# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_exp_3552
_audit_block_doi                 10.5517/ccdc.csd.cc1p4k2g
_database_code_depnum_ccdc_archive 'CCDC 1553505'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_cell_formula_units_Z            4
_cell_angle_alpha                103.668(9)
_cell_angle_beta                 90.921(9)
_cell_angle_gamma                102.650(9)
_cell_length_a                   7.0483(8)
_cell_length_b                   12.6910(13)
_cell_length_c                   14.4533(15)
_cell_volume                     1222.6(2)
_cell_measurement_temperature    294.83(16)
_cell_measurement_reflns_used    1528
_cell_measurement_theta_min      3.2120
_cell_measurement_theta_max      24.2560
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.29
_diffrn_ambient_temperature      294.83(16)
_diffrn_measurement_device_type  agilent
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10130
_diffrn_reflns_theta_full        24.9977
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.91
_exptl_crystal_description       block
_exptl_absorpt_coefficient_mu    0.097
_exptl_crystal_F_000             552.2653
_exptl_crystal_density_diffrn    1.4357

_refine_diff_density_max         0.3778
_refine_diff_density_min         -0.3355
_refine_diff_density_rms         0.0939
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0624
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.0040
_refine_ls_goodness_of_fit_ref   1.0541
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0541
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1270
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              14
_reflns_limit_k_min              -15
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2521
_reflns_number_total             4294
_reflns_threshold_expression     I>=2u(I)
_space_group_IT_number           2
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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
N2 N 0.2563(3) 0.57944(17) -0.04965(15) 0.0395(6) Uani 1.000000
N3 N 0.1911(3) 0.93776(18) 0.58544(17) 0.0462(6) Uani 1.000000
N4 N 0.2195(3) 0.39492(18) -0.10487(16) 0.0450(6) Uani 1.000000
N5 N 0.2445(3) 1.12150(18) 0.65020(18) 0.0514(7) Uani 1.000000
O6 O 0.1278(3) 0.75142(17) 0.53131(15) 0.0735(7) Uani 1.000000
C7 C 0.3652(4) 1.0951(3) 0.3002(2) 0.0522(8) Uani 1.000000
C8 C 0.2422(4) 0.4756(2) -0.02901(19) 0.0376(7) Uani 1.000000
C9 C 0.2379(4) 0.5586(2) -0.14932(19) 0.0407(7) Uani 1.000000
C10 C 0.3203(4) 0.9890(2) 0.3139(2) 0.0515(8) Uani 1.000000
H10 H 0.3175(4) 0.9282(2) 0.2628(2) 0.0618(10) Uiso 1.000000
C11 C 0.2560(4) 0.4684(2) 0.06851(18) 0.0378(7) Uani 1.000000
C13 C 0.2406(4) 1.0451(2) 0.5720(2) 0.0451(7) Uani 1.000000
C15 C 0.2789(4) 0.5638(2) 0.14117(19) 0.0404(7) Uani 1.000000
C16 C 0.3283(4) 1.1695(2) 0.4639(2) 0.0523(8) Uani 1.000000
H16 H 0.3306(4) 1.2305(2) 0.5147(2) 0.0627(10) Uiso 1.000000
C17 C 0.2795(4) 0.9723(2) 0.4033(2) 0.0448(8) Uani 1.000000
C18 C 0.2284(5) 0.8573(3) 0.4176(2) 0.0528(9) Uani 1.000000
C19 C 0.2155(4) 0.4444(2) -0.1814(2) 0.0422(7) Uani 1.000000
C20 C 0.2470(4) 0.3667(2) 0.0907(2) 0.0466(8) Uani 1.000000
H20 H 0.2314(4) 0.3022(2) 0.0419(2) 0.0559(9) Uiso 1.000000
C21 C 0.1933(4) 0.3947(2) -0.2776(2) 0.0503(8) Uani 1.000000
H21 H 0.1795(4) 0.3182(2) -0.3000(2) 0.0604(10) Uiso 1.000000
C22 C 0.2911(4) 0.5568(2) 0.2350(2) 0.0476(8) Uani 1.000000
H22 H 0.3064(4) 0.6209(2) 0.2843(2) 0.0572(9) Uiso 1.000000
C23 C 0.2832(4) 1.0622(2) 0.4786(2) 0.0440(7) Uani 1.000000
C24 C 0.2810(4) 0.4560(2) 0.2557(2) 0.0467(8) Uani 1.000000
O25 O 0.2929(4) 0.76505(17) -0.00644(15) 0.0884(8) Uani 1.000000
C26 C 0.1580(4) 0.9496(2) 0.6821(2) 0.0465(8) Uani 1.000000
C27 C 0.1929(4) 1.0639(2) 0.7204(2) 0.0493(8) Uani 1.000000
C28 C 0.2609(4) 0.3606(2) 0.1835(2) 0.0498(8) Uani 1.000000
H28 H 0.2570(4) 0.2925(2) 0.1979(2) 0.0597(10) Uiso 1.000000
C29 C 0.1045(4) 0.8738(2) 0.7368(2) 0.0561(9) Uani 1.000000
H29 H 0.0811(4) 0.7975(2) 0.7104(2) 0.0673(10) Uiso 1.000000
C30 C 0.2818(4) 0.6797(2) 0.0176(2) 0.0503(8) Uani 1.000000
C31 C 0.1770(4) 0.8415(2) 0.5146(2) 0.0521(8) Uani 1.000000
C32 C 0.3690(4) 1.1858(2) 0.3757(2) 0.0564(8) Uani 1.000000
H32 H 0.3992(4) 1.2575(2) 0.3665(2) 0.0677(10) Uiso 1.000000
C33 C 0.1921(4) 0.4613(3) -0.3396(2) 0.0564(9) Uani 1.000000
H33 H 0.1746(4) 0.4291(3) -0.4049(2) 0.0677(11) Uiso 1.000000
C34 C 0.2415(4) 0.6264(2) -0.2110(2) 0.0524(8) Uani 1.000000
H34 H 0.2599(4) 0.7032(2) -0.1889(2) 0.0629(10) Uiso 1.000000
C35 C 0.2165(4) 0.5752(3) -0.3072(2) 0.0553(9) Uani 1.000000
H35 H 0.2160(4) 0.6182(3) -0.3511(2) 0.0664(10) Uiso 1.000000
C36 C 0.1731(4) 1.1056(3) 0.8164(2) 0.0597(9) Uani 1.000000
H36 H 0.1944(4) 1.1819(3) 0.8428(2) 0.0716(11) Uiso 1.000000
C37 C 0.0875(4) 0.9168(3) 0.8320(2) 0.0652(10) Uani 1.000000
H37 H 0.0528(4) 0.8682(3) 0.8713(2) 0.0782(12) Uiso 1.000000
C38 C 0.1207(4) 1.0305(3) 0.8711(2) 0.0648(10) Uani 1.000000
H38 H 0.1072(4) 1.0565(3) 0.9359(2) 0.0777(11) Uiso 1.000000
C39 C 0.3097(5) 0.5361(3) 0.4232(2) 0.0770(11) Uani 1.000000
H39a H 0.2011(16) 0.5695(10) 0.4194(9) 0.1154(16) Uiso 1.000000
H39b H 0.313(3) 0.5143(4) 0.4824(2) 0.1154(16) Uiso 1.000000
H39c H 0.4286(15) 0.5889(8) 0.4201(9) 0.1154(16) Uiso 1.000000
C40 C 0.4029(5) 1.0315(3) 0.1331(2) 0.0773(11) Uani 1.000000
H40a H 0.440(3) 1.0618(3) 0.0795(4) 0.1160(16) Uiso 1.000000
H40b H 0.492(2) 0.9880(11) 0.1447(6) 0.1160(16) Uiso 1.000000
H40c H 0.2735(8) 0.9851(11) 0.1198(9) 0.1160(16) Uiso 1.000000
O43 O 0.4071(3) 1.12033(17) 0.21560(16) 0.0673(6) Uani 1.000000
O1 O 0.2903(3) 0.44097(17) 0.34591(14) 0.0629(6) Uani 1.000000
H18a H 0.314(4) 0.809(2) 0.3922(18) 0.062(9) Uiso 1.000000
C1 C 0.2932(5) 0.6742(2) 0.1197(2) 0.0535(9) Uani 1.000000
H18b H 0.134(4) 0.806(2) 0.369(2) 0.067(10) Uiso 1.000000
H1a H 0.373(4) 0.742(2) 0.1650(17) 0.045(8) Uiso 1.000000
H1b H 0.242(3) 0.7395(16) 0.1703(13) 0.008(5) Uiso 1.000000


