# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ag
_database_code_depnum_ccdc_archive 'CCDC 2006514'
loop_
_audit_author_name
_audit_author_address
'Debasish Haldar'
;IISER Kolkata
India
;
_audit_update_record             
;
2020-10-15 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2020-10-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            Boc-Phe-Aib-OMe
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H28 N2 O5'
_chemical_formula_sum            'C19 H28 N2 O5'
_chemical_formula_weight         364.43
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   8.279(17)
_cell_length_b                   11.90(3)
_cell_length_c                   20.37(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2007(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      18.845
_cell_measurement_theta_min      2.659
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2007/4 (Bruker,2007/4) was used for absorption correction.
wR2(int) was 0.1691 before and 0.0765 after correction.
The Ratio of minimum to maximum transmission is 0.4688.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2736
_exptl_crystal_size_mid          0.2365
_exptl_crystal_size_min          0.1978
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1756
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17227
_diffrn_reflns_theta_full        28.038
_diffrn_reflns_theta_max         28.008
_diffrn_reflns_theta_min         1.98
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1519
_reflns_number_total             2144
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0809P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1460
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C13(H13), C17(H17), C16(H16), C15(H15), C14(H14)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C3(H3A,H3B,H3C), C10(H10A,H10B,
 H10C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.5338(5) 0.1781(3) 0.82827(17) 0.0523(10) Uani 1 d . . .
O2 O 0.5236(5) -0.0082(3) 0.81019(17) 0.0553(11) Uani 1 d . . .
O4 O -0.1540(5) 0.4501(3) 0.80287(19) 0.0655(12) Uani 1 d . . .
O5 O -0.0026(5) 0.4176(3) 0.71483(18) 0.0653(11) Uani 1 d . . .
O3 O 0.1340(5) 0.2160(3) 0.7943(2) 0.0680(12) Uani 1 d . . .
N1 N 0.4107(5) 0.1135(3) 0.7410(2) 0.0455(12) Uani 1 d . . .
H1 H 0.3877 0.0607 0.7139 0.055 Uiso 1 calc . . R
N2 N 0.2558(5) 0.3811(4) 0.7837(2) 0.0487(12) Uani 1 d . . .
H2 H 0.3436 0.4144 0.7723 0.058 Uiso 1 calc . . R
C6 C 0.3625(7) 0.2269(4) 0.7249(2) 0.0432(13) Uani 1 d . . .
H6 H 0.4582 0.2752 0.7253 0.052 Uiso 1 calc . . R
C7 C 0.2411(8) 0.2722(5) 0.7722(3) 0.0486(14) Uani 1 d . . .
C5 C 0.4883(7) 0.0868(5) 0.7954(3) 0.0481(13) Uani 1 d . . .
C9 C -0.0224(8) 0.4350(4) 0.7783(3) 0.0540(15) Uani 1 d . . .
C12 C 0.4038(7) 0.1943(4) 0.6038(2) 0.0471(15) Uani 1 d . . .
C11 C 0.2915(7) 0.2282(4) 0.6574(2) 0.0499(16) Uani 1 d . . .
H11A H 0.1992 0.1782 0.6569 0.060 Uiso 1 calc . . R
H11B H 0.2522 0.3034 0.6481 0.060 Uiso 1 calc . . R
C13 C 0.5250(9) 0.2658(5) 0.5855(3) 0.0631(17) Uani 1 d . . .
H13 H 0.5357 0.3347 0.6064 0.076 Uiso 1 calc . . R
C8 C 0.1282(7) 0.4468(4) 0.8153(3) 0.0529(15) Uani 1 d . . .
C4 C 0.5998(9) 0.1708(5) 0.8942(3) 0.0602(17) Uani 1 d . . .
C17 C 0.3918(9) 0.0939(5) 0.5727(3) 0.0637(17) Uani 1 d . . .
H17 H 0.3118 0.0435 0.5851 0.076 Uiso 1 calc . . R
C19 C 0.1796(7) 0.5703(4) 0.8101(3) 0.075(2) Uani 1 d . . .
H19A H 0.2872 0.5784 0.8269 0.113 Uiso 1 calc . . GR
H19B H 0.1067 0.6161 0.8353 0.113 Uiso 1 calc . . GR
H19C H 0.1772 0.5937 0.7650 0.113 Uiso 1 calc . . GR
C16 C 0.4967(11) 0.0663(5) 0.5231(3) 0.0769(19) Uani 1 d . . .
H16 H 0.4859 -0.0019 0.5014 0.092 Uiso 1 calc . . R
C18 C 0.1096(8) 0.4138(5) 0.8862(3) 0.0739(19) Uani 1 d . . .
H18A H 0.0775 0.3365 0.8890 0.111 Uiso 1 calc . . GR
H18B H 0.0288 0.4603 0.9064 0.111 Uiso 1 calc . . GR
H18C H 0.2107 0.4235 0.9084 0.111 Uiso 1 calc . . GR
C15 C 0.6140(11) 0.1367(6) 0.5058(3) 0.084(2) Uani 1 d . . .
H15 H 0.6853 0.1172 0.4723 0.101 Uiso 1 calc . . R
C14 C 0.6305(10) 0.2365(6) 0.5367(3) 0.084(2) Uani 1 d . . .
H14 H 0.7133 0.2851 0.5248 0.101 Uiso 1 calc . . R
C3 C 0.6135(10) 0.2915(5) 0.9130(3) 0.091(2) Uani 1 d . . .
H3A H 0.6847 0.3292 0.8829 0.136 Uiso 1 calc . . GR
H3B H 0.6558 0.2968 0.9567 0.136 Uiso 1 calc . . GR
H3C H 0.5087 0.3262 0.9114 0.136 Uiso 1 calc . . GR
C10 C -0.1419(8) 0.4144(6) 0.6745(3) 0.094(2) Uani 1 d . . .
H10A H -0.1117 0.3914 0.6310 0.141 Uiso 1 calc . . GR
H10B H -0.1903 0.4878 0.6727 0.141 Uiso 1 calc . . GR
H10C H -0.2180 0.3619 0.6925 0.141 Uiso 1 calc . . GR
C1 C 0.7649(10) 0.1191(6) 0.8912(4) 0.115(3) Uani 1 d . . .
H1A H 0.7562 0.0417 0.8786 0.172 Uiso 1 calc . . GR
H1B H 0.8148 0.1238 0.9336 0.172 Uiso 1 calc . . GR
H1C H 0.8294 0.1587 0.8595 0.172 Uiso 1 calc . . GR
C2 C 0.4869(12) 0.1097(6) 0.9373(3) 0.114(3) Uani 1 d . . .
H2A H 0.3832 0.1460 0.9362 0.171 Uiso 1 calc . . GR
H2B H 0.5273 0.1097 0.9814 0.171 Uiso 1 calc . . GR
H2C H 0.4765 0.0337 0.9223 0.171 Uiso 1 calc . . GR


