d . . . . .
H10A H 1.2751 0.6659 0.4444 0.024 Uiso 1 1 calc R . . . .
H10B H 1.3610 0.7004 0.3748 0.024 Uiso 1 1 calc R . . . .
C7 C 0.1317(5) 0.4368(3) 0.54582(14) 0.0175(6) Uani 1 1 d . . . . .
H7 H 0.1176 0.4670 0.5864 0.021 Uiso 1 1 calc R . . . .
C11 C 1.2550(6) 0.8122(3) 0.43425(17) 0.0216(7) Uani 1 1 d . . . . .
H11A H 1.1480 0.8195 0.4716 0.026 Uiso 1 1 calc R . . . .
H11B H 1.4175 0.8254 0.4490 0.026 Uiso 1 1 calc R . . . .
C15 C 0.6047(6) 0.3024(2) 0.32135(15) 0.0207(6) Uani 1 1 d . . . . .
H15A H 0.5081 0.3090 0.2825 0.031 Uiso 1 1 calc GR . . . .
H15B H 0.5263 0.2600 0.3517 0.031 Uiso 1 1 calc GR . . . .
H15C H 0.7590 0.2768 0.3097 0.031 Uiso 1 1 calc GR . . . .
C13 C 0.9335(7) 0.8627(2) 0.35525(18) 0.0249(7) Uani 1 1 d . . . . .
H13A H 0.8950 0.9074 0.3204 0.030 Uiso 1 1 calc R . . . .
H13B H 0.8178 0.8715 0.3905 0.030 Uiso 1 1 calc R . . . .
C12 C 1.1855(6) 0.8829(2) 0.38097(17) 0.0232(7) Uani 1 1 d . . . . .
H12A H 1.2997 0.8789 0.3450 0.028 Uiso 1 1 calc R . . . .
H12B H 1.1918 0.9472 0.3987 0.028 Uiso 1 1 calc R . . . .
H1SA H 0.2138 0.1329 0.3131 0.028 Uiso 1 1 d R . . . .
H1SB H -0.0288 0.1190 0.3256 0.028 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.402(3) . ?
O1 C2 1.366(4) . ?
O1S H1SA 0.8503 . ?
O1S H1SB 0.8515 . ?
N2 C2 1.331(4) . ?
N2 C1 1.342(4) . ?
N3 H3 0.8600 . ?
N3 C2 1.304(4) . ?
N3 C9 1.472(4) . ?
N1 C1 1.322(4) . ?
N1 C15 1.449(4) . ?
C3 C1 1.470(4) . ?
C3 C4 1.394(4) . ?
C3 C8 1.404(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.386(4) . ?
C6 C7 1.392(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(4) . ?
C9 H9 0.9800 . ?
C9 C14 1.520(4) . ?
C9 C10 1.529(4) . ?
C5 H5 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.390(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.530(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.527(5) . ?
C7 H7 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.518(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.522(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 N1 103.0(2) . . ?
H1SA O1S H1SB 109.2 . . ?
C2 N2 C1 104.1(3) . . ?
C2 N3 H3 118.4 . . ?
C2 N3 C9 123.2(3) . . ?
C9 N3 H3 118.4 . . ?
O1 N1 C15 113.7(2) . . ?
C1 N1 O1 107.5(2) . . ?
C1 N1 C15 138.7(3) . . ?
N2 C2 O1 113.3(3) . . ?
N3 C2 O1 117.4(3) . . ?
N3 C2 N2 129.3(3) . . ?
C4 C3 C1 123.7(3) . . ?
C4 C3 C8 119.7(3) . . ?
C8 C3 C1 116.6(3) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
N2 C1 C3 122.3(3) . . ?
N1 C1 N2 112.2(3) . . ?
N1 C1 C3 125.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
N3 C9 H9 108.7 . . ?
N3 C9 C14 109.3(2) . . ?
N3 C9 C10 109.2(2) . . ?
C14 C9 H9 108.7 . . ?
C14 C9 C10 112.2(3) . . ?
C10 C9 H9 108.7 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C3 C8 H8 119.9 . . ?
C7 C8 C3 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C14 H14A 109.3 . . ?
C9 C14 H14B 109.3 . . ?
C9 C14 C13 111.4(3) . . ?
H14A C14 H14B 108.0 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.0(3) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 C10 111.0(3) . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C12 C13 C14 110.7(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C11 C12 C13 111.0(3) . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.265
_oxdiff_exptl_absorpt_empirical_full_min 0.856
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.908(19)
2 0.092(19)

####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1834207'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_audit_creation_date             2018-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N4'
_chemical_formula_sum            'C21 H22 N4'
_chemical_formula_weight         330.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.2501(8)
_cell_length_b                   12.7520(10)
_cell_length_c                   13.2943(10)
_cell_angle_alpha                86.090(6)
_cell_angle_beta                 89.456(6)
_cell_angle_gamma                67.095(7)
_cell_volume                     1752.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2641
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2650
_cell_measurement_theta_min      3.4860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15832
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.514
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00   47.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678   57.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -82.00  -50.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -57.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -38.00   48.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678   77.0000    0.0000 86

#__ type_ start__ end____ width___ exp.time_
  4 omega  -89.00  -36.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678 -178.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   20.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega   25.00   60.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega    5.00   92.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
  8 omega  -35.00   40.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -77.0000  150.0000 75
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0156964000
_diffrn_orient_matrix_UB_12      0.0384475000
_diffrn_orient_matrix_UB_13      -0.0435850000
_diffrn_orient_matrix_UB_21      0.0318422000
_diffrn_orient_matrix_UB_22      0.0316030000
_diffrn_orient_matrix_UB_23      0.0215755000
_diffrn_orient_matrix_UB_31      0.0585325000
_diffrn_orient_matrix_UB_32      -0.0344558000
_diffrn_orient_matrix_UB_33      -0.0222653000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5434
_reflns_number_total             7989
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.2403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C16A(H16A), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17A(H17A,H17B), C21A(H21A,H21B), C20A(H20A,H20B), C18A(H18A,H18B), C19A(H19A,
 H19B), C17(H17C,H17D), C18(H18C,H18D), C21(H21C,H21D), C19(H19C,H19D),
 C20(H20C,H20D)
2.c Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C12A(H12A), C6A(H6A), C15A(H15A), C13A(H13A), C9A(H9A), N4A(H4A),
 C7A(H7A), C5A(H5A), C8A(H8A), C14A(H14A), N4(H4), C9(H9), C11(H11), C7(H7),
 C14(H14), C5(H5), C13(H13), C12(H12), C15(H15), C6(H6), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4A C 0.39642(16) 1.05628(16) 0.10158(12) 0.0162(4) Uani 1 1 d . . . . .
N3A N 0.74567(13) 1.00139(13) 0.24699(10) 0.0159(3) Uani 1 1 d . . . . .
C2A C 0.71077(16) 0.91595(16) 0.22859(11) 0.0140(4) Uani 1 1 d . . . . .
C11A C 0.79166(17) 0.70362(16) 0.22581(12) 0.0182(4) Uani 1 1 d . . . . .
H11A H 0.7206 0.7127 0.1857 0.022 Uiso 1 1 calc R . . . .
N2A N 0.59786(13) 0.92658(13) 0.18557(10) 0.0153(3) Uani 1 1 d . . . . .
C12A C 0.88174(17) 0.59467(17) 0.25307(13) 0.0225(4) Uani 1 1 d . . . . .
H12A H 0.8705 0.5313 0.2312 0.027 Uiso 1 1 calc R . . . .
C1A C 0.52006(16) 1.03534(16) 0.15591(12) 0.0151(4) Uani 1 1 d . . . . .
C6A C 0.19702(17) 1.18989(18) 0.02239(13) 0.0231(4) Uani 1 1 d . . . . .
H6A H 0.1407 1.2647 0.0054 0.028 Uiso 1 1 calc R . . . .
N1A N 0.54453(13) 1.12719(13) 0.16977(10) 0.0157(3) Uani 1 1 d . . . . .