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C30 1.381(3) .
N2 C9 1.400(3) .
N2 C8 1.402(3) .
N3 C31 1.380(3) .
N3 C13 1.391(3) .
N3 C26 1.399(3) .
N4 C8 1.292(3) .
N4 C19 1.397(3) .
N5 C13 1.299(3) .
N5 C27 1.394(3) .
O6 C31 1.202(3) .
C7 O43 1.356(3) .
C7 C10 1.376(4) .
C7 C32 1.381(4) .
C8 C11 1.437(3) .
C9 C34 1.375(4) .
C9 C19 1.386(3) .
C10 C17 1.381(4) .
C11 C15 1.379(3) .
C11 C20 1.391(3) .
C13 C23 1.443(4) .
C15 C22 1.383(3) .
C15 C1 1.488(4) .
C16 C32 1.363(4) .
C16 C23 1.396(3) .
C17 C23 1.374(3) .
C17 C18 1.490(4) .
C18 C31 1.501(4) .
C19 C21 1.376(3) .
C20 C28 1.364(3) .
C21 C33 1.370(4) .
C22 C24 1.369(3) .
C24 O1 1.364(3) .
C24 C28 1.378(4) .
O25 C30 1.200(3) .
C26 C29 1.378(4) .
C26 C27 1.389(3) .
C27 C36 1.383(4) .
C29 C37 1.373(4) .
C30 C1 1.496(4) .
C33 C35 1.382(4) .
C34 C35 1.378(4) .
C36 C38 1.372(4) .
C37 C38 1.386(4) .
C39 O1 1.418(3) .
C40 O43 1.429(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
C9 N2 C8 106.1(2) . .
C30 N2 C8 125.1(2) . .
C30 N2 C9 128.9(2) . .
C26 N3 C13 106.2(2) . .
C31 N3 C13 124.9(3) . .
C31 N3 C26 128.9(2) . .
C19 N4 C8 105.5(2) . .
C27 N5 C13 105.4(2) . .
C32 C7 C10 120.1(3) . .
O43 C7 C10 124.9(3) . .
O43 C7 C32 114.9(3) . .
N4 C8 N2 112.7(2) . .
C11 C8 N2 119.9(2) . .
C11 C8 N4 127.4(3) . .
C19 C9 N2 104.7(2) . .
C34 C9 N2 133.1(3) . .
C34 C9 C19 122.2(3) . .
C17 C10 C7 120.4(3) . .
C15 C11 C8 119.6(2) . .
C20 C11 C8 121.0(2) . .
C20 C11 C15 119.5(2) . .
N5 C13 N3 112.9(3) . .
C23 C13 N3 120.2(3) . .
C23 C13 N5 126.9(3) . .
C22 C15 C11 119.6(3) . .
C1 C15 C11 120.8(2) . .
C1 C15 C22 119.6(2) . .
C32 C16 C23 120.7(3) . .
C18 C17 C10 120.2(3) . .
C23 C17 C10 119.7(3) . .
C23 C17 C18 120.1(3) . .
C31 C18 C17 119.0(3) . .
C9 C19 N4 111.0(2) . .
C21 C19 N4 128.7(3) . .
C21 C19 C9 120.3(3) . .
C28 C20 C11 120.6(3) . .
C33 C21 C19 118.0(3) . .
C24 C22 C15 120.2(3) . .
C16 C23 C13 120.6(3) . .
C17 C23 C13 119.9(3) . .
C17 C23 C16 119.5(3) . .
C28 C24 C22 120.5(3) . .
O1 C24 C22 124.3(3) . .
O1 C24 C28 115.1(3) . .
C27 C26 N3 104.9(2) . .
C29 C26 N3 132.9(3) . .
C29 C26 C27 122.3(3) . .
C26 C27 N5 110.7(3) . .
C36 C27 N5 128.9(3) . .
C36 C27 C26 120.3(3) . .
C24 C28 C20 119.6(3) . .
C37 C29 C26 116.7(3) . .
O25 C30 N2 120.7(3) . .
C1 C30 N2 116.0(3) . .
C1 C30 O25 123.3(3) . .
O6 C31 N3 121.0(3) . .
C18 C31 N3 115.9(3) . .
C18 C31 O6 123.2(3) . .
C16 C32 C7 119.6(3) . .
C35 C33 C21 121.4(3) . .
C35 C34 C9 116.9(3) . .
C34 C35 C33 121.3(3) . .
C38 C36 C27 117.6(3) . .
C38 C37 C29 121.7(3) . .
C37 C38 C36 121.5(3) . .
C40 O43 C7 118.8(2) . .
C39 O1 C24 117.7(2) . .
C30 C1 C15 118.6(3) . .