_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 C5 1.334(6) . ?
O1 C4 1.453(7) . ?
O2 C5 1.204(6) . ?
O4 C9 1.211(7) . ?
O5 C9 1.320(7) . ?
O5 C10 1.418(7) . ?
O3 C7 1.198(7) . ?
N1 H1 0.8600 . ?
N1 C6 1.444(7) . ?
N1 C5 1.320(6) . ?
N2 H2 0.8600 . ?
N2 C7 1.324(7) . ?
N2 C8 1.461(7) . ?
C6 H6 0.9800 . ?
C6 C7 1.491(8) . ?
C6 C11 1.497(7) . ?
C9 C8 1.466(8) . ?
C12 C11 1.488(7) . ?
C12 C13 1.367(8) . ?
C12 C17 1.358(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.366(9) . ?
C8 C19 1.535(8) . ?
C8 C18 1.503(8) . ?
C4 C3 1.494(8) . ?
C4 C1 1.497(10) . ?
C4 C2 1.472(9) . ?
C17 H17 0.9300 . ?
C17 C16 1.370(8) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C15 1.330(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C14 1.354(9) . ?
C14 H14 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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
C5 O1 C4 121.7(4) . . ?
C9 O5 C10 118.3(5) . . ?
C6 N1 H1 118.4 . . ?
C5 N1 H1 118.4 . . ?
C5 N1 C6 123.2(4) . . ?
C7 N2 H2 118.8 . . ?
C7 N2 C8 122.3(5) . . ?
C8 N2 H2 118.8 . . ?
N1 C6 H6 108.9 . . ?
N1 C6 C7 112.1(4) . . ?
N1 C6 C11 108.9(4) . . ?
C7 C6 H6 108.9 . . ?
C7 C6 C11 109.0(5) . . ?
C11 C6 H6 108.9 . . ?
O3 C7 N2 123.3(6) . . ?
O3 C7 C6 122.5(5) . . ?
N2 C7 C6 114.0(6) . . ?
O2 C5 O1 124.8(6) . . ?
O2 C5 N1 123.4(5) . . ?
N1 C5 O1 111.5(5) . . ?
O4 C9 O5 122.5(6) . . ?
O4 C9 C8 122.6(6) . . ?
O5 C9 C8 114.6(5) . . ?
C13 C12 C11 119.1(5) . . ?
C17 C12 C11 122.3(6) . . ?
C17 C12 C13 118.5(6) . . ?
C6 C11 H11A 108.5 . . ?
C6 C11 H11B 108.5 . . ?
C12 C11 C6 115.2(5) . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(6) . . ?
C14 C13 H13 119.8 . . ?
N2 C8 C9 109.6(5) . . ?
N2 C8 C19 106.4(5) . . ?
N2 C8 C18 110.9(5) . . ?
C9 C8 C19 107.3(5) . . ?
C9 C8 C18 112.5(5) . . ?
C18 C8 C19 109.9(5) . . ?
O1 C4 C3 102.3(5) . . ?
O1 C4 C1 109.3(5) . . ?
O1 C4 C2 109.8(6) . . ?
C3 C4 C1 109.5(6) . . ?
C2 C4 C3 111.8(6) . . ?
C2 C4 C1 113.6(6) . . ?
C12 C17 H17 119.7 . . ?
C12 C17 C16 120.6(6) . . ?
C16 C17 H17 119.7 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.2(6) . . ?
C15 C16 H16 119.9 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C14 120.5(7) . . ?
C14 C15 H15 119.8 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(7) . . ?
C15 C14 H14 120.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 N1 C6 -8.1(7) . . . . ?
N1 C6 C7 N2 145.3(5) . . . . ?
N2 C8 C9 O5 -29.8(6) . . . . ?
C6 C7 N2 C8 164.8(5) . . . . ?
C7 N2 C8 C9 -55.8(6) . . . . ?
C5 N1 C6 C7 -64.5(7) . . . . ?
C8 C9 O5 C10 -174.9(5) . . . . ?
C4 O1 C5 N1 170.8(5) . . . . ?
C1 C4 O1 C5 70.5(7) . . . . ?