C15A C 0.91562(17) 0.78370(17) 0.31695(12) 0.0189(4) Uani 1 1 d . . . . .
H15A H 0.9280 0.8469 0.3379 0.023 Uiso 1 1 calc R . . . .
C13A C 0.98873(17) 0.57987(17) 0.31292(13) 0.0228(4) Uani 1 1 d . . . . .
H13A H 1.0486 0.5069 0.3316 0.027 Uiso 1 1 calc R . . . .
C9A C 0.36584(17) 0.96639(17) 0.07277(12) 0.0180(4) Uani 1 1 d . . . . .
H9A H 0.4223 0.8914 0.0887 0.022 Uiso 1 1 calc R . . . .
C17A C 0.78719(17) 1.30159(17) 0.32502(13) 0.0213(4) Uani 1 1 d . . . . .
H17A H 0.7248 1.3144 0.3784 0.026 Uiso 1 1 calc R . . . .
H17B H 0.7527 1.3643 0.2739 0.026 Uiso 1 1 calc R . . . .
C16A C 0.80640(16) 1.19017(16) 0.27880(12) 0.0163(4) Uani 1 1 d . . . . .
H16A H 0.8345 1.1287 0.3325 0.020 Uiso 1 1 calc R . . . .
C3A C 0.65792(16) 1.10667(16) 0.21814(12) 0.0149(4) Uani 1 1 d . . . . .
N4A N 0.68377(13) 1.19718(13) 0.23717(10) 0.0170(3) Uani 1 1 d . . . . .
H4A H 0.6244 1.2639 0.2241 0.020 Uiso 1 1 calc R . . . .
C21A C 0.91052(16) 1.16249(17) 0.19902(13) 0.0213(4) Uani 1 1 d . . . . .
H21A H 0.9239 1.0896 0.1729 0.026 Uiso 1 1 calc R . . . .
H21B H 0.8830 1.2206 0.1435 0.026 Uiso 1 1 calc R . . . .
C20A C 1.03584(17) 1.15757(18) 0.24484(14) 0.0236(4) Uani 1 1 d . . . . .
H20A H 1.1015 1.1406 0.1937 0.028 Uiso 1 1 calc R . . . .
H20B H 1.0653 1.0970 0.2982 0.028 Uiso 1 1 calc R . . . .
C7A C 0.16722(17) 1.09951(19) -0.00491(13) 0.0231(4) Uani 1 1 d . . . . .
H7A H 0.0908 1.1138 -0.0401 0.028 Uiso 1 1 calc R . . . .
C18A C 0.91329(17) 1.30010(18) 0.36794(14) 0.0240(4) Uani 1 1 d . . . . .
H18A H 0.9424 1.2441 0.4250 0.029 Uiso 1 1 calc R . . . .
H18B H 0.8991 1.3743 0.3915 0.029 Uiso 1 1 calc R . . . .
C5A C 0.31097(17) 1.16823(17) 0.07510(12) 0.0201(4) Uani 1 1 d . . . . .
H5A H 0.3308 1.2289 0.0930 0.024 Uiso 1 1 calc R . . . .
C8A C 0.25116(17) 0.98847(18) 0.02028(12) 0.0212(4) Uani 1 1 d . . . . .
H8A H 0.2309 0.9281 0.0021 0.025 Uiso 1 1 calc R . . . .
C14A C 1.00517(17) 0.67472(17) 0.34437(13) 0.0213(4) Uani 1 1 d . . . . .
H14A H 1.0766 0.6654 0.3841 0.026 Uiso 1 1 calc R . . . .
C19A C 1.01665(18) 1.27065(18) 0.28735(15) 0.0269(5) Uani 1 1 d . . . . .
H19A H 0.9911 1.3306 0.2333 0.032 Uiso 1 1 calc R . . . .
H19B H 1.0974 1.2660 0.3165 0.032 Uiso 1 1 calc R . . . .
C10A C 0.80676(16) 0.79919(16) 0.25799(12) 0.0149(4) Uani 1 1 d . . . . .
N1 N 0.42893(13) 0.59877(13) 0.30758(10) 0.0167(3) Uani 1 1 d . . . . .
N4 N 0.47211(13) 0.75970(13) 0.27914(10) 0.0169(3) Uani 1 1 d . . . . .
H4 H 0.5086 0.7980 0.2447 0.020 Uiso 1 1 calc R . . . .
C4 C 0.38803(16) 0.42932(16) 0.33980(12) 0.0159(4) Uani 1 1 d . . . . .
N3 N 0.56001(13) 0.61751(13) 0.16984(10) 0.0161(3) Uani 1 1 d . . . . .
N2 N 0.51428(13) 0.44993(13) 0.19598(10) 0.0149(3) Uani 1 1 d . . . . .
C1 C 0.44620(16) 0.49713(16) 0.27657(12) 0.0155(4) Uani 1 1 d . . . . .
C3 C 0.48707(16) 0.65671(16) 0.25134(12) 0.0155(4) Uani 1 1 d . . . . .
C10 C 0.65423(16) 0.46453(16) 0.06008(12) 0.0169(4) Uani 1 1 d . . . . .
C2 C 0.56992(16) 0.51475(16) 0.14644(12) 0.0149(4) Uani 1 1 d . . . . .
C17 C 0.25126(16) 0.85796(17) 0.34150(12) 0.0191(4) Uani 1 1 d . . . . .
H17C H 0.2269 0.7981 0.3192 0.023 Uiso 1 1 calc R . . . .
H17D H 0.2315 0.9174 0.2873 0.023 Uiso 1 1 calc R . . . .
C9 C 0.37598(16) 0.33400(17) 0.30454(14) 0.0198(4) Uani 1 1 d . . . . .
H9 H 0.4016 0.3135 0.2396 0.024 Uiso 1 1 calc R . . . .
C11 C 0.65255(17) 0.36845(16) 0.01781(12) 0.0180(4) Uani 1 1 d . . . . .
H11 H 0.5967 0.3352 0.0423 0.022 Uiso 1 1 calc R . . . .
C7 C 0.28446(18) 0.30095(19) 0.46116(15) 0.0279(5) Uani 1 1 d . . . . .
H7 H 0.2487 0.2585 0.5012 0.033 Uiso 1 1 calc R . . . .
C18 C 0.17438(17) 0.90729(18) 0.43493(13) 0.0224(4) Uani 1 1 d . . . . .
H18C H 0.0835 0.9439 0.4167 0.027 Uiso 1 1 calc R . . . .
H18D H 0.1849 0.8456 0.4854 0.027 Uiso 1 1 calc R . . . .
C21 C 0.43614(17) 0.90023(17) 0.40441(13) 0.0192(4) Uani 1 1 d . . . . .
H21C H 0.4180 0.9625 0.3530 0.023 Uiso 1 1 calc R . . . .
H21D H 0.5282 0.8681 0.4189 0.023 Uiso 1 1 calc R . . . .
C14 C 0.81870(19) 0.4672(2) -0.05696(14) 0.0296(5) Uani 1 1 d . . . . .
H14 H 0.8742 0.5004 -0.0822 0.036 Uiso 1 1 calc R . . . .
C5 C 0.34785(17) 0.46014(18) 0.43728(13) 0.0224(4) Uani 1 1 d . . . . .
H5 H 0.3559 0.5237 0.4618 0.027 Uiso 1 1 calc R . . . .
C19 C 0.21772(17) 0.99356(17) 0.47976(13) 0.0212(4) Uani 1 1 d . . . . .
H19C H 0.1733 1.0161 0.5425 0.025 Uiso 1 1 calc R . . . .
H19D H 0.1940 1.0611 0.4337 0.025 Uiso 1 1 calc R . . . .
C16 C 0.39577(16) 0.80946(16) 0.36610(12) 0.0165(4) Uani 1 1 d . . . . .
H16 H 0.4133 0.7487 0.4200 0.020 Uiso 1 1 calc R . . . .
C13 C 0.81732(18) 0.37045(19) -0.09764(13) 0.0274(5) Uani 1 1 d . . . . .