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_exp_5355
_audit_block_doi                 10.5517/ccdc.csd.cc1zqrv9
_database_code_depnum_ccdc_archive 'CCDC 1839132'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C19 H21 F N2 O2'
_chemical_formula_sum            'C19 H21 F N2 O2'
_chemical_formula_weight         328.39
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   6.3592(9)
_cell_length_b                   9.7262(14)
_cell_length_c                   15.058(2)
_cell_angle_alpha                92.739(11)
_cell_angle_beta                 99.147(11)
_cell_angle_gamma                106.484(12)
_cell_volume                     877.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    835
_cell_measurement_theta_max      24.5110
_cell_measurement_theta_min      3.6810
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2428
_exptl_crystal_F_000             348.1823
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.1082
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7221
_diffrn_reflns_theta_full        24.9991
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.35
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  79.00   1.00    8.50    --   15.49  77.00 -30.00   86
  2  ω     22.00  67.00   1.00    8.50    --   15.49  77.00-180.00   45
  3  ω     -3.00  44.00   1.00    8.50    --  -16.12  77.00   0.00   47
  4  ω    -11.00  79.00   1.00    8.50    --   15.49  77.00 120.00   90
  5  ω    -32.00  -6.00   1.00    8.50    --  -16.12  77.00   0.00   26
  6  ω    -37.00  46.00   1.00    8.50    --  -16.12  77.00-120.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0144253000
_diffrn_orient_matrix_UB_12      -0.0326489000
_diffrn_orient_matrix_UB_13      0.0406135000
_diffrn_orient_matrix_UB_21      -0.0475320000
_diffrn_orient_matrix_UB_22      -0.0683970000
_diffrn_orient_matrix_UB_23      -0.0251898000
_diffrn_orient_matrix_UB_31      0.1073156000
_diffrn_orient_matrix_UB_32      -0.0098047000
_diffrn_orient_matrix_UB_33      0.0038186000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1559
_reflns_number_total             3088
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.3768
_refine_diff_density_min         -0.3212
_refine_diff_density_rms         0.0871
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.0830
_refine_ls_goodness_of_fit_ref   1.0409
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0664
_refine_ls_restrained_S_all      1.0409
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0734P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.2011
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00E(H00E), C00F(H00F), C00G(H00G)
2.c Idealised Me refined as rotating group:
 C00K(H00a,H00c,H00d), C00L(H00h,H00i,H00k), C00M(H00l,H00m,H00n), C00N(H00o,
 H00p,H00q), C00O(H00r,H00s,H00t)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
F001 F 0.0929(3) 0.8976(2) 0.44350(12) 0.0709(7) Uani 1.000000 .
O002 O 0.5933(4) 0.6857(2) 0.34719(13) 0.0597(7) Uani 1.000000 .
O003 O 0.7854(4) 0.5340(3) 0.39198(13) 0.0655(8) Uani 1.000000 .
N004 N 0.8493(4) 0.6772(3) 0.65621(16) 0.0468(7) Uani 1.000000 .
N005 N 0.7952(5) 0.8007(3) 0.77450(16) 0.0574(8) Uani 1.000000 .
C006 C 0.6806(5) 0.6681(3) 0.50367(19) 0.0400(8) Uani 1.000000 .
C007 C 0.5383(5) 0.7507(3) 0.53081(19) 0.0415(8) Uani 1.000000 .
C008 C 0.5683(5) 0.7994(3) 0.62307(19) 0.0439(8) Uani 1.000000 .
C009 C 0.8262(5) 0.6328(3) 0.56697(19) 0.0459(8) Uani 1.000000 .
H009 H 0.9126(5) 0.5772(3) 0.54948(19) 0.0551(10) Uiso 1.000000 R
C00A C 0.7321(5) 0.7634(3) 0.6868(2) 0.0465(8) Uani 1.000000 .
C00B C 0.3700(5) 0.7846(3) 0.4712(2) 0.0484(9) Uani 1.000000 .
H00B H 0.3407(5) 0.7521(3) 0.4101(2) 0.0581(10) Uiso 1.000000 R
C00C C 0.2513(5) 0.8651(4) 0.5035(2) 0.0510(9) Uani 1.000000 .
C00D C 0.6925(6) 0.6213(4) 0.4101(2) 0.0491(8) Uani 1.000000 .
C00E C 0.4408(6) 0.8822(4) 0.6526(2) 0.0549(9) Uani 1.000000 .
H00E H 0.4647(6) 0.9148(4) 0.7135(2) 0.0659(11) Uiso 1.000000 R
C00F C 0.9959(6) 0.6605(4) 0.7304(2) 0.0549(9) Uani 1.000000 .
H00F H 1.0975(6) 0.6079(4) 0.7312(2) 0.0658(11) Uiso 1.000000 R
C00G C 0.2806(6) 0.9161(4) 0.5925(2) 0.0572(10) Uani 1.000000 .
H00G H 0.1955(6) 0.9715(4) 0.6115(2) 0.0686(11) Uiso 1.000000 R
C00H C 0.9611(6) 0.7364(4) 0.8015(2) 0.0563(9) Uani 1.000000 .
C00I C 1.0816(7) 0.7597(5) 0.8981(2) 0.0699(11) Uani 1.000000 .
C00J C 0.6040(7) 0.6512(5) 0.2529(2) 0.0719(12) Uani 1.000000 .
H00J H 0.5867(7) 0.5481(5) 0.2418(2) 0.0863(14) Uiso 1.000000 R
C00K C 0.9137(8) 0.7097(6) 0.9600(2) 0.1037(17) Uani 1.000000 .
H00a H 0.807(3) 0.763(2) 0.9525(16) 0.156(3) Uiso 1.000000 GR
H00c H 0.838(4) 0.6087(9) 0.9450(15) 0.156(3) Uiso 1.000000 GR
H00d H 0.9899(10) 0.726(3) 1.0217(3) 0.156(3) Uiso 1.000000 GR
C00L C 0.4108(8) 0.6866(6) 0.1984(3) 0.1138(18) Uani 1.000000 .
H00h H 0.2748(9) 0.632(3) 0.2158(17) 0.171(3) Uiso 1.000000 GR
H00i H 0.429(3) 0.7877(8) 0.2092(18) 0.171(3) Uiso 1.000000 GR
H00k H 0.405(4) 0.662(4) 0.1353(3) 0.171(3) Uiso 1.000000 GR
C00M C 1.2540(8) 0.6777(6) 0.9094(3) 0.1156(19) Uani 1.000000 .
H00l H 1.1806(9) 0.5766(7) 0.894(2) 0.173(3) Uiso 1.000000 GR
H00m H 1.359(3) 0.711(3) 0.8702(18) 0.173(3) Uiso 1.000000 GR
H00n H 1.331(4) 0.694(3) 0.9710(6) 0.173(3) Uiso 1.000000 GR
C00N C 1.1960(8) 0.9211(6) 0.9224(3) 0.1152(18) Uani 1.000000 .
H00o H 1.308(4) 0.9537(9) 0.8857(17) 0.173(3) Uiso 1.000000 GR
H00p H 1.0873(11) 0.9725(7) 0.912(2) 0.173(3) Uiso 1.000000 GR
H00q H 1.265(5) 0.9383(7) 0.9850(6) 0.173(3) Uiso 1.000000 GR
C00O C 0.8229(8) 0.7364(6) 0.2342(3) 0.121(2) Uani 1.000000 .
H00r H 0.843(3) 0.8371(7) 0.248(2) 0.182(3) Uiso 1.000000 GR
H00s H 0.9396(9) 0.709(3) 0.2709(17) 0.182(3) Uiso 1.000000 GR
H00t H 0.828(2) 0.718(3) 0.1716(6) 0.182(3) Uiso 1.000000 GR


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
F001 C00C 1.360(3) . ?
O002 C00D 1.333(3) . ?
O002 C00J 1.460(3) . ?
O003 C00D 1.207(4) . ?
N004 C009 1.364(3) . ?
N004 C00A 1.378(4) . ?
N004 C00F 1.384(3) . ?
N005 C00A 1.318(3) . ?
N005 C00H 1.390(4) . ?
C006 C007 1.460(4) . ?
C006 C009 1.347(4) . ?
C006 C00D 1.480(4) . ?
C007 C008 1.412(4) . ?
C007 C00B 1.408(4) . ?
C008 C00A 1.432(4) . ?
C008 C00E 1.398(4) . ?
C009 H009 0.9300 . ?
C00B H00B 0.9300 . ?
C00B C00C 1.354(4) . ?
C00C C00G 1.373(4) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.375(4) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.354(4) . ?
C00G H00G 0.9300 . ?
C00H C00I 1.507(4) . ?
C00I C00K 1.521(5) . ?
C00I C00M 1.522(5) . ?
C00I C00N 1.529(6) . ?
C00J H00J 0.9800 . ?
C00J C00L 1.499(5) . ?
C00J C00O 1.482(6) . ?
C00K H00a 0.9600 . ?
C00K H00c 0.9600 . ?
C00K H00d 0.9600 . ?
C00L H00h 0.9600 . ?
C00L H00i 0.9600 . ?
C00L H00k 0.9600 . ?
C00M H00l 0.9600 . ?
C00M H00m 0.9600 . ?
C00M H00n 0.9600 . ?
C00N H00o 0.9600 . ?
C00N H00p 0.9600 . ?
C00N H00q 0.9600 . ?
C00O H00r 0.9600 . ?
C00O H00s 0.9600 . ?
C00O H00t 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
C00J O002 C00D 118.0(3) . . ?
C00A N004 C009 122.6(3) . . ?
C00F N004 C009 130.4(3) . . ?
C00F N004 C00A 106.7(2) . . ?
C00H N005 C00A 105.2(3) . . ?
C009 C006 C007 119.8(3) . . ?
C00D C006 C007 126.6(3) . . ?
C00D C006 C009 113.6(3) . . ?
C008 C007 C006 118.4(3) . . ?
C00B C007 C006 124.5(3) . . ?
C00B C007 C008 117.2(3) . . ?
C00A C008 C007 119.3(3) . . ?
C00E C008 C007 120.8(3) . . ?
C00E C008 C00A 119.9(3) . . ?
C006 C009 N004 121.2(3) . . ?
H009 C009 N004 119.39(17) . . ?
H009 C009 C006 119.39(17) . . ?
N005 C00A N004 111.4(3) . . ?
C008 C00A N004 118.5(3) . . ?
C008 C00A N005 130.1(3) . . ?
H00B C00B C007 120.25(18) . . ?
C00C C00B C007 119.5(3) . . ?
C00C C00B H00B 120.25(19) . . ?
C00B C00C F001 117.8(3) . . ?
C00G C00C F001 117.9(3) . . ?
C00G C00C C00B 124.3(3) . . ?
O003 C00D O002 122.8(3) . . ?
C006 C00D O002 113.9(3) . . ?
C006 C00D O003 123.3(3) . . ?
H00E C00E C008 119.65(18) . . ?
C00G C00E C008 120.7(3) . . ?
C00G C00E H00E 119.65(19) . . ?
H00F C00F N004 127.04(17) . . ?
C00H C00F N004 105.9(3) . . ?
C00H C00F H00F 127.0(2) . . ?
C00E C00G C00C 117.4(3) . . ?
H00G C00G C00C 121.3(2) . . ?
H00G C00G C00E 121.29(19) . . ?
C00F C00H N005 110.8(3) . . ?
C00I C00H N005 120.8(3) . . ?
C00I C00H C00F 128.4(3) . . ?
C00K C00I C00H 109.4(3) . . ?
C00M C00I C00H 110.1(3) . . ?
C00M C00I C00K 110.4(4) . . ?
C00N C00I C00H 108.5(3) . . ?
C00N C00I C00K 108.3(4) . . ?
C00N C00I C00M 110.1(4) . . ?
H00J C00J O002 109.70(18) . . ?
C00L C00J O002 105.4(3) . . ?
C00L C00J H00J 109.7(3) . . ?
C00O C00J O002 108.9(3) . . ?
C00O C00J H00J 109.7(3) . . ?
C00O C00J C00L 113.3(4) . . ?
H00a C00K C00I 109.5 . . ?
H00c C00K C00I 109.5 . . ?
H00c C00K H00a 109.5 . . ?
H00d C00K C00I 109.5 . . ?
H00d C00K H00a 109.5 . . ?
H00d C00K H00c 109.5 . . ?
H00h C00L C00J 109.5 . . ?
H00i C00L C00J 109.5 . . ?
H00i C00L H00h 109.5 . . ?
H00k C00L C00J 109.5 . . ?
H00k C00L H00h 109.5 . . ?
H00k C00L H00i 109.5 . . ?
H00l C00M C00I 109.5 . . ?
H00m C00M C00I 109.5 . . ?
H00m C00M H00l 109.5 . . ?
H00n C00M C00I 109.5 . . ?
H00n C00M H00l 109.5 . . ?
H00n C00M H00m 109.5 . . ?
H00o C00N C00I 109.5 . . ?
H00p C00N C00I 109.5 . . ?
H00p C00N H00o 109.5 . . ?
H00q C00N C00I 109.5 . . ?
H00q C00N H00o 109.5 . . ?
H00q C00N H00p 109.5 . . ?
H00r C00O C00J 109.5 . . ?
H00s C00O C00J 109.5 . . ?
H00s C00O H00r 109.5 . . ?
H00t C00O C00J 109.5 . . ?
H00t C00O H00r 109.5 . . ?
H00t C00O H00s 109.5 . . ?