_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_npgphe
_database_code_depnum_ccdc_archive 'CCDC 2006562'
loop_
_audit_author_name
_audit_author_address
'Debasish Haldar'
;IISER Kolkata
India
;
_audit_update_record             
;
2020-10-15 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2020-10-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            N-PhenylGly-Phe-OMe
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H20 N2 O3'
_chemical_formula_sum            'C18 H20 N2 O3'
_chemical_formula_weight         312.36
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   10.9817(6)
_cell_length_b                   5.3645(3)
_cell_length_c                   14.6541(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.547(6)
_cell_angle_gamma                90.00
_cell_volume                     813.54(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3359
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      66.0440
_cell_measurement_theta_min      3.1950
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.2581
_exptl_crystal_size_mid          0.2265
_exptl_crystal_size_min          0.1986
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5989
_diffrn_reflns_theta_full        65.98
_diffrn_reflns_theta_max         65.98
_diffrn_reflns_theta_min         4.27
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       24.0811   57.0000 -150.0000 114

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       24.0811   57.0000    0.0000 114

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       24.0811   57.0000  -90.0000 114

#__ type_ start__ end____ width___ exp.time_
  4 omega  -14.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       24.0811   57.0000  -30.0000 114

#__ type_ start__ end____ width___ exp.time_
  5 omega   -4.00  108.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406  -94.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
  6 omega  100.00  151.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406  111.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
  7 omega  100.00  151.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406  111.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega  102.00  152.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406  104.0000  146.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega  100.00  151.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406  111.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
 10 omega  -20.00  154.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406   15.0000  -90.0000 174