H13 H 0.8726 0.3384 -0.1497 0.033 Uiso 1 1 calc R . . . .
C12 C 0.73410(18) 0.32170(17) -0.06105(12) 0.0222(4) Uani 1 1 d . . . . .
H12 H 0.7325 0.2574 -0.0891 0.027 Uiso 1 1 calc R . . . .
C15 C 0.73725(18) 0.51467(18) 0.02153(13) 0.0236(4) Uani 1 1 d . . . . .
H15 H 0.7380 0.5799 0.0485 0.028 Uiso 1 1 calc R . . . .
C20 C 0.36294(17) 0.94524(18) 0.49980(13) 0.0226(4) Uani 1 1 d . . . . .
H20C H 0.3855 0.8839 0.5524 0.027 Uiso 1 1 calc R . . . .
H20D H 0.3878 1.0044 0.5231 0.027 Uiso 1 1 calc R . . . .
C6 C 0.29605(18) 0.39585(19) 0.49730(14) 0.0269(5) Uani 1 1 d . . . . .
H6 H 0.2690 0.4165 0.5620 0.032 Uiso 1 1 calc R . . . .
C8 C 0.32610(17) 0.26926(18) 0.36538(15) 0.0253(4) Uani 1 1 d . . . . .
H8 H 0.3205 0.2043 0.3419 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4A C1A 1.494(2) . ?
C4A C9A 1.396(2) . ?
C4A C5A 1.399(3) . ?
N3A C2A 1.331(2) . ?
N3A C3A 1.353(2) . ?
C2A N2A 1.352(2) . ?
C2A C10A 1.488(2) . ?
C11A C12A 1.390(3) . ?
C11A C10A 1.390(2) . ?
N2A C1A 1.354(2) . ?
C12A C13A 1.392(3) . ?
C1A N1A 1.328(2) . ?
C6A C7A 1.390(3) . ?
C6A C5A 1.388(2) . ?
N1A C3A 1.357(2) . ?
C15A C14A 1.388(3) . ?
C15A C10A 1.401(2) . ?
C13A C14A 1.384(3) . ?
C9A C8A 1.392(2) . ?
C17A C16A 1.523(3) . ?
C17A C18A 1.527(2) . ?
C16A N4A 1.459(2) . ?
C16A C21A 1.526(2) . ?
C3A N4A 1.335(2) . ?
C21A C20A 1.518(2) . ?
C20A C19A 1.520(3) . ?
C7A C8A 1.382(3) . ?
C18A C19A 1.527(3) . ?
N1 C1 1.328(2) . ?
N1 C3 1.351(2) . ?
N4 C3 1.335(2) . ?
N4 C16 1.461(2) . ?
C4 C1 1.488(2) . ?
C4 C9 1.387(3) . ?
C4 C5 1.399(2) . ?
N3 C3 1.354(2) . ?
N3 C2 1.330(2) . ?
N2 C1 1.346(2) . ?
N2 C2 1.353(2) . ?
C10 C2 1.495(2) . ?
C10 C11 1.389(3) . ?
C10 C15 1.398(2) . ?
C17 C18 1.533(2) . ?
C17 C16 1.527(2) . ?
C9 C8 1.383(2) . ?
C11 C12 1.392(2) . ?
C7 C6 1.384(3) . ?
C7 C8 1.384(3) . ?
C18 C19 1.522(3) . ?
C21 C16 1.516(2) . ?
C21 C20 1.526(2) . ?
C14 C13 1.386(3) . ?
C14 C15 1.390(3) . ?
C5 C6 1.386(2) . ?
C19 C20 1.524(2) . ?
C13 C12 1.379(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9A C4A C1A 121.54(17) . . ?
C9A C4A C5A 118.73(16) . . ?
C5A C4A C1A 119.68(17) . . ?
C2A N3A C3A 114.90(14) . . ?
N3A C2A N2A 125.85(16) . . ?
N3A C2A C10A 115.87(15) . . ?
N2A C2A C10A 118.28(16) . . ?
C10A C11A C12A 120.60(17) . . ?
C2A N2A C1A 114.03(15) . . ?
C11A C12A C13A 120.32(19) . . ?
N2A C1A C4A 118.56(16) . . ?
N1A C1A C4A 115.93(16) . . ?
N1A C1A N2A 125.50(16) . . ?
C5A C6A C7A 119.83(19) . . ?
C1A N1A C3A 115.25(15) . . ?
C14A C15A C10A 120.50(18) . . ?
C14A C13A C12A 119.41(18) . . ?
C8A C9A C4A 120.30(18) . . ?
C16A C17A C18A 111.82(16) . . ?
C17A C16A C21A 111.12(14) . . ?
N4A C16A C17A 109.50(15) . . ?
N4A C16A C21A 111.49(14) . . ?
N3A C3A N1A 124.32(16) . . ?
N4A C3A N3A 118.56(15) . . ?
N4A C3A N1A 117.12(16) . . ?
C3A N4A C16A 124.17(15) . . ?
C20A C21A C16A 109.88(14) . . ?
C21A C20A C19A 110.53(16) . . ?
C8A C7A C6A 119.96(17) . . ?
C17A C18A C19A 110.28(15) . . ?
C6A C5A C4A 120.79(18) . . ?
C7A C8A C9A 120.38(18) . . ?
C13A C14A C15A 120.40(17) . . ?
C20A C19A C18A 110.82(15) . . ?
C11A C10A C2A 120.72(16) . . ?
C11A C10A C15A 118.74(17) . . ?
C15A C10A C2A 120.52(16) . . ?
C1 N1 C3 114.90(14) . . ?
C3 N4 C16 122.20(14) . . ?
C9 C4 C1 120.94(15) . . ?
C9 C4 C5 119.33(16) . . ?
C5 C4 C1 119.71(17) . . ?
C2 N3 C3 114.52(14) . . ?
C1 N2 C2 114.09(15) . . ?
N1 C1 C4 116.00(15) . . ?
N1 C1 N2 125.81(15) . . ?
N2 C1 C4 118.15(16) . . ?
N1 C3 N3 124.81(17) . . ?
N4 C3 N1 117.23(15) . . ?
N4 C3 N3 117.96(15) . . ?
C11 C10 C2 121.33(15) . . ?
C11 C10 C15 119.28(16) . . ?
C15 C10 C2 119.39(17) . . ?
N3 C2 N2 125.84(15) . . ?
N3 C2 C10 117.01(14) . . ?
N2 C2 C10 117.10(16) . . ?
C16 C17 C18 110.11(14) . . ?
C8 C9 C4 120.40(17) . . ?
C10 C11 C12 120.28(16) . . ?
C8 C7 C6 119.98(17) . . ?
C19 C18 C17 112.15(14) . . ?
C16 C21 C20 109.92(14) . . ?
C13 C14 C15 120.10(18) . . ?
C6 C5 C4 119.95(19) . . ?
C18 C19 C20 111.92(16) . . ?
N4 C16 C17 111.62(14) . . ?
N4 C16 C21 110.41(13) . . ?
C21 C16 C17 110.89(15) . . ?
C12 C13 C14 120.09(17) . . ?
C13 C12 C11 120.17(19) . . ?
C14 C15 C10 120.07(19) . . ?
C19 C20 C21 110.76(14) . . ?
C7 C6 C5 120.13(18) . . ?