_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 2.379
_oxdiff_exptl_absorpt_empirical_full_min 0.577
####################################################################### 
# 
# 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_exp_4102
_audit_block_doi                 10.5517/ccdc.csd.cc1pk84n
_database_code_depnum_ccdc_archive 'CCDC 1565721'
_audit_update_record             
;
2017-07-31 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_cell_formula_units_Z            4
_cell_angle_alpha                90
_cell_angle_beta                 106.980(7)
_cell_angle_gamma                90
_cell_length_a                   9.8482(6)
_cell_length_b                   12.1953(6)
_cell_length_c                   15.5327(10)
_cell_volume                     1784.18(18)
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1972
_cell_measurement_theta_min      3.3750
_cell_measurement_theta_max      26.8630
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.39
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8434
_diffrn_reflns_theta_full        24.9978
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_F_000             712.3504
_exptl_crystal_density_diffrn    1.2522
_exptl_crystal_description       bolck

_refine_diff_density_max         0.2065
_refine_diff_density_min         -0.2235
_refine_diff_density_rms         0.0411
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0445
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.0751
_refine_ls_goodness_of_fit_ref   1.0693
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0693
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1153
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.4337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -7
_reflns_number_gt                2422
_reflns_number_total             3147
_reflns_threshold_expression     I>=2u(I)
_space_group_IT_number           14
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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
C6 C 0.13251(18) 0.23234(14) 0.60438(12) 0.0460(4) Uani 1.000000
C8 C 0.21683(19) 0.16624(15) 0.56778(12) 0.0489(5) Uani 1.000000
C9 C 0.16202(18) 0.11698(14) 0.82197(12) 0.0446(4) Uani 1.000000
C11 C 0.0930(2) 0.21635(14) 0.82537(13) 0.0507(5) Uani 1.000000
C12 C 0.1864(2) 0.04122(17) 0.89185(14) 0.0595(5) Uani 1.000000
H12 H 0.2316(2) -0.02519(17) 0.88953(14) 0.0714(6) Uiso 1.000000
C15 C 0.1404(3) 0.0692(2) 0.96453(15) 0.0756(7) Uani 1.000000
H15 H 0.1548(3) 0.0201(2) 1.01221(15) 0.0908(8) Uiso 1.000000
C16 C 0.0459(2) 0.31223(16) 0.55158(14) 0.0616(6) Uani 1.000000
H16 H -0.0116(2) 0.35551(16) 0.57578(14) 0.0739(7) Uiso 1.000000
C17 C 0.2156(2) 0.1834(2) 0.47926(13) 0.0683(6) Uani 1.000000
H17 H 0.2729(2) 0.1409(2) 0.45445(13) 0.0820(7) Uiso 1.000000
C19 C 0.0734(3) 0.1682(2) 0.96896(17) 0.0839(7) Uani 1.000000
H19 H 0.0443(3) 0.1842(2) 1.01940(17) 0.1006(9) Uiso 1.000000
C20 C 0.0494(3) 0.24254(19) 0.90042(16) 0.0717(6) Uani 1.000000
H20 H 0.0051(3) 0.30906(19) 0.90381(16) 0.0860(8) Uiso 1.000000
C21 C 0.0453(3) 0.3272(2) 0.46358(16) 0.0776(7) Uani 1.000000
H21 H -0.0123(3) 0.3806(2) 0.42838(16) 0.0931(8) Uiso 1.000000
C23 C 0.1302(3) 0.2629(2) 0.42790(15) 0.0834(8) Uani 1.000000
H23 H 0.1299(3) 0.2733(2) 0.36852(15) 0.1001(9) Uiso 1.000000
N4 N 0.18963(14) 0.11782(10) 0.73947(9) 0.0417(3) Uani 1.000000
C1aa C 0.31209(18) 0.08084(14) 0.62537(12) 0.0475(4) Uani 1.000000
H1aa H 0.32303(18) 0.02121(14) 0.58562(12) 0.0570(5) Uiso 1.000000
C0aa C 0.13316(17) 0.21217(13) 0.69671(12) 0.0422(4) Uani 1.000000
N14 N 0.07661(16) 0.27460(11) 0.74641(11) 0.0514(4) Uani 1.000000
C3 C 0.45829(19) 0.12894(16) 0.66884(12) 0.0499(5) Uani 1.000000
O4 O 0.55855(14) 0.06064(13) 0.66070(11) 0.0796(5) Uani 1.000000
O2 O 0.47963(14) 0.21580(11) 0.70563(10) 0.0653(4) Uani 1.000000
C3aa C 0.7069(2) 0.0875(3) 0.70672(19) 0.0918(9) Uani 1.000000
H3aa H 0.7123(2) 0.1536(3) 0.74338(19) 0.1101(11) Uiso 1.000000
C7 C 0.7791(3) 0.1062(3) 0.6366(2) 0.1077(10) Uani 1.000000
H7a H 0.763(2) 0.0444(8) 0.5966(9) 0.1615(15) Uiso 1.000000
H7b H 0.7416(16) 0.1711(10) 0.6032(10) 0.1615(15) Uiso 1.000000
H7c H 0.8791(4) 0.1150(18) 0.6646(2) 0.1615(15) Uiso 1.000000
O1 O 0.36712(13) -0.00836(9) 0.77053(9) 0.0526(3) Uani 1.000000
H1 H 0.3851(15) -0.0719(6) 0.7605(7) 0.0790(5) Uiso 1.000000
C2 C 0.25452(17) 0.03027(13) 0.69918(12) 0.0448(4) Uani 1.000000
C2aa C 0.1440(2) -0.05737(15) 0.65972(15) 0.0607(6) Uani 1.000000
H2aa H 0.1064(11) -0.0851(8) 0.7059(3) 0.0911(8) Uiso 1.000000
H2ab H 0.0685(7) -0.0261(3) 0.6122(6) 0.0911(8) Uiso 1.000000
H2ac H 0.1872(4) -0.1161(5) 0.6361(8) 0.0911(8) Uiso 1.000000
C4 C 0.7667(3) -0.0073(4) 0.7648(2) 0.1680(19) Uani 1.000000
H4a H 0.724(3) -0.0121(18) 0.8127(14) 0.252(3) Uiso 1.000000
H4b H 0.748(3) -0.0734(5) 0.7297(6) 0.252(3) Uiso 1.000000
H4c H 0.8674(7) 0.0021(15) 0.790(2) 0.252(3) Uiso 1.000000