#__ type_ start__ end____ width___ exp.time_
 11 omega   21.00  178.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -21.0000   30.0000 157

#__ type_ start__ end____ width___ exp.time_
 12 omega   69.00  178.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000   30.0000 109

#__ type_ start__ end____ width___ exp.time_
 13 omega   21.00  178.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -21.0000   30.0000 157

#__ type_ start__ end____ width___ exp.time_
 14 omega   29.00  145.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000 -180.0000 116

#__ type_ start__ end____ width___ exp.time_
 15 omega  101.00  178.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  146.0000 77

#__ type_ start__ end____ width___ exp.time_
 16 omega   69.00  178.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000  -90.0000 109

#__ type_ start__ end____ width___ exp.time_
 17 omega   58.00  178.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000  -30.0000 120

#__ type_ start__ end____ width___ exp.time_
 18 omega   21.00  113.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
 19 omega   21.00  113.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000 -150.0000 92

#__ type_ start__ end____ width___ exp.time_
 20 omega   21.00  113.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000    0.0000 92

#__ type_ start__ end____ width___ exp.time_
 21 omega   29.00  145.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000    0.0000 116

#__ type_ start__ end____ width___ exp.time_
 22 omega  -63.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       24.0811  -19.0000 -150.0000 171

#__ type_ start__ end____ width___ exp.time_
 23 omega   55.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       24.0811 -178.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
 24 omega   57.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       24.0811  178.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
 25 omega  -14.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       24.0811   57.0000   90.0000 114

#__ type_ start__ end____ width___ exp.time_
 26 omega   23.00  151.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406   77.0000  -30.0000 128

#__ type_ start__ end____ width___ exp.time_
 27 omega  100.00  151.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406  111.0000    0.0000 51

#__ type_ start__ end____ width___ exp.time_
 28 omega   29.00  143.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406   61.0000   60.0000 114