C9 C8 C7 120.17(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1834205'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_audit_creation_date             2018-03-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C15 H19 Br N3 O'
_chemical_formula_sum            'C15 H19 Br2 N3 O'
_chemical_formula_weight         417.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Br2 C18'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   36.6338(19)
_cell_length_b                   36.6338(19)
_cell_length_c                   6.4707(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7520.5(9)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    4543
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.3530
_cell_measurement_theta_min      4.1470
_shelx_estimated_absorpt_T_max   0.577
_shelx_estimated_absorpt_T_min   0.458
_exptl_absorpt_coefficient_mu    6.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10753
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.196
_diffrn_reflns_theta_min         4.180
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   -9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   38.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega -112.00  -19.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -38.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega    5.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  -99.0000   60.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega   70.00  118.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  178.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   82.00  127.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  178.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega   56.00  100.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   45.00   91.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   84.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   77.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 11 omega   35.00   69.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 12 omega  101.00  165.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
 13 omega   53.00   80.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   95.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 15 omega   30.00   91.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 61

#__ type_ start__ end____ width___ exp.time_
 16 omega   33.00  139.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000   60.0000 106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0396898000
_diffrn_orient_matrix_UB_12      0.0006015000
_diffrn_orient_matrix_UB_13      0.0834712000
_diffrn_orient_matrix_UB_21      -0.0274121000
_diffrn_orient_matrix_UB_22      -0.0356997000
_diffrn_orient_matrix_UB_23      0.1518173000
_diffrn_orient_matrix_UB_31      -0.0052449000
_diffrn_orient_matrix_UB_32      -0.0328685000
_diffrn_orient_matrix_UB_33      -0.1635120000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3239
_reflns_number_total             3449
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.895
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+45.5199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C8(H8), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.56789(2) 0.62671(2) 0.19338(5) 0.02710(11) Uani 1 1 d . . . . .
N1 N 0.61866(8) 0.57371(8) 0.5716(4) 0.0233(5) Uani 1 1 d . . . . .
O1 O 0.64340(7) 0.57946(7) 0.3955(3) 0.0245(5) Uani 1 1 d . . . . .
C1 C 0.60717(10) 0.53590(10) 0.6470(5) 0.0214(6) Uani 1 1 d . . . . .
N3 N 0.66164(9) 0.53670(9) 0.2212(4) 0.0258(6) Uani 1 1 d . . . . .
H3 H 0.6736 0.5568 0.1281 0.031 Uiso 1 1 calc R . . . .
C11 C 0.68135(13) 0.45663(13) -0.0556(5) 0.0352(8) Uani 1 1 d . . . . .
H11A H 0.6906 0.4563 -0.1990 0.042 Uiso 1 1 calc R . . . .
H11B H 0.6539 0.4307 -0.0344 0.042 Uiso 1 1 calc R . . . .
C9 C 0.66383(10) 0.49779(11) 0.1976(5) 0.0251(6) Uani 1 1 d . . . . .
H9 H 0.6354 0.4730 0.2268 0.030 Uiso 1 1 calc R . . . .
C10 C 0.67605(12) 0.49503(12) -0.0257(5) 0.0301(7) Uani 1 1 d . . . . .
H10A H 0.6539 0.4931 -0.1204 0.036 Uiso 1 1 calc R . . . .
H10B H 0.7028 0.5209 -0.0604 0.036 Uiso 1 1 calc R . . . .
C15 C 0.62011(11) 0.61238(10) 0.6401(5) 0.0268(7) Uani 1 1 d . . . . .
H15A H 0.6457 0.6292 0.7215 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.5953 0.6053 0.7253 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.6203 0.6286 0.5193 0.040 Uiso 1 1 calc GR . . . .
N2 N 0.62059(8) 0.51492(8) 0.5276(4) 0.0218(5) Uani 1 1 d . . . . .
C12 C 0.71380(12) 0.45706(13) 0.0960(5) 0.0343(8) Uani 1 1 d . . . . .
H12A H 0.7159 0.4314 0.0767 0.041 Uiso 1 1 calc R . . . .
H12B H 0.7418 0.4819 0.0684 0.041 Uiso 1 1 calc R . . . .
C3 C 0.58110(9) 0.51647(10) 0.8318(4) 0.0208(6) Uani 1 1 d . . . . .
C14 C 0.69561(11) 0.49750(12) 0.3492(5) 0.0293(7) Uani 1 1 d . . . . .
H14A H 0.6862 0.4976 0.4923 0.035 Uiso 1 1 calc R . . . .
H14B H 0.7233 0.5233 0.3295 0.035 Uiso 1 1 calc R . . . .
C13 C 0.70045(12) 0.45883(12) 0.3182(5) 0.0310(7) Uani 1 1 d . . . . .
H13A H 0.6733 0.4330 0.3484 0.037 Uiso 1 1 calc R . . . .
H13B H 0.7219 0.4600 0.4153 0.037 Uiso 1 1 calc R . . . .
C2 C 0.64221(10) 0.54177(10) 0.3778(5) 0.0239(6) Uani 1 1 d . . . . .
C7 C 0.53449(11) 0.45119(10) 1.0072(5) 0.0264(7) Uani 1 1 d . . . . .
H7 H 0.5202 0.4213 1.0138 0.032 Uiso 1 1 calc R . . . .
C8 C 0.56033(10) 0.47259(10) 0.8417(5) 0.0240(6) Uani 1 1 d . . . . .
H8 H 0.5640 0.4572 0.7334 0.029 Uiso 1 1 calc R . . . .
C5 C 0.55039(10) 0.51803(10) 1.1579(5) 0.0246(6) Uani 1 1 d . . . . .
H5 H 0.5468 0.5333 1.2669 0.030 Uiso 1 1 calc R . . . .
C4 C 0.57624(10) 0.53921(10) 0.9916(5) 0.0250(6) Uani 1 1 d . . . . .
H4 H 0.5906 0.5691 0.9865 0.030 Uiso 1 1 calc R . . . .
C6 C 0.52995(10) 0.47470(10) 1.1640(5) 0.0228(6) Uani 1 1 d . . . . .
Br1 Br 0.49512(2) 0.44514(2) 1.39285(5) 0.02638(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.405(3) . ?
N1 C1 1.323(4) . ?
N1 C15 1.460(4) . ?
O1 C2 1.364(4) . ?
C1 N2 1.344(4) . ?
C1 C3 1.473(4) . ?
N3 C9 1.475(4) . ?
N3 C2 1.304(4) . ?
C11 C10 1.525(5) . ?
C11 C12 1.535(5) . ?
C9 C10 1.531(4) . ?
C9 C14 1.526(4) . ?
N2 C2 1.325(4) . ?
C12 C13 1.530(5) . ?
C3 C8 1.394(4) . ?
C3 C4 1.394(4) . ?
C14 C13 1.526(5) . ?
C7 C8 1.384(5) . ?
C7 C6 1.394(4) . ?
C5 C4 1.387(4) . ?
C5 C6 1.376(5) . ?
C6 Br1 1.900(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C15 113.1(2) . . ?
C1 N1 O1 107.4(2) . . ?
C1 N1 C15 137.9(3) . . ?
C2 O1 N1 103.0(2) . . ?
N1 C1 N2 111.8(3) . . ?
N1 C1 C3 126.5(3) . . ?
N2 C1 C3 121.6(3) . . ?
C2 N3 C9 121.0(3) . . ?
C10 C11 C12 111.4(3) . . ?
N3 C9 C10 108.7(3) . . ?
N3 C9 C14 110.5(3) . . ?
C14 C9 C10 110.9(3) . . ?
C11 C10 C9 110.9(3) . . ?
C2 N2 C1 104.5(3) . . ?
C13 C12 C11 109.8(3) . . ?
C8 C3 C1 116.3(3) . . ?
C4 C3 C1 124.0(3) . . ?
C4 C3 C8 119.7(3) . . ?
C9 C14 C13 111.4(3) . . ?
C14 C13 C12 110.5(3) . . ?
N3 C2 O1 117.8(3) . . ?
N3 C2 N2 129.0(3) . . ?
N2 C2 O1 113.2(3) . . ?
C8 C7 C6 118.2(3) . . ?
C7 C8 C3 120.8(3) . . ?
C6 C5 C4 119.6(3) . . ?
C5 C4 C3 119.8(3) . . ?
C7 C6 Br1 117.9(2) . . ?
C5 C6 C7 121.9(3) . . ?