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C6 C8 1.392(3) .
C6 C16 1.393(3) .
C6 C0aa 1.453(2) .
C8 C17 1.387(3) .
C8 C1aa 1.508(3) .
C9 N4 1.386(2) .
C9 C12 1.392(3) .
C9 C11 1.398(2) .
C11 N14 1.385(2) .
C11 C20 1.392(3) .
C12 C15 1.376(3) .
C15 C19 1.388(3) .
C16 C21 1.377(3) .
C17 C23 1.375(3) .
C19 C20 1.365(3) .
C21 C23 1.375(4) .
N4 C0aa 1.363(2) .
N4 C2 1.474(2) .
C1aa C3 1.518(2) .
C1aa C2 1.548(2) .
C0aa N14 1.318(2) .
C3 O2 1.193(2) .
C3 O4 1.326(2) .
O4 C3aa 1.464(2) .
C3aa C4 1.478(5) .
C3aa C7 1.481(4) .
O1 C2 1.401(2) .
C2 C2aa 1.521(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
C16 C6 C8 120.02(18) . .
C0aa C6 C8 118.28(16) . .
C0aa C6 C16 121.64(17) . .
C17 C8 C6 118.90(18) . .
C1aa C8 C6 119.96(16) . .
C1aa C8 C17 121.09(18) . .
C12 C9 C11 121.40(17) . .
N4 C9 C11 104.92(14) . .
N4 C9 C12 133.67(17) . .
C20 C11 C9 120.18(18) . .
N14 C11 C9 110.08(15) . .
N14 C11 C20 129.73(18) . .
C15 C12 C9 116.9(2) . .
C19 C15 C12 122.1(2) . .
C21 C16 C6 120.1(2) . .
C23 C17 C8 120.6(2) . .
C20 C19 C15 121.0(2) . .
C19 C20 C11 118.4(2) . .
C23 C21 C16 119.9(2) . .
C21 C23 C17 120.6(2) . .
C0aa N4 C9 107.13(13) . .
C2 N4 C9 127.86(14) . .
C2 N4 C0aa 124.76(14) . .
C3 C1aa C8 109.98(15) . .
C2 C1aa C8 114.55(14) . .
C2 C1aa C3 109.24(14) . .
N4 C0aa C6 120.48(15) . .
N14 C0aa C6 126.83(16) . .
N14 C0aa N4 112.60(15) . .
C0aa N14 C11 105.21(14) . .
O4 C3 C1aa 110.53(15) . .
O2 C3 C1aa 124.59(17) . .
O2 C3 O4 124.87(17) . .
C3aa O4 C3 118.56(16) . .
C7 C3aa O4 107.5(2) . .
C4 C3aa O4 106.6(2) . .
C4 C3aa C7 112.2(3) . .
C1aa C2 N4 108.89(13) . .
O1 C2 N4 104.41(13) . .
O1 C2 C1aa 110.09(13) . .
C2aa C2 N4 109.38(14) . .
C2aa C2 C1aa 110.82(15) . .
C2aa C2 O1 112.99(14) . .


####################################################################### 
# 
# 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_exp_5142
_audit_block_doi                 10.5517/ccdc.csd.cc1zhk67
_database_code_depnum_ccdc_archive 'CCDC 1832199'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_audit_creation_date             2018-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C20 H23 F N2 O2'
_chemical_formula_sum            'C20 H23 F N2 O2'
_chemical_formula_weight         342.42
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_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

_symmetry_Int_Tables_number      14
_cell_length_a                   11.9347(6)
_cell_length_b                   13.0246(5)
_cell_length_c                   12.4263(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.805(5)
_cell_angle_gamma                90
_cell_volume                     1780.61(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2057
_cell_measurement_temperature    294.9(2)
_cell_measurement_theta_max      26.1000
_cell_measurement_theta_min      3.8460
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2772
_exptl_crystal_F_000             728.3749
_exptl_crystal_description       block
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8578
_diffrn_reflns_theta_full        24.9999
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.56
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.9974
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0091462000
_diffrn_orient_matrix_UB_12      -0.0081587000
_diffrn_orient_matrix_UB_13      -0.0592254000
_diffrn_orient_matrix_UB_21      -0.0547577000
_diffrn_orient_matrix_UB_22      -0.0266916000
_diffrn_orient_matrix_UB_23      -0.0090890000
_diffrn_orient_matrix_UB_31      -0.0328455000
_diffrn_orient_matrix_UB_32      0.0467699000
_diffrn_orient_matrix_UB_33      -0.0154709000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2174
_reflns_number_total             3129
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.2688
_refine_diff_density_min         -0.3471
_refine_diff_density_rms         0.0661
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.7275
_refine_ls_goodness_of_fit_ref   1.0529
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.0529
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.2200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1239
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C13(H13), C6(H6), C12(H12)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C21(H21a,H21b,H21c), C22(H22a,H22b,H22c), C23(H23a,H23b,
 H23c), C24(H24a,H24b,H24c), C25(H25a,H25b,H25c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O2 O 0.34443(12) 0.59466(11) 0.10454(12) 0.0451(4) Uani 1.000000 .
N3 N 0.04757(14) 0.49967(13) -0.19789(13) 0.0363(4) Uani 1.000000 .
N4 N -0.13546(15) 0.42502(13) -0.26239(13) 0.0391(4) Uani 1.000000 .
O5 O 0.41067(15) 0.43290(13) 0.11454(15) 0.0679(5) Uani 1.000000 .
C6 C 0.17699(19) 0.34748(16) 0.12324(16) 0.0397(5) Uani 1.000000 .
C7 C -0.02834(18) 0.43018(15) -0.17491(16) 0.0340(5) Uani 1.000000 .
C8 C 0.01616(17) 0.37730(15) -0.06526(15) 0.0330(5) Uani 1.000000 .
C9 C 0.13470(18) 0.39831(15) 0.01512(15) 0.0344(5) Uani 1.000000 .
C10 C 0.20759(17) 0.47358(15) -0.01524(16) 0.0351(5) Uani 1.000000 .
C11 C 0.46080(19) 0.62769(18) 0.19347(18) 0.0514(6) Uani 1.000000 .
C12 C -0.01939(19) 0.53947(17) -0.30746(16) 0.0410(5) Uani 1.000000 .
C13 C -0.0148(2) 0.25922(17) 0.06964(19) 0.0473(6) Uani 1.000000 .
C14 C -0.12999(18) 0.49383(16) -0.34469(16) 0.0381(5) Uani 1.000000 .
C15 C 0.2332(2) 0.59769(19) -0.16178(18) 0.0547(7) Uani 1.000000 .
C16 C -0.23931(19) 0.51309(17) -0.45644(16) 0.0428(5) Uani 1.000000 .
C17 C 0.16504(18) 0.52211(16) -0.11979(17) 0.0391(5) Uani 1.000000 .
C18 C -0.05731(18) 0.30751(16) -0.03646(17) 0.0424(5) Uani 1.000000 .
C19 C 0.1020(2) 0.28085(17) 0.14679(17) 0.0437(6) Uani 1.000000 .
C20 C 0.33260(19) 0.49599(17) 0.07332(17) 0.0408(5) Uani 1.000000 .
C21 C -0.3392(2) 0.5633(2) -0.4277(2) 0.0671(8) Uani 1.000000 .
C22 C -0.2874(2) 0.4123(2) -0.5193(2) 0.0728(8) Uani 1.000000 .
C23 C -0.2047(2) 0.5841(2) -0.5356(2) 0.0816(9) Uani 1.000000 .
C24 C 0.4298(3) 0.7080(2) 0.2637(2) 0.0722(8) Uani 1.000000 .
C25 C 0.5394(2) 0.6663(3) 0.1337(2) 0.0883(10) Uani 1.000000 .
F1 F 0.14426(12) 0.23111(11) 0.25115(10) 0.0644(4) Uani 1.000000 .
H18 H -0.13562(18) 0.29393(16) -0.08993(17) 0.0508(6) Uiso 1.000000 R
H13 H -0.0633(2) 0.21306(17) 0.08924(19) 0.0568(7) Uiso 1.000000 R
H6 H 0.25520(19) 0.35930(16) 0.17789(16) 0.0476(6) Uiso 1.000000 R
H11 H 0.50049(19) 0.56947(18) 0.24375(18) 0.0617(7) Uiso 1.000000 R
H12 H 0.00650(19) 0.58804(17) -0.34765(16) 0.0493(6) Uiso 1.000000 R
H15a H 0.2338(12) 0.5750(6) -0.2351(7) 0.0820(10) Uiso 1.000000 GR
H15b H 0.1944(8) 0.6636(3) -0.1718(12) 0.0820(10) Uiso 1.000000 GR
H15c H 0.3152(4) 0.6031(9) -0.1055(7) 0.0820(10) Uiso 1.000000 GR
H21a H -0.3569(11) 0.5215(7) -0.3727(12) 0.1007(11) Uiso 1.000000 GR
H21b H -0.3128(6) 0.6299(6) -0.3945(14) 0.1007(11) Uiso 1.000000 GR
H21c H -0.4110(5) 0.5702(12) -0.4977(3) 0.1007(11) Uiso 1.000000 GR
H22a H -0.2271(6) 0.3818(7) -0.5427(13) 0.1092(12) Uiso 1.000000 GR
H22b H -0.3055(15) 0.3663(5) -0.4678(5) 0.1092(12) Uiso 1.000000 GR
H22c H -0.3600(9) 0.4250(3) -0.5871(9) 0.1092(12) Uiso 1.000000 GR
H23a H -0.1757(17) 0.6481(6) -0.4963(7) 0.1223(14) Uiso 1.000000 GR
H23b H -0.1419(13) 0.5527(7) -0.5545(14) 0.1223(14) Uiso 1.000000 GR
H23c H -0.2746(5) 0.5964(12) -0.6060(8) 0.1223(14) Uiso 1.000000 GR
H24a H 0.3969(15) 0.7671(6) 0.2158(5) 0.1083(12) Uiso 1.000000 GR
H24b H 0.3709(12) 0.6811(5) 0.2912(13) 0.1083(12) Uiso 1.000000 GR
H24c H 0.5019(4) 0.7272(10) 0.3292(9) 0.1083(12) Uiso 1.000000 GR
H25a H 0.5547(16) 0.6118(5) 0.0892(15) 0.1324(15) Uiso 1.000000 GR
H25b H 0.4991(9) 0.7218(11) 0.0825(14) 0.1324(15) Uiso 1.000000 GR
H25c H 0.6152(8) 0.6902(15) 0.1910(3) 0.1324(15) Uiso 1.000000 GR