#__ type_ start__ end____ width___ exp.time_
 29 omega  100.00  151.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406  111.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
 30 omega   23.00   48.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406   77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   29.00  143.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0406   61.0000  120.0000 114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1441692000
_diffrn_orient_matrix_UB_12      -0.0035863000
_diffrn_orient_matrix_UB_13      -0.0101447000
_diffrn_orient_matrix_UB_21      0.0349447000
_diffrn_orient_matrix_UB_22      0.0775546000
_diffrn_orient_matrix_UB_23      0.1069548000
_diffrn_orient_matrix_UB_31      -0.0116836000
_diffrn_orient_matrix_UB_32      0.2764769000
_diffrn_orient_matrix_UB_33      -0.0301974000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2199
_reflns_number_total             2301
_reflns_odcompleteness_completeness 97.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0673P)²+0.0484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C12(H12A,H12B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C17(H17), C6(H6), C14(H14), C18(H18), C15(H15), C3(H3),
 C16(H16), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.46944(15) 0.0911(3) 0.12687(10) 0.0312(4) Uani 1 d . . .
O3 O 0.16352(14) 0.3714(3) 0.17586(11) 0.0336(4) Uani 1 d . . .
O2 O 0.22063(14) 0.4750(4) 0.04761(10) 0.0437(5) Uani 1 d . . .
N1 N 0.68678(16) 0.5752(4) 0.10359(12) 0.0271(4) Uani 1 d . . .
N2 N 0.47886(15) 0.5001(4) 0.16433(11) 0.0237(4) Uani 1 d . . .
H2 H 0.5128 0.6432 0.1617 0.028 Uiso 1 calc . . R
C8 C 0.51718(19) 0.2977(4) 0.12686(14) 0.0244(5) Uani 1 d . . .
C13 C 0.51163(19) 0.7119(4) 0.35784(14) 0.0245(4) Uani 1 d . . .
C10 C 0.24740(19) 0.4433(5) 0.13309(14) 0.0274(5) Uani 1 d . . .
C1 C 0.79169(18) 0.6115(4) 0.18888(14) 0.0254(5) Uani 1 d . . .
C9 C 0.38024(18) 0.4757(4) 0.20904(14) 0.0236(4) Uani 1 d . . .
H9 H 0.3992 0.3249 0.2491 0.028 Uiso 1 calc . . R
C12 C 0.38394(19) 0.6984(4) 0.27596(14) 0.0263(5) Uani 1 d . . .
H12A H 0.3706 0.8514 0.2387 0.032 Uiso 1 calc . . R
H12B H 0.3144 0.6826 0.3025 0.032 Uiso 1 calc . . R
C2 C 0.8124(2) 0.4597(5) 0.26979(15) 0.0295(5) Uani 1 d . . .
H2A H 0.7562 0.3289 0.2681 0.035 Uiso 1 calc . . R
C17 C 0.6613(2) 0.5453(5) 0.50636(15) 0.0302(5) Uani 1 d . . .
H17 H 0.6817 0.4252 0.5549 0.036 Uiso 1 calc . . R
C6 C 0.8769(2) 0.8077(5) 0.19390(16) 0.0308(5) Uani 1 d . . .
H6 H 0.8635 0.9118 0.1407 0.037 Uiso 1 calc . . R
C14 C 0.6003(2) 0.8984(4) 0.36054(15) 0.0288(5) Uani 1 d . . .
H14 H 0.5808 1.0180 0.3118 0.035 Uiso 1 calc . . R
C7 C 0.62249(19) 0.3382(4) 0.08290(14) 0.0271(5) Uani 1 d . . .
H7A H 0.6866 0.2078 0.1060 0.033 Uiso 1 calc . . R
H7B H 0.5848 0.3202 0.0132 0.033 Uiso 1 calc . . R
C18 C 0.5428(2) 0.5356(5) 0.43158(15) 0.0288(5) Uani 1 d . . .
H18 H 0.4841 0.4101 0.4310 0.035 Uiso 1 calc . . R
C15 C 0.7183(2) 0.9080(5) 0.43561(16) 0.0332(5) Uani 1 d . . .
H15 H 0.7772 1.0333 0.4366 0.040 Uiso 1 calc . . R