C5 C6 Br1 120.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_17
_database_code_depnum_ccdc_archive 'CCDC 1834204'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_audit_creation_date             2018-03-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 N3 O'
_chemical_formula_sum            'C14 H17 N3 O'
_chemical_formula_weight         243.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N3 O Br C13'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.8808(4)
_cell_length_b                   12.3009(8)
_cell_length_c                   17.6105(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.401(7)
_cell_angle_gamma                90
_cell_volume                     1273.55(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2284
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9550
_cell_measurement_theta_min      3.3160
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.845
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00  -54.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  134.0000  175.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega   66.00   99.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  178.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega   -5.00   93.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00   28.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616    0.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   37.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00   93.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
  7 omega  -24.00   26.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   30.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0059737000
_diffrn_orient_matrix_UB_12      0.0356990000
_diffrn_orient_matrix_UB_13      -0.0314986000
_diffrn_orient_matrix_UB_21      -0.0018248000
_diffrn_orient_matrix_UB_22      0.0452952000
_diffrn_orient_matrix_UB_23      0.0250339000
_diffrn_orient_matrix_UB_31      0.1205114000
_diffrn_orient_matrix_UB_32      0.0024671000
_diffrn_orient_matrix_UB_33      -0.0002775000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2352
_reflns_number_total             2922
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+0.4339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1026
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C10(H10A,H10B), C14(H14A,H14B), C13(H13A,H13B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C8(H8), C7(H7), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 1.16682(18) 0.53065(9) 0.37300(6) 0.0159(3) Uani 1 1 d . . . . .
N3 N 1.35010(19) 0.63940(9) 0.46793(6) 0.0163(3) Uani 1 1 d . . . . .
H3 H 1.4865 0.6200 0.4535 0.020 Uiso 1 1 calc R . . . .
N1 N 0.80323(18) 0.56139(10) 0.40930(6) 0.0165(3) Uani 1 1 d . . . . .
C2 C 1.1700(2) 0.59535(11) 0.43263(7) 0.0145(3) Uani 1 1 d . . . . .
C1 C 0.9384(2) 0.51337(11) 0.36145(7) 0.0149(3) Uani 1 1 d . . . . .
C3 C 0.8510(2) 0.44441(11) 0.29855(7) 0.0153(3) Uani 1 1 d . . . . .
C9 C 1.3323(2) 0.71883(11) 0.52984(7) 0.0152(3) Uani 1 1 d . . . . .
H9 H 1.2168 0.6920 0.5661 0.018 Uiso 1 1 calc R . . . .
C4 C 0.6332(2) 0.46007(12) 0.26652(8) 0.0184(3) Uani 1 1 d . . . . .
H4 H 0.5351 0.5138 0.2864 0.022 Uiso 1 1 calc R . . . .
C8 C 0.9926(2) 0.36420(11) 0.26952(8) 0.0181(3) Uani 1 1 d . . . . .
H8 H 1.1405 0.3538 0.2912 0.022 Uiso 1 1 calc R . . . .
C12 C 1.4737(2) 0.92170(12) 0.60669(8) 0.0198(3) Uani 1 1 d . . . . .
H12A H 1.5885 0.9512 0.5720 0.024 Uiso 1 1 calc R . . . .
H12B H 1.4602 0.9727 0.6499 0.024 Uiso 1 1 calc R . . . .
C7 C 0.9187(3) 0.29943(12) 0.20922(8) 0.0210(3) Uani 1 1 d . . . . .
H7 H 1.0145 0.2440 0.1903 0.025 Uiso 1 1 calc R . . . .
C5 C 0.5620(2) 0.39621(12) 0.20533(8) 0.0210(3) Uani 1 1 d . . . . .
H5 H 0.4153 0.4074 0.1829 0.025 Uiso 1 1 calc R . . . .
C10 C 1.2559(3) 0.82994(12) 0.49988(8) 0.0206(3) Uani 1 1 d . . . . .
H10A H 1.1040 0.8232 0.4748 0.025 Uiso 1 1 calc R . . . .
H10B H 1.3638 0.8557 0.4616 0.025 Uiso 1 1 calc R . . . .
C6 C 0.7026(3) 0.31625(12) 0.17657(8) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.6519 0.2730 0.1348 0.026 Uiso 1 1 calc R . . . .
C14 C 1.5615(2) 0.72707(12) 0.57198(8) 0.0197(3) Uani 1 1 d . . . . .
H14A H 1.6801 0.7485 0.5359 0.024 Uiso 1 1 calc R . . . .
H14B H 1.6033 0.6552 0.5934 0.024 Uiso 1 1 calc R . . . .
C13 C 1.5517(3) 0.81095(12) 0.63619(8) 0.0213(3) Uani 1 1 d . . . . .
H13A H 1.4454 0.7853 0.6751 0.026 Uiso 1 1 calc R . . . .
H13B H 1.7043 0.8181 0.6607 0.026 Uiso 1 1 calc R . . . .
C11 C 1.2448(3) 0.91285(12) 0.56451(8) 0.0226(3) Uani 1 1 d . . . . .
H11A H 1.2017 0.9848 0.5435 0.027 Uiso 1 1 calc R . . . .
H11B H 1.1267 0.8905 0.6004 0.027 Uiso 1 1 calc R . . . .
O1 O 0.96162(15) 0.61835(8) 0.45918(5) 0.0166(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C2 1.3174(17) . ?
N2 C1 1.3702(17) . ?
N3 C2 1.3303(17) . ?
N3 C9 1.4695(17) . ?
N1 C1 1.3129(17) . ?
N1 O1 1.4457(14) . ?
C2 O1 1.3522(16) . ?
C1 C3 1.4776(19) . ?
C3 C4 1.3998(19) . ?
C3 C8 1.3961(19) . ?
C9 C10 1.5288(19) . ?
C9 C14 1.5262(18) . ?
C4 C5 1.390(2) . ?
C8 C7 1.3888(19) . ?
C12 C13 1.525(2) . ?
C12 C11 1.525(2) . ?
C7 C6 1.398(2) . ?
C5 C6 1.388(2) . ?
C10 C11 1.5308(19) . ?
C14 C13 1.5329(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N2 C1 101.94(11) . . ?
C2 N3 C9 123.18(11) . . ?
C1 N1 O1 102.52(10) . . ?
N2 C2 N3 127.90(12) . . ?
N2 C2 O1 114.00(12) . . ?
N3 C2 O1 118.10(12) . . ?
N2 C1 C3 121.49(11) . . ?
N1 C1 N2 116.21(12) . . ?
N1 C1 C3 122.30(12) . . ?
C4 C3 C1 121.42(12) . . ?
C8 C3 C1 118.72(12) . . ?
C8 C3 C4 119.84(13) . . ?
N3 C9 C10 111.35(11) . . ?
N3 C9 C14 109.08(11) . . ?
C14 C9 C10 110.93(12) . . ?
C5 C4 C3 119.34(13) . . ?
C7 C8 C3 120.48(13) . . ?
C13 C12 C11 110.90(12) . . ?
C8 C7 C6 119.61(13) . . ?
C6 C5 C4 120.83(13) . . ?
C9 C10 C11 110.89(11) . . ?
C5 C6 C7 119.89(13) . . ?
C9 C14 C13 110.77(11) . . ?
C12 C13 C14 111.50(11) . . ?
C12 C11 C10 110.91(12) . . ?