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
O2 C11 1.465(2) . ?
O2 C20 1.334(2) . ?
N3 C7 1.386(2) . ?
N3 C12 1.385(2) . ?
N3 C17 1.392(2) . ?
N4 C7 1.320(2) . ?
N4 C14 1.380(2) . ?
O5 C20 1.198(2) . ?
C6 C9 1.404(3) . ?
C6 C19 1.357(3) . ?
C7 C8 1.432(3) . ?
C8 C9 1.407(3) . ?
C8 C18 1.402(3) . ?
C9 C10 1.454(3) . ?
C10 C17 1.354(3) . ?
C10 C20 1.500(3) . ?
C11 C24 1.497(3) . ?
C11 C25 1.492(3) . ?
C12 C14 1.355(3) . ?
C13 C18 1.368(3) . ?
C13 C19 1.380(3) . ?
C14 C16 1.513(3) . ?
C15 C17 1.494(3) . ?
C16 C21 1.518(3) . ?
C16 C22 1.522(3) . ?
C16 C23 1.520(3) . ?
C19 F1 1.360(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
C20 O2 C11 117.71(17) . . ?
C12 N3 C7 105.83(15) . . ?
C17 N3 C7 123.74(16) . . ?
C17 N3 C12 130.41(17) . . ?
C14 N4 C7 105.56(16) . . ?
C19 C6 C9 119.02(19) . . ?
N4 C7 N3 111.42(16) . . ?
C8 C7 N3 118.61(16) . . ?
C8 C7 N4 129.97(18) . . ?
C9 C8 C7 118.81(17) . . ?
C18 C8 C7 121.10(17) . . ?
C18 C8 C9 120.07(18) . . ?
C8 C9 C6 118.50(18) . . ?
C10 C9 C6 122.45(18) . . ?
C10 C9 C8 119.02(17) . . ?
C17 C10 C9 121.59(17) . . ?
C20 C10 C9 117.76(17) . . ?
C20 C10 C17 120.64(18) . . ?
C24 C11 O2 105.60(19) . . ?
C25 C11 O2 108.60(18) . . ?
C25 C11 C24 113.6(2) . . ?
C14 C12 N3 106.62(18) . . ?
C19 C13 C18 118.2(2) . . ?
C12 C14 N4 110.57(18) . . ?
C16 C14 N4 121.07(18) . . ?
C16 C14 C12 128.31(19) . . ?
C21 C16 C14 109.38(16) . . ?
C22 C16 C14 110.33(18) . . ?
C22 C16 C21 108.5(2) . . ?
C23 C16 C14 109.94(18) . . ?
C23 C16 C21 109.0(2) . . ?
C23 C16 C22 109.64(19) . . ?
C10 C17 N3 118.21(18) . . ?
C15 C17 N3 115.62(17) . . ?
C15 C17 C10 126.16(18) . . ?
C13 C18 C8 120.58(19) . . ?
C13 C19 C6 123.60(19) . . ?
F1 C19 C6 118.58(19) . . ?
F1 C19 C13 117.81(19) . . ?
O5 C20 O2 124.00(19) . . ?
C10 C20 O2 111.35(18) . . ?
C10 C20 O5 124.59(19) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.636
_oxdiff_exptl_absorpt_empirical_full_min 0.795
####################################################################### 
# 
# 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_exp_3995
_audit_block_doi                 10.5517/ccdc.csd.cc1p4kds
_database_code_depnum_ccdc_archive 'CCDC 1553515'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_cell_formula_units_Z            2
_cell_angle_alpha                100.641(16)
_cell_angle_beta                 104.19(2)
_cell_angle_gamma                113.52(2)
_cell_length_a                   10.711(3)
_cell_length_b                   11.136(2)
_cell_length_c                   13.512(3)
_cell_volume                     1358.4(6)
_cell_measurement_reflns_used    1208
_cell_measurement_theta_min      3.3930
_cell_measurement_theta_max      20.2180
_cell_measurement_temperature    291(2)
_diffrn_ambient_temperature      291(2)
_chemical_formula_moiety         '2(C16 H14 N2 O), H2 O'
_chemical_formula_sum            'C32 H30 N4 O3'
_chemical_formula_weight         518.62
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9979
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.1301
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10745
_diffrn_reflns_theta_full        24.9931
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.05
_diffrn_measurement_device_type  agilent
_exptl_crystal_description       block
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_F_000             548.2428
_exptl_crystal_density_diffrn    1.2678