C3 C 0.9181(2) 0.5045(5) 0.35352(16) 0.0349(5) Uani 1 d . . .
H3 H 0.9318 0.4022 0.4073 0.042 Uiso 1 calc . . R
C16 C 0.7482(2) 0.7322(5) 0.50850(15) 0.0316(5) Uani 1 d . . .
H16 H 0.8267 0.7400 0.5589 0.038 Uiso 1 calc . . R
C5 C 0.9812(2) 0.8493(5) 0.27719(17) 0.0361(5) Uani 1 d . . .
H5 H 1.0376 0.9800 0.2792 0.043 Uiso 1 calc . . R
C4 C 1.0020(2) 0.6984(5) 0.35731(16) 0.0355(5) Uani 1 d . . .
H4 H 1.0720 0.7272 0.4133 0.043 Uiso 1 calc . . R
C11 C 0.0322(2) 0.3351(6) 0.11331(18) 0.0420(6) Uani 1 d . . .
H11A H 0.0048 0.4767 0.0714 0.063 Uiso 1 calc . . GR
H11B H -0.0229 0.3167 0.1518 0.063 Uiso 1 calc . . GR
H11C H 0.0271 0.1877 0.0751 0.063 Uiso 1 calc . . GR
H1 H 0.692(2) 0.666(6) 0.051(2) 0.032(7) Uiso 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
O1 C8 1.226(3) . ?
O3 C10 1.333(3) . ?
O3 C11 1.440(3) . ?
O2 C10 1.199(3) . ?
N1 C1 1.401(2) . ?
N1 C7 1.437(3) . ?
N1 H1 0.92(3) . ?
N2 H2 0.8600 . ?
N2 C8 1.346(3) . ?
N2 C9 1.447(2) . ?
C8 C7 1.516(3) . ?
C13 C12 1.512(3) . ?
C13 C14 1.388(3) . ?
C13 C18 1.390(3) . ?
C10 C9 1.520(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.394(3) . ?
C9 H9 0.9800 . ?
C9 C12 1.537(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C2 H2A 0.9300 . ?
C2 C3 1.399(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(3) . ?
C17 C16 1.378(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.384(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C18 H18 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.379(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C16 H16 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C10 O3 C11 116.26(17) . . ?
C1 N1 C7 120.71(18) . . ?
C1 N1 H1 114.2(16) . . ?
C7 N1 H1 116.8(17) . . ?
C8 N2 H2 120.2 . . ?
C8 N2 C9 119.68(18) . . ?
C9 N2 H2 120.2 . . ?
O1 C8 N2 122.49(19) . . ?
O1 C8 C7 121.10(19) . . ?
N2 C8 C7 116.41(18) . . ?
C14 C13 C12 120.87(19) . . ?
C14 C13 C18 118.72(19) . . ?
C18 C13 C12 120.41(19) . . ?
O3 C10 C9 109.50(15) . . ?
O2 C10 O3 124.46(18) . . ?
O2 C10 C9 126.04(18) . . ?
C2 C1 N1 122.0(2) . . ?
C2 C1 C6 118.74(19) . . ?
C6 C1 N1 119.3(2) . . ?
N2 C9 C10 111.05(15) . . ?
N2 C9 H9 107.7 . . ?
N2 C9 C12 110.76(17) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C12 111.71(17) . . ?
C12 C9 H9 107.7 . . ?
C13 C12 C9 111.29(17) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C9 C12 H12A 109.4 . . ?
C9 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.8(2) . . ?
C3 C2 H2A 120.1 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.5(2) . . ?
C15 C14 H14 119.7 . . ?
N1 C7 C8 115.34(18) . . ?
N1 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C8 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C13 C18 C17 120.5(2) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C17 C16 C15 119.76(19) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C8 N2 12.0(2) . . . . ?
N2 C9 C10 O3 167.50(19) . . . . ?
C8 N2 C9 C10 -74.7(2) . . . . ?
C1 N1 C7 C8 85.5(2) . . . . ?
C9 C10 O3 C11 179.4(2) . . . . ?
C7 C8 N2 C9 -178.98(16) . . . . ?