C2 O1 N1 105.33(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_18_H2O
_database_code_depnum_ccdc_archive 'CCDC 1834206'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_audit_creation_date             2018-03-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(H4 O2), 2(C14 H18 N4)'
_chemical_formula_sum            'C28 H38 N8 O'
_chemical_formula_weight         502.66
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N4 C14'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   19.3835(2)
_cell_length_b                   18.9731(2)
_cell_length_c                   14.30664(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5261.49(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14147
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.3830
_cell_measurement_theta_min      4.4640
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2160
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17184
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        66.993
_diffrn_reflns_theta_max         66.993
_diffrn_reflns_theta_min         4.493
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00   6.00   0.50    0.83    --  -41.35 112.00  90.00  112
  2  ω    -83.00 -43.00   0.50    0.83    --  -41.35 -21.00  94.00   80
  3  ω     -3.00  22.00   0.50    0.83    --   41.35-112.00  -2.00   50
  4  ω    -23.00  13.00   0.50    0.83    --   41.35 -21.00  94.00   72
  5  ω     29.00  55.00   0.50    0.83    --   41.35-112.00  -2.00   52
  6  ω     24.00 104.00   0.50    3.32    --   93.71 -21.00  94.00  160
  7  ω     81.00 127.00   0.50    3.32    --   93.71 112.00  -1.00   92
  8  ω     67.00  93.00   0.50    3.32    --   93.71-112.00  -2.00   52
  9  ω    113.00 147.00   0.50    3.32    --   93.71 112.00  90.00   68
 10  ω    -60.00 -34.00   0.50    0.83    --  -41.35 112.00  -1.00   52
 11  ω    -10.00  15.00   0.50    0.83    --   41.35 -32.00  30.00   50
 12  ω     69.00  94.00   0.50    0.83    --   41.35  32.00-180.00   50
 13  ω     18.00  48.00   0.50    0.83    --   41.35 -32.00  30.00   60
 14  ω     85.00 155.00   0.50    3.32    --   93.71 117.00 120.00  140
 15  ω     65.00 108.00   0.50    3.32    --   93.71 -96.00-150.00   86
 16  ω     25.00  90.00   0.50    3.32    --   93.71 -96.00 -90.00  130
 17  ω     27.00  52.00   0.50    3.32    --   93.71 -96.00-150.00   50
 18  ω     77.00 102.00   0.50    3.32    --   93.71 -33.00 -90.00   50
 19  ω     69.00 107.00   0.50    3.32    --   93.71 -42.00   0.00   76
 20  ω     39.00  64.00   0.50    0.83    --   41.35  65.00 -90.00   50
 21  ω    -83.00 -57.00   0.50    0.83    --  -41.35 -77.00   0.00   52
 22  ω    -42.00 -16.00   0.50    0.83    --  -41.35 -77.00 -30.00   52
 23  ω    -41.00 -16.00   0.50    0.83    --  -41.35 -77.00   0.00   50
 24  ω     29.00  55.00   0.50    0.83    --   41.35  43.00 -60.00   52
 25  ω     22.00  49.00   0.50    0.83    --   41.35  77.00  30.00   54
 26  ω     17.00  48.00   0.50    0.83    --   41.35  77.00  60.00   62
 27  ω     28.00  70.00   0.50    0.83    --   41.35  43.00   0.00   84
 28  ω     22.00  47.00   0.50    0.83    --   41.35  65.00 -30.00   50
 29  ω     75.00 124.00   0.50    3.32    --   93.71  59.00   0.00   98
 30  ω     80.00 105.00   0.50    3.32    --   93.71  50.00-180.00   50
 31  ω     69.00 141.00   0.50    3.32    --   93.71  77.00 -30.00  144
 32  ω    132.00 157.00   0.50    3.32    --   93.71  50.00-180.00   50
 33  ω     72.00 133.00   0.50    3.32    --   93.71  68.00   0.00  122
 34  ω     72.00 112.00   0.50    3.32    --   93.71  68.00 -30.00   80
 35  ω     68.00  94.00   0.50    3.32    --   93.71  77.00  30.00   52
 36  ω    125.00 157.00   0.50    3.32    --   93.71  77.00   0.00   64
 37  ω     78.00 104.00   0.50    3.32    --   93.71  59.00  30.00   52
 38  ω    120.00 146.00   0.50    3.32    --   93.71  68.00  30.00   52
 39  ω     74.00 105.00   0.50    3.32    --   93.71 -96.00 -60.00   62
 40  ω     72.00 100.00   0.50    3.32    --   93.71  68.00  30.00   56
 41  ω     68.00  93.00   0.50    3.32    --   93.71  77.00   0.00   50
 42  ω    101.00 126.00   0.50    3.32    --   93.71  77.00 -60.00   50
 43  ω     69.00  98.00   0.50    3.32    --   93.71  77.00 -60.00   58
 44  ω     88.00 114.00   0.50    3.32    --   93.71 112.00  90.00   52
 45  ω    -73.00 -34.00   0.50    0.83    --  -41.35 -32.00-180.00   78
 46  ω      4.00  35.00   0.50    0.83    --   41.35 -43.00 150.00   62
 47  ω     93.00 119.00   0.50    3.32    --   93.71-145.00 120.00   52
 48  ω     73.00  99.00   0.50    3.32    --   93.71 -42.00  30.00   52
 49  ω     94.00 131.00   0.50    3.32    --   93.71-145.00-150.00   74
 50  ω     30.00  55.00   0.50    3.32    --   93.71-145.00-150.00   50
 51  ω     38.00  63.00   0.50    3.32    --   93.71 -42.00  30.00   50
 52  ω     38.00  68.00   0.50    3.32    --   93.71-145.00 120.00   60
 53  ω     49.00  97.00   0.50    3.32    --   93.71 -68.00 -60.00   96
 54  ω     25.00 108.00   0.50    3.32    --   93.71 -96.00 120.00  166
 55  ω     52.00  78.00   0.50    0.83    --   41.35-112.00  -2.00   52
 56  ω    -56.00 -16.00   0.50    0.83    --  -41.35 -77.00-120.00   80
 57  ω    -58.00 -33.00   0.50    0.83    --  -41.35 -32.00  30.00   50
 58  ω   -107.00 -78.00   0.50    0.83    --  -41.35 -32.00  30.00   58
 59  ω     39.00  65.00   0.50    0.83    --   41.35  32.00  90.00   52
 60  ω     22.00  48.00   0.50    0.83    --   41.35 -32.00 -60.00   52
 61  ω     75.00 107.00   0.50    0.83    --   41.35  32.00  90.00   64
 62  ω     42.00  68.00   0.50    0.83    --   41.35 -89.00-150.00   52
 63  ω    -23.00   4.00   0.50    0.83    --   41.35 -89.00-150.00   54
 64  ω    127.00 153.00   0.50    3.32    --   93.71  17.00-180.00   52
 65  ω     31.00 103.00   0.50    3.32    --   93.71 -59.00 120.00  144
 66  ω     77.00 117.00   0.50    3.32    --   93.71-117.00-150.00   80
 67  ω     68.00 114.00   0.50    3.32    --   93.71 145.00 150.00   92
 68  ω     47.00  73.00   0.50    3.32    --   93.71-117.00-150.00   52
 69  ω     65.00 100.00   0.50    3.32    --   93.71-117.00 -30.00   70
 70  ω     95.00 121.00   0.50    3.32    --   93.71  17.00-180.00   52
 71  ω     84.00 113.00   0.50    3.32    --   93.71 -68.00  60.00   58
 72  ω     34.00  60.00   0.50    3.32    --   93.71 -68.00  60.00   52
 73  ω     52.00  93.00   0.50    3.32    --   93.71 -42.00 -30.00   82
 74  ω     71.00  97.00   0.50    3.32    --   93.71 -17.00-120.00   52
 75  ω     26.00  52.00   0.50    3.32    --   93.71 -17.00-120.00   52
 76  ω     38.00 107.00   0.50    3.32    --   93.71 -17.00   0.00  138
 77  ω     24.00  56.00   0.50    3.32    --   93.71 -96.00  30.00   64
 78  ω     64.00 103.00   0.50    3.32    --   93.71 -96.00  30.00   78
 79  ω    108.00 134.00   0.50    3.32    --   93.71  33.00  60.00   52
 80  ω     47.00 100.00   0.50    3.32    --   93.71 -77.00  30.00  106
 81  ω     85.00 111.00   0.50    3.32    --   93.71  33.00-120.00   52
 82  ω     90.00 157.00   0.50    3.32    --   93.71  33.00-150.00  134
 83  ω   -100.00 -74.00   0.50    0.83    --  -41.35 -21.00  95.00   52
 84  ω     54.00  80.00   0.50    0.83    --   41.35  32.00-120.00   52
 85  ω     36.00  74.00   0.50    0.83    --   41.35-138.00-150.00   76
 86  ω     31.00  71.00   0.50    3.32    --   93.71 -68.00-150.00   80
 87  ω     97.00 123.00   0.50    3.32    --   93.71  33.00  30.00   52
 88  ω     85.00 131.00   0.50    3.32    --   93.71  33.00 -90.00   92
 89  ω     72.00  97.00   0.50    3.32    --   93.71  77.00 -90.00   50
 90  ω     68.00  98.00   0.50    3.32    --   93.71 -68.00  90.00   60
 91  ω    104.00 130.00   0.50    3.32    --   93.71  77.00 -90.00   52
 92  ω     86.00 112.00   0.50    3.32    --   93.71 -68.00-150.00   52
 93  ω    105.00 135.00   0.50    3.32    --   93.71 117.00  30.00   60
 94  ω    107.00 156.00   0.50    3.32    --   93.71  96.00  60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0038637000
_diffrn_orient_matrix_UB_12      -0.0780521000
_diffrn_orient_matrix_UB_13      -0.0292901000
_diffrn_orient_matrix_UB_21      -0.0793771500
_diffrn_orient_matrix_UB_22      0.0039861500
_diffrn_orient_matrix_UB_23      0.0007556000
_diffrn_orient_matrix_UB_31      0.0005218000
_diffrn_orient_matrix_UB_32      0.0220927000
_diffrn_orient_matrix_UB_33      -0.1036016000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.885
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                2201
_reflns_number_total             2222
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.18(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+3.0408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0630
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5)
3.a Riding coordinates:
 C6(H3)
3.b Free rotating group:
 O1(H1A,H1B)
3.c Ternary CH refined with riding coordinates:
 C9(H9)
3.d Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C12(H12A,H12B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
3.e Aromatic/amide H refined with riding coordinates:
 N4(H4), C4(H4A), C5(H5), C8(H8), C7(H7), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5000 0.5000 0.59203(12) 0.0156(3) Uani 1 2 d S T P . .