_refine_diff_density_max         0.5131
_refine_diff_density_min         -0.5141
_refine_diff_density_rms         0.1304
_refine_ls_R_factor_all          0.1746
_refine_ls_R_factor_gt           0.0960
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             6.6764
_refine_ls_goodness_of_fit_ref   1.1109
_refine_ls_matrix_type           full
_refine_ls_number_constraints    53
_refine_ls_number_parameters     359
_refine_ls_number_reflns         4779
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.1107
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.1936
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.7529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2716
_reflns_number_total             4779
_reflns_threshold_expression     I>=2u(I)
_space_group_IT_number           2
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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
C13 C 0.4057(6) 0.1863(6) 0.3719(4) 0.0618(14) Uani 1.000000
H13 H 0.4159(6) 0.1659(6) 0.3053(4) 0.0742(16) Uiso 1.000000
C14 C 0.2927(5) 0.1163(4) 0.4963(3) 0.0434(11) Uani 1.000000
C15 C 0.4138(5) 0.5790(5) 0.1067(4) 0.0516(12) Uani 1.000000
C16 C 0.2903(5) 0.4584(5) 0.0416(4) 0.0523(12) Uani 1.000000
C17 C 0.3040(5) 0.0845(5) 0.3959(4) 0.0471(11) Uani 1.000000
C20 C 0.3802(5) 0.2479(4) 0.5681(4) 0.0527(12) Uani 1.000000
H20 H 0.3724(5) 0.2695(4) 0.6355(4) 0.0632(15) Uiso 1.000000
C26 C 0.4915(6) 0.3160(6) 0.4433(5) 0.0680(15) Uani 1.000000
H26 H 0.5591(6) 0.3833(6) 0.4254(5) 0.0816(18) Uiso 1.000000
C29 C 0.4779(6) 0.3466(5) 0.5411(5) 0.0663(14) Uani 1.000000
H29 H 0.5356(6) 0.4354(5) 0.5897(5) 0.0795(17) Uiso 1.000000
C30 C 0.4208(7) 0.7063(5) 0.1193(5) 0.0776(17) Uani 1.000000
H30 H 0.5042(7) 0.7867(5) 0.1647(5) 0.093(2) Uiso 1.000000
C37 C 0.2955(8) 0.7093(7) 0.0603(6) 0.093(2) Uani 1.000000
H37 H 0.2944(8) 0.7934(7) 0.0663(6) 0.112(2) Uiso 1.000000
C38 C 0.1730(7) 0.5879(7) -0.0072(5) 0.0796(16) Uani 1.000000
H38 H 0.0917(7) 0.5927(7) -0.0466(5) 0.096(2) Uiso 1.000000
O10 O 0.0431(4) -0.2912(3) 0.2919(2) 0.0647(10) Uani 1.000000
H10 H -0.0286(13) -0.2784(18) 0.278(3) 0.0971(15) Uiso 1.000000
N12 N 0.1276(4) -0.1256(3) 0.4584(3) 0.0409(9) Uani 1.000000
C0aa C -0.0377(5) -0.3464(5) 0.4826(4) 0.0581(13) Uani 1.000000
H0aa H -0.0482(5) -0.4083(5) 0.4207(4) 0.0697(16) Uiso 1.000000
C18 C 0.1627(5) -0.1714(5) 0.3642(3) 0.0495(12) Uani 1.000000
N1aa N 0.5248(4) 0.5469(4) 0.1548(3) 0.0551(11) Uani 1.000000
N2aa N 0.3253(4) 0.3524(3) 0.0514(3) 0.0437(9) Uani 1.000000
C9 C -0.0877(5) -0.3001(5) 0.6438(4) 0.0656(14) Uani 1.000000
H9 H -0.1344(5) -0.3348(5) 0.6895(4) 0.0787(17) Uiso 1.000000
C11 C 0.0651(5) -0.1130(4) 0.6020(3) 0.0433(11) Uani 1.000000
C3aa C -0.0048(5) -0.1610(5) 0.6706(4) 0.0540(13) Uani 1.000000
H3aa H 0.0044(5) -0.1007(5) 0.7328(4) 0.0648(15) Uiso 1.000000
C4aa C -0.1045(5) -0.3901(5) 0.5523(4) 0.0656(14) Uani 1.000000
H4aa H -0.1633(5) -0.4841(5) 0.5369(4) 0.0788(17) Uiso 1.000000
N5aa N 0.1554(4) 0.0193(3) 0.6092(3) 0.0437(9) Uani 1.000000
C1aa C 0.5311(5) 0.3301(5) 0.1492(3) 0.0505(11) Uani 1.000000
C7aa C 0.4538(5) 0.1859(5) 0.0964(3) 0.0557(13) Uani 1.000000
C6aa C 0.4638(5) 0.4146(5) 0.1195(3) 0.0504(11) Uani 1.000000
C8aa C 0.2240(5) 0.2046(5) 0.0203(3) 0.0562(13) Uani 1.000000
C0ba C 0.0469(5) -0.2051(4) 0.5086(3) 0.0421(11) Uani 1.000000
C9aa C 0.1917(5) 0.0073(4) 0.5233(3) 0.0385(10) Uani 1.000000
C1ba C 0.2026(5) -0.0550(5) 0.3171(3) 0.0572(13) Uani 1.000000
H1ba H 0.1139(5) -0.0542(5) 0.2783(3) 0.0687(16) Uiso 1.000000
H1bb H 0.2464(5) -0.0736(5) 0.2651(3) 0.0687(16) Uiso 1.000000
C6 C 0.3143(6) 0.1294(5) 0.0072(4) 0.0627(14) Uani 1.000000
H6a H 0.3338(6) 0.1324(5) -0.0589(4) 0.0752(17) Uiso 1.000000
H6b H 0.2567(6) 0.0332(5) -0.0003(4) 0.0752(17) Uiso 1.000000
C2ba C 0.1680(6) 0.4600(6) -0.0177(4) 0.0702(15) Uani 1.000000
H2ba H 0.0853(6) 0.3789(6) -0.0629(4) 0.0842(18) Uiso 1.000000
O2 O 0.1111(3) 0.1635(3) -0.0737(2) 0.0607(9) Uani 1.000000
H2 H 0.1435(3) 0.184(5) -0.1207(11) 0.0911(13) Uiso 1.000000
C3 C 0.5180(6) 0.1075(5) 0.1252(4) 0.0670(15) Uani 1.000000
H3 H 0.4700(6) 0.0127(5) 0.0905(4) 0.0804(18) Uiso 1.000000
C4 C 0.1587(5) 0.1799(5) 0.1068(4) 0.0736(16) Uani 1.000000
H4a H 0.2354(6) 0.213(3) 0.1751(6) 0.110(2) Uiso 1.000000
H4b H 0.102(3) 0.228(3) 0.1104(18) 0.110(2) Uiso 1.000000
H4c H 0.097(3) 0.0828(6) 0.0898(14) 0.110(2) Uiso 1.000000
C3ba C 0.6661(6) 0.3850(5) 0.2286(4) 0.0654(14) Uani 1.000000
H3ba H 0.7174(6) 0.4796(5) 0.2640(4) 0.0785(17) Uiso 1.000000
C5ba C 0.7250(7) 0.3028(6) 0.2557(5) 0.0875(18) Uani 1.000000
H5ba H 0.8156(7) 0.3405(6) 0.3097(5) 0.105(2) Uiso 1.000000
C4ba C 0.6505(7) 0.1658(6) 0.2034(5) 0.0890(19) Uani 1.000000
H4ba H 0.6915(7) 0.1098(6) 0.2217(5) 0.107(2) Uiso 1.000000
O1 O 0.1905(3) 0.2384(3) -0.2338(2) 0.0514(8) Uani 1.000000
H1d H 0.2753(18) 0.307(3) -0.206(3) 0.0771(12) Uiso 1.000000
H1e H 0.191(4) 0.176(3) -0.280(3) 0.0771(12) Uiso 1.000000
C1 C 0.2850(5) -0.2066(5) 0.3998(4) 0.0671(15) Uani 1.000000
H1a H 0.2573(14) -0.276(2) 0.435(2) 0.101(2) Uiso 1.000000
H1b H 0.305(2) -0.241(3) 0.3381(5) 0.101(2) Uiso 1.000000
H1c H 0.3706(11) -0.1252(8) 0.449(2) 0.101(2) Uiso 1.000000


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C13 C26 1.361(6) .
C13 C17 1.379(6) .
C14 C20 1.379(6) .
C14 C17 1.385(6) .
C14 C9aa 1.444(6) .
C15 C30 1.366(6) .
C15 C16 1.379(6) .
C15 N1aa 1.418(6) .
C16 C2ba 1.366(6) .
C16 N2aa 1.392(5) .
C17 C1ba 1.484(6) .
C20 C29 1.361(6) .
C26 C29 1.361(7) .
C30 C37 1.399(7) .
C37 C38 1.386(7) .
C38 C2ba 1.383(7) .
O10 C18 1.384(5) .
N12 C9aa 1.358(5) .
N12 C0ba 1.374(5) .
N12 C18 1.473(5) .
C0aa C4aa 1.363(6) .
C0aa C0ba 1.387(6) .
C18 C1ba 1.505(6) .
C18 C1 1.507(6) .
N1aa C6aa 1.282(5) .
N2aa C6aa 1.343(5) .
N2aa C8aa 1.469(5) .
C9 C4aa 1.362(6) .
C9 C3aa 1.363(6) .
C11 N5aa 1.371(5) .
C11 C3aa 1.383(6) .
C11 C0ba 1.387(5) .
N5aa C9aa 1.313(5) .
C1aa C3ba 1.381(6) .
C1aa C7aa 1.414(6) .
C1aa C6aa 1.451(6) .
C7aa C3 1.363(6) .
C7aa C6 1.473(6) .
C8aa O2 1.369(5) .
C8aa C4 1.516(6) .
C8aa C6 1.531(6) .
C3 C4ba 1.353(7) .
C3ba C5ba 1.357(6) .
C5ba C4ba 1.348(7) .