_olex2_date_sample_data_collection 2019-10-30
_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_uk_1
_database_code_depnum_ccdc_archive 'CCDC 2006561'
loop_
_audit_author_name
_audit_author_address
'Debasish Haldar'
;IISER Kolkata
India
;
_audit_update_record             
;
2020-10-15 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2020-10-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            Boc-Gly-Aib-OMe
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H22 N2 O5'
_chemical_formula_sum            'C12 H22 N2 O5'
_chemical_formula_weight         274.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.6077(4)
_cell_length_b                   5.8948(2)
_cell_length_c                   23.3133(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.550(4)
_cell_angle_gamma                90.00
_cell_volume                     1568.25(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.7050
_cell_measurement_theta_min      3.8680
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7274
_diffrn_reflns_theta_full        65.90
_diffrn_reflns_theta_max         65.90
_diffrn_reflns_theta_min         3.87
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     57.00 123.00   1.00    2.00    --   25.52 178.00 150.00   66
  2  ω    -13.00 102.00   1.00    2.00    --   25.52  57.00   0.00  115
  3  ω    -13.00 102.00   1.00    2.00    --   25.52  57.00  90.00  115
  4  ω    100.00 153.00   1.00    2.00    --   66.76 111.00 -30.00   53
  5  ω    100.00 153.00   1.00    2.00    --   66.76 111.00 150.00   53
  6  ω    100.00 153.00   1.00    2.00    --   66.76 111.00  90.00   53
  7  ω    100.00 153.00   1.00    2.00    --   66.76 111.00  60.00   53
  8  ω    -11.00 106.00   1.00    2.00    --   66.76 -61.00  60.00  117
  9  ω    -22.00 155.00   1.00    2.00    --   66.76 -15.00 -60.00  177
 10  ω     57.00 150.00   1.00    2.00    --   66.76 178.00  60.00   93
 11  ω     70.00 178.00   1.00    4.00    --  108.00  65.00 -90.00  108
 12  ω     86.00 178.00   1.00    4.00    --  108.00 138.00  30.00   92
 13  ω    101.00 178.00   1.00    4.00    --  108.00 104.00 -60.00   77
 14  ω     20.00 113.00   1.00    4.00    --  108.00-104.00 120.00   93
 15  ω     33.00 178.00   1.00    4.00    --  108.00  32.00  30.00  145
 16  ω     30.00 148.00   1.00    4.00    --  108.00 -54.00  30.00  118
 17  ω     20.00 113.00   1.00    4.00    --  108.00-104.00  60.00   93
 18  ω     71.00 113.00   1.00    4.00    --  108.00  76.00   9.82   42
 19  ω    147.00 173.00   1.00    4.00    --  108.00  76.00   9.82   26
 20  ω    121.00 147.00   1.00    4.00    --  108.00 104.00-120.00   26
 21  ω     73.00 144.00   1.00    4.00    --  108.00  65.00 -60.00   71
 22  ω     96.00 132.00   1.00    4.00    --  108.00 138.00-180.00   36
 23  ω    104.00 178.00   1.00    4.00    --  108.00 104.00 -30.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054565000
_diffrn_orient_matrix_UB_12      0.1058362000
_diffrn_orient_matrix_UB_13      0.0598668000
_diffrn_orient_matrix_UB_21      -0.1313520000
_diffrn_orient_matrix_UB_22      -0.0582716000
_diffrn_orient_matrix_UB_23      -0.0082962000
_diffrn_orient_matrix_UB_31      0.0305993000
_diffrn_orient_matrix_UB_32      -0.2317208000
_diffrn_orient_matrix_UB_33      0.0294587000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2132
_reflns_number_total             2685
_reflns_odcompleteness_completeness 96.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.267
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0565P)²+0.2467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1307
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C3(H3A,H3B,
 H3C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O3 O 0.16207(10) 0.4107(2) 0.56030(6) 0.0519(3) Uani 1 d . . .
O5 O 0.42418(12) 0.3861(2) 0.57816(7) 0.0667(4) Uani 1 d . . .
O1 O 0.09713(12) 0.5316(3) 0.39584(6) 0.0695(4) Uani 1 d . . .
N1 N 0.08062(12) 0.7285(3) 0.47449(6) 0.0500(4) Uani 1 d . . .
H1 H 0.0067 0.7363 0.4608 0.060 Uiso 1 calc . . R
O2 O 0.26077(12) 0.6770(3) 0.45281(7) 0.0727(5) Uani 1 d . . .
N2 N 0.27101(13) 0.6729(2) 0.61523(6) 0.0483(4) Uani 1 d . . .
H2 H 0.2874 0.8146 0.6204 0.058 Uiso 1 calc . . R
O4 O 0.37642(16) 0.1193(2) 0.63707(8) 0.0849(6) Uani 1 d . . .
C7 C 0.18864(14) 0.6099(3) 0.57020(7) 0.0428(4) Uani 1 d . . .
C6 C 0.12763(16) 0.8024(3) 0.53299(8) 0.0505(4) Uani 1 d . . .
H6A H 0.0646 0.8611 0.5509 0.061 Uiso 1 calc . . R
H6B H 0.1831 0.9244 0.5315 0.061 Uiso 1 calc . . R
C9 C 0.37776(16) 0.3141(3) 0.62230(9) 0.0546(5) Uani 1 d . . .
C5 C 0.15612(16) 0.6467(3) 0.44184(8) 0.0533(5) Uani 1 d . . .
C8 C 0.33390(17) 0.5069(3) 0.65597(8) 0.0526(5) Uani 1 d . . .
C12 C 0.4416(2) 0.6251(4) 0.69123(11) 0.0792(8) Uani 1 d . . .
H12A H 0.4887 0.6862 0.6651 0.119 Uiso 1 calc . . GR
H12B H 0.4869 0.5175 0.7169 0.119 Uiso 1 calc . . GR
H12C H 0.4168 0.7458 0.7138 0.119 Uiso 1 calc . . GR
C4 C 0.1598(2) 0.4183(4) 0.35487(9) 0.0688(6) Uani 1 d . . .
C11 C 0.2557(3) 0.4138(5) 0.69601(11) 0.0872(8) Uani 1 d . . .
H11A H 0.2320 0.5352 0.7187 0.131 Uiso 1 calc . . GR
H11B H 0.2980 0.3023 0.7216 0.131 Uiso 1 calc . . GR
H11C H 0.1875 0.3450 0.6730 0.131 Uiso 1 calc . . GR
C10 C 0.4645(2) 0.2124(5) 0.54243(14) 0.0977(9) Uani 1 d . . .
H10A H 0.4980 0.2828 0.5122 0.147 Uiso 1 calc . . GR
H10B H 0.3995 0.1191 0.5252 0.147 Uiso 1 calc . . GR
H10C H 0.5226 0.1203 0.5663 0.147 Uiso 1 calc . . GR
C3 C 0.2478(3) 0.2500(5) 0.38588(14) 0.1002(9) Uani 1 d . . .
H3A H 0.3099 0.3299 0.4106 0.150 Uiso 1 calc . . GR
H3B H 0.2795 0.1630 0.3576 0.150 Uiso 1 calc . . GR
H3C H 0.2098 0.1502 0.4091 0.150 Uiso 1 calc . . GR
C2 C 0.2172(3) 0.5939(5) 0.32206(12) 0.1063(10) Uani 1 d . . .
H2A H 0.1598 0.7037 0.3051 0.160 Uiso 1 calc . . GR
H2B H 0.2495 0.5211 0.2917 0.160 Uiso 1 calc . . GR
H2C H 0.2787 0.6686 0.3485 0.160 Uiso 1 calc . . GR
C1 C 0.0623(3) 0.2986(6) 0.31453(14) 0.1147(12) Uani 1 d . . .
H1A H 0.0250 0.1925 0.3364 0.172 Uiso 1 calc . . GR
H1B H 0.0939 0.2192 0.2850 0.172 Uiso 1 calc . . GR
H1C H 0.0059 0.4081 0.2965 0.172 Uiso 1 calc . . GR