H1A H 0.4788 0.4698 0.6251 0.023 Uiso 0.5 1 d G . . A -1
H1B H 0.5294 0.5181 0.6290 0.023 Uiso 0.5 1 d G . . B -1
N1 N 0.33609(7) 0.55636(7) 0.53138(10) 0.0183(3) Uani 1 1 d . . . . .
N4 N 0.40006(7) 0.58700(7) 0.51785(11) 0.0172(3) Uani 1 1 d . . . . .
H4 H 0.4395 0.5690 0.5366 0.021 Uiso 1 1 calc R . . . .
N2 N 0.32617(7) 0.66007(7) 0.45353(10) 0.0166(3) Uani 1 1 d . . . . .
N3 N 0.44558(7) 0.69200(7) 0.44869(10) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.29445(8) 0.60172(8) 0.49082(12) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.39300(8) 0.64828(8) 0.47188(12) 0.0160(3) Uani 1 1 d . . . . .
C4 C 0.19371(9) 0.52423(9) 0.45987(13) 0.0215(4) Uani 1 1 d . . . . .
H4A H 0.2246 0.4870 0.4451 0.026 Uiso 1 1 calc R . . . .
C9 C 0.51740(8) 0.67503(8) 0.47213(12) 0.0171(3) Uani 1 1 d . . . . .
H9 H 0.5180 0.6554 0.5370 0.021 Uiso 1 1 calc R . . . .
C14 C 0.56028(8) 0.74262(8) 0.47232(13) 0.0199(4) Uani 1 1 d . . . . .
H14A H 0.5401 0.7765 0.5173 0.024 Uiso 1 1 calc R . . . .
H14B H 0.5588 0.7643 0.4094 0.024 Uiso 1 1 calc R . . . .
C3 C 0.21925(9) 0.59002(8) 0.48589(12) 0.0172(3) Uani 1 1 d . . . . .
C5 C 0.12296(10) 0.51313(10) 0.45553(14) 0.0268(4) Uani 1 1 d . . . . .
H5 H 0.1055 0.4684 0.4373 0.032 Uiso 1 1 calc R . . . .
C12 C 0.66786(9) 0.67135(10) 0.43672(14) 0.0239(4) Uani 1 1 d . . . . .
H12A H 0.6715 0.6893 0.3719 0.029 Uiso 1 1 calc R . . . .
H12B H 0.7149 0.6603 0.4591 0.029 Uiso 1 1 calc R . . . .
C10 C 0.54974(9) 0.62018(9) 0.40715(13) 0.0204(4) Uani 1 1 d . . . . .
H10A H 0.5497 0.6381 0.3422 0.025 Uiso 1 1 calc R . . . .
H10B H 0.5222 0.5763 0.4089 0.025 Uiso 1 1 calc R . . . .
C11 C 0.62391(9) 0.60456(9) 0.43775(14) 0.0233(4) Uani 1 1 d . . . . .
H11A H 0.6236 0.5844 0.5016 0.028 Uiso 1 1 calc R . . . .
H11B H 0.6444 0.5692 0.3951 0.028 Uiso 1 1 calc R . . . .
C8 C 0.17338(9) 0.64446(9) 0.50693(14) 0.0218(4) Uani 1 1 d . . . . .
H8 H 0.1905 0.6897 0.5234 0.026 Uiso 1 1 calc R . . . .
C13 C 0.63575(9) 0.72789(9) 0.49929(13) 0.0221(4) Uani 1 1 d . . . . .
H13A H 0.6628 0.7720 0.4938 0.027 Uiso 1 1 calc R . . . .
H13B H 0.6377 0.7122 0.5652 0.027 Uiso 1 1 calc R . . . .
C7 C 0.10298(9) 0.63257(10) 0.50389(15) 0.0284(4) Uani 1 1 d . . . . .
H7 H 0.0719 0.6694 0.5198 0.034 Uiso 1 1 calc R . . . .
C6 C 0.07759(9) 0.56726(11) 0.47776(15) 0.0302(4) Uani 1 1 d . . . . .
H6 H 0.0292 0.5595 0.4751 0.036 Uiso 1 1 calc R . . . .
H3 H 0.4359 0.7221 0.4028 0.036 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1A 0.8497 . ?
O1 H1B 0.8505 . ?
N1 N4 1.3832(19) . ?
N1 C1 1.315(2) . ?
N4 H4 0.8800 . ?
N4 C2 1.343(2) . ?
N2 C1 1.374(2) . ?
N2 C2 1.340(2) . ?
N3 C2 1.355(2) . ?
N3 C9 1.468(2) . ?
N3 H3 0.8902 . ?
C1 C3 1.476(2) . ?
C4 H4A 0.9500 . ?
C4 C3 1.394(2) . ?
C4 C5 1.389(3) . ?
C9 H9 1.0000 . ?
C9 C14 1.528(2) . ?
C9 C10 1.530(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.538(2) . ?
C3 C8 1.396(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.527(2) . ?
C12 C13 1.530(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.532(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 H8 0.9500 . ?
C8 C7 1.384(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C7 H7 0.9500 . ?
C7 C6 1.385(3) . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A O1 H1B 104.5 . . ?
C1 N1 N4 102.32(13) . . ?
N1 N4 H4 125.0 . . ?
C2 N4 N1 109.94(13) . . ?
C2 N4 H4 125.0 . . ?
C2 N2 C1 102.81(13) . . ?
C2 N3 C9 121.54(13) . . ?
C2 N3 H3 114.5 . . ?
C9 N3 H3 120.6 . . ?
N1 C1 N2 115.10(14) . . ?
N1 C1 C3 121.91(14) . . ?
N2 C1 C3 122.99(14) . . ?
N4 C2 N3 124.97(14) . . ?
N2 C2 N4 109.82(14) . . ?
N2 C2 N3 125.21(14) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C5 C4 C3 119.91(16) . . ?
N3 C9 H9 107.8 . . ?
N3 C9 C14 109.41(12) . . ?
N3 C9 C10 113.52(14) . . ?
C14 C9 H9 107.8 . . ?
C14 C9 C10 110.43(14) . . ?
C10 C9 H9 107.8 . . ?
C9 C14 H14A 109.3 . . ?
C9 C14 H14B 109.3 . . ?
C9 C14 C13 111.42(13) . . ?
H14A C14 H14B 108.0 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C4 C3 C1 119.90(14) . . ?
C4 C3 C8 119.61(16) . . ?
C8 C3 C1 120.49(15) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.20(17) . . ?
C6 C5 H5 119.9 . . ?
H12A C12 H12B 108.1 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C11 C12 C13 110.44(14) . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C9 C10 C11 110.03(14) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C12 C11 C10 111.12(14) . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.05(17) . . ?
C7 C8 H8 120.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 C14 111.57(15) . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C8 C7 H7 119.8 . . ?
C8 C7 C6 120.32(16) . . ?
C6 C7 H7 119.8 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.89(16) . . ?
C7 C6 H6 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.067
_oxdiff_exptl_absorpt_empirical_full_min 0.798
####################################################################### 
# 
# 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_20
_database_code_depnum_ccdc_archive 'CCDC 1834208'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_audit_creation_date             2018-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 N2 O2'
_chemical_formula_sum            'C14 H18 N2 O2'
_chemical_formula_weight         246.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   20.2808(13)
_cell_length_b                   5.2993(4)
_cell_length_c                   24.3454(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.356(6)
_cell_angle_gamma                90
_cell_volume                     2588.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1116
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4740
_cell_measurement_theta_min      3.6680
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5755
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.825
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00  -37.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  178.0000  -60.0000 62

#__ type_ start__ end____ width___ exp.time_
  2 omega  -40.00   20.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   60.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00   59.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616    0.0000   60.0000 104
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0023793000
_diffrn_orient_matrix_UB_12      0.1311763000
_diffrn_orient_matrix_UB_13      -0.0050585000
_diffrn_orient_matrix_UB_21      0.0350469000
_diffrn_orient_matrix_UB_22      -0.0059805000
_diffrn_orient_matrix_UB_23      0.0079145000
_diffrn_orient_matrix_UB_31      0.0040765000
_diffrn_orient_matrix_UB_32      -0.0255159000
_diffrn_orient_matrix_UB_33      -0.0279162000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2256
_reflns_number_total             2969
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+1.0710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1245
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4), C5(H5), C6(H6), C8(H8), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69765(5) 0.4191(2) 0.58950(4) 0.0199(3) Uani 1 1 d . . . . .
O2 O 0.78858(6) 0.9058(3) 0.70744(4) 0.0214(3) Uani 1 1 d . . . . .
N1 N 0.72326(6) 0.5694(3) 0.67770(5) 0.0157(3) Uani 1 1 d . . . . .
H1 H 0.7165 0.5462 0.7122 0.019 Uiso 1 1 calc R . . . .
N2 N 0.78266(6) 0.7927(3) 0.61746(5) 0.0158(3) Uani 1 1 d . . . . .
H2 H 0.7667 0.6852 0.5913 0.019 Uiso 1 1 calc R . . . .
C9 C 0.82609(7) 0.9978(3) 0.60431(5) 0.0147(3) Uani 1 1 d . . . . .
H9 H 0.8125 1.1550 0.6224 0.018 Uiso 1 1 calc R . . . .
C2 C 0.76685(7) 0.7662(3) 0.66843(6) 0.0151(3) Uani 1 1 d . . . . .
C1 C 0.69015(7) 0.4097(3) 0.63867(6) 0.0152(3) Uani 1 1 d . . . . .
C3 C 0.64423(7) 0.2181(3) 0.65793(6) 0.0153(3) Uani 1 1 d . . . . .
C4 C 0.61250(8) 0.0540(3) 0.61774(6) 0.0179(4) Uani 1 1 d . . . . .
H4 H 0.6199 0.0711 0.5803 0.022 Uiso 1 1 calc R . . . .
C10 C 0.89954(8) 0.9471(4) 0.62609(6) 0.0191(4) Uani 1 1 d . . . . .
H10A H 0.9053 0.9252 0.6669 0.023 Uiso 1 1 calc R . . . .
H10B H 0.9138 0.7893 0.6095 0.023 Uiso 1 1 calc R . . . .
C5 C 0.57043(8) -0.1334(4) 0.63172(7) 0.0213(4) Uani 1 1 d . . . . .
H5 H 0.5493 -0.2444 0.6040 0.026 Uiso 1 1 calc R . . . .
C14 C 0.81583(8) 1.0410(4) 0.54162(6) 0.0195(4) Uani 1 1 d . . . . .
H14A H 0.7686 1.0837 0.5289 0.023 Uiso 1 1 calc R . . . .
H14B H 0.8263 0.8839 0.5226 0.023 Uiso 1 1 calc R . . . .
C11 C 0.94270(8) 1.1655(4) 0.61153(7) 0.0218(4) Uani 1 1 d . . . . .
H11A H 0.9901 1.1280 0.6250 0.026 Uiso 1 1 calc R . . . .
H11B H 0.9305 1.3208 0.6303 0.026 Uiso 1 1 calc R . . . .
C6 C 0.55903(8) -0.1592(4) 0.68636(7) 0.0220(4) Uani 1 1 d . . . . .
H6 H 0.5304 -0.2883 0.6961 0.026 Uiso 1 1 calc R . . . .
C8 C 0.63242(8) 0.1928(4) 0.71284(6) 0.0215(4) Uani 1 1 d . . . . .
H8 H 0.6534 0.3034 0.7407 0.026 Uiso 1 1 calc R . . . .
C13 C 0.86029(9) 1.2543(4) 0.52610(6) 0.0238(4) Uani 1 1 d . . . . .
H13A H 0.8552 1.2693 0.4852 0.029 Uiso 1 1 calc R . . . .
H13B H 0.8458 1.4155 0.5411 0.029 Uiso 1 1 calc R . . . .
C7 C 0.58971(8) 0.0046(4) 0.72643(6) 0.0249(4) Uani 1 1 d . . . . .
H7 H 0.5815 -0.0116 0.7637 0.030 Uiso 1 1 calc R . . . .
C12 C 0.93343(9) 1.2088(4) 0.54868(7) 0.0261(4) Uani 1 1 d . . . . .
H12A H 0.9601 1.3565 0.5403 0.031 Uiso 1 1 calc R . . . .
H12B H 0.9497 1.0595 0.5302 0.031 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2294(17) . ?
O2 C2 1.2337(19) . ?
N1 C2 1.406(2) . ?
N1 C1 1.373(2) . ?
N2 C9 1.463(2) . ?
N2 C2 1.3332(18) . ?
C9 C10 1.531(2) . ?
C9 C14 1.5274(19) . ?
C1 C3 1.498(2) . ?
C3 C4 1.394(2) . ?
C3 C8 1.398(2) . ?
C4 C5 1.384(2) . ?
C10 C11 1.524(2) . ?
C5 C6 1.390(2) . ?
C14 C13 1.527(2) . ?
C11 C12 1.532(2) . ?
C6 C7 1.384(2) . ?
C8 C7 1.392(2) . ?
C13 C12 1.524(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 126.99(13) . . ?
C2 N2 C9 121.05(13) . . ?
N2 C9 C10 112.37(14) . . ?
N2 C9 C14 109.34(12) . . ?
C14 C9 C10 110.91(12) . . ?
O2 C2 N1 118.92(13) . . ?
O2 C2 N2 123.09(15) . . ?
N2 C2 N1 117.99(14) . . ?
O1 C1 N1 122.13(15) . . ?
O1 C1 C3 120.16(14) . . ?
N1 C1 C3 117.71(13) . . ?
C4 C3 C1 116.58(13) . . ?
C4 C3 C8 119.02(15) . . ?
C8 C3 C1 124.39(15) . . ?
C5 C4 C3 120.88(14) . . ?
C11 C10 C9 110.45(14) . . ?
C4 C5 C6 120.03(15) . . ?
C9 C14 C13 111.02(13) . . ?
C10 C11 C12 110.78(14) . . ?
C7 C6 C5 119.51(17) . . ?
C7 C8 C3 119.68(15) . . ?
C12 C13 C14 111.86(15) . . ?
C6 C7 C8 120.88(15) . . ?
C13 C12 C11 110.84(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