_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
O3 C7 1.225(2) . ?
O5 C9 1.316(3) . ?
O5 C10 1.451(3) . ?
O1 C5 1.346(2) . ?
O1 C4 1.464(2) . ?
N1 C6 1.440(2) . ?
N1 C5 1.351(2) . ?
O2 C5 1.208(2) . ?
N2 C7 1.337(2) . ?
N2 C8 1.463(2) . ?
O4 C9 1.200(2) . ?
C7 C6 1.522(2) . ?
C9 C8 1.521(3) . ?
C8 C12 1.533(3) . ?
C8 C11 1.519(3) . ?
C4 C3 1.509(3) . ?
C4 C2 1.512(4) . ?
C4 C1 1.508(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
C9 O5 C10 116.28(19) . . ?
C5 O1 C4 120.59(16) . . ?
C5 N1 C6 117.98(15) . . ?
C7 N2 C8 121.62(14) . . ?
O3 C7 N2 122.24(16) . . ?
O3 C7 C6 122.16(15) . . ?
N2 C7 C6 115.58(14) . . ?
N1 C6 C7 111.75(14) . . ?
O5 C9 C8 112.71(16) . . ?
O4 C9 O5 124.2(2) . . ?
O4 C9 C8 123.0(2) . . ?
O1 C5 N1 109.96(16) . . ?
O2 C5 O1 126.06(19) . . ?
O2 C5 N1 123.97(18) . . ?
N2 C8 C9 109.83(16) . . ?
N2 C8 C12 107.77(15) . . ?
N2 C8 C11 110.94(18) . . ?
C9 C8 C12 107.42(17) . . ?
C11 C8 C9 109.96(18) . . ?
C11 C8 C12 110.8(2) . . ?
O1 C4 C3 111.1(2) . . ?
O1 C4 C2 109.6(2) . . ?
O1 C4 C1 102.36(19) . . ?
C3 C4 C2 111.7(2) . . ?
C1 C4 C3 110.9(2) . . ?
C1 C4 C2 110.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 N1 C6 163.57(16) . . . . ?
N1 C6 C7 N2 155.14(16) . . . . ?
N2 C8 C9 O5 43.7(2) . . . . ?
C7 N2 C8 C9 48.4(2) . . . . ?
C6 C7 N2 C8 177.75(16) . . . . ?
C5 N1 C6 C7 -60.7(2) . . . . ?
C8 C9 O5 C10 -177.89(18) . . . . ?
C4 O1 C5 N1 -177.61(18) . . . . ?

_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 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.457