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
C26 C13 C17 121.5(5) . .
C20 C14 C17 119.7(4) . .
C9aa C14 C17 118.1(4) . .
C9aa C14 C20 122.2(4) . .
C30 C15 C16 122.8(5) . .
N1aa C15 C16 109.3(4) . .
N1aa C15 C30 127.9(5) . .
N2aa C16 C15 105.6(4) . .
C2ba C16 C15 121.5(5) . .
C2ba C16 N2aa 133.0(5) . .
C14 C17 C13 118.3(4) . .
C1ba C17 C13 122.6(4) . .
C1ba C17 C14 119.0(4) . .
C29 C20 C14 120.4(4) . .
C29 C26 C13 119.7(5) . .
C26 C29 C20 120.3(5) . .
C37 C30 C15 116.3(5) . .
C38 C37 C30 120.6(6) . .
C2ba C38 C37 122.0(6) . .
C0ba N12 C18 128.4(3) . .
C9aa N12 C18 124.4(4) . .
C9aa N12 C0ba 106.4(3) . .
C0ba C0aa C4aa 116.6(4) . .
N12 C18 O10 109.1(4) . .
C1ba C18 O10 112.1(4) . .
C1ba C18 N12 106.8(3) . .
C1 C18 O10 107.1(3) . .
C1 C18 N12 109.0(4) . .
C1 C18 C1ba 112.6(4) . .
C6aa N1aa C15 103.9(4) . .
C6aa N2aa C16 105.7(4) . .
C8aa N2aa C16 127.3(4) . .
C8aa N2aa C6aa 124.9(4) . .
C4aa C9 C3aa 122.1(5) . .
N5aa C11 C3aa 130.0(4) . .
C0ba C11 C3aa 120.0(4) . .
C0ba C11 N5aa 109.9(4) . .
C11 C3aa C9 117.5(4) . .
C9 C4aa C0aa 122.0(5) . .
C9aa N5aa C11 105.2(3) . .
C6aa C1aa C7aa 118.6(4) . .
C3ba C1aa C7aa 118.9(4) . .
C3ba C1aa C6aa 122.4(4) . .
C6 C7aa C1aa 118.5(4) . .
C3 C7aa C1aa 118.1(5) . .
C3 C7aa C6 123.2(4) . .
N2aa C6aa N1aa 115.5(4) . .
C1aa C6aa N1aa 125.4(4) . .
C1aa C6aa N2aa 119.0(4) . .
C6 C8aa N2aa 105.8(4) . .
O2 C8aa N2aa 111.0(4) . .
O2 C8aa C6 111.0(4) . .
C4 C8aa N2aa 108.7(4) . .
C4 C8aa C6 113.2(4) . .
C4 C8aa O2 107.1(4) . .
C0aa C0ba N12 132.6(4) . .
C11 C0ba N12 105.6(4) . .
C11 C0ba C0aa 121.7(4) . .
N12 C9aa C14 120.0(4) . .
N5aa C9aa C14 127.2(4) . .
N5aa C9aa N12 112.8(4) . .
C18 C1ba C17 115.4(4) . .
C8aa C6 C7aa 114.9(4) . .
C38 C2ba C16 116.8(5) . .
C4ba C3 C7aa 120.9(5) . .
C5ba C3ba C1aa 121.0(5) . .
C4ba C5ba C3ba 119.2(6) . .
C5ba C4ba C3 121.9(5) . .

loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
C1aa C6aa 0.0010 0.0691 -0.0009


####################################################################### 
# 
# 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_exp_4270
_audit_block_doi                 10.5517/ccdc.csd.cc1pn6p7
_database_code_depnum_ccdc_archive 'CCDC 1568559'
_audit_update_record             
;
2017-08-12 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_cell_formula_units_Z            4
_cell_measurement_temperature    294.29(18)
_diffrn_ambient_temperature      294.29(18)
_exptl_crystal_description       block
_diffrn_measurement_device_type  agilent
_cell_measurement_reflns_used    2555
_cell_measurement_theta_min      3.3610
_cell_measurement_theta_max      26.7470
_cell_angle_alpha                105.175(5)
_cell_angle_beta                 101.292(5)
_cell_angle_gamma                114.625(8)
_cell_length_a                   11.1136(8)
_cell_length_b                   11.2993(9)
_cell_length_c                   12.7113(6)
_cell_volume                     1313.2(2)
_chemical_formula_moiety         'C16 H16 N2 O'
_chemical_formula_sum            'C16 H16 N2 O'
_chemical_formula_weight         252.32
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9983
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10915
_diffrn_reflns_theta_full        24.9971
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_F_000             536.2207
_exptl_crystal_density_diffrn    1.2761

_refine_diff_density_max         0.5901
_refine_diff_density_min         -0.4094
_refine_diff_density_rms         0.0535
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0554
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             6.3148
_refine_ls_goodness_of_fit_ref   1.0647
_refine_ls_matrix_type           full
_refine_ls_number_constraints    56
_refine_ls_number_parameters     351
_refine_ls_number_reflns         4631
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0646
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1550
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0685P)²+0.3388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3348
_reflns_number_total             4631
_reflns_threshold_expression     I>=2u(I)
_space_group_IT_number           2
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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
N4 N 0.2717(2) 0.6290(2) 0.59384(15) 0.0476(5) Uani 1.000000
C5 C 0.2438(2) 0.5113(2) 0.51321(17) 0.0432(5) Uani 1.000000
N6 N 0.1531(2) 0.4832(2) 0.40987(15) 0.0494(5) Uani 1.000000
H6 H 0.1209(2) 0.4110(2) 0.34672(15) 0.0593(6) Uiso 1.000000
C10 C 0.0709(2) 0.2501(2) 0.92248(17) 0.0476(6) Uani 1.000000
C11 C 0.1968(2) 0.6808(2) 0.53938(18) 0.0449(5) Uani 1.000000
C13 C 0.2010(3) 0.3594(2) 0.93759(17) 0.0464(6) Uani 1.000000
C14 C 0.1092(3) 0.8301(3) 0.5056(2) 0.0622(7) Uani 1.000000
H14 H 0.1045(3) 0.9124(3) 0.5317(2) 0.0747(8) Uiso 1.000000
C15 C 0.2957(2) 0.4152(2) 0.52778(17) 0.0445(5) Uani 1.000000
C16 C 0.1222(2) 0.5898(2) 0.42382(18) 0.0474(6) Uani 1.000000
C17 C 0.1908(3) 0.8041(3) 0.5809(2) 0.0558(6) Uani 1.000000
H17 H 0.2409(3) 0.8670(3) 0.6578(2) 0.0669(8) Uiso 1.000000
C18 C 0.4284(2) 0.4605(2) 0.60526(18) 0.0466(6) Uani 1.000000
C19 C 0.2087(3) 0.2724(3) 0.4593(2) 0.0536(6) Uani 1.000000
H19 H 0.1208(3) 0.2424(3) 0.4067(2) 0.0643(7) Uiso 1.000000
C21 C 0.0315(3) 0.1147(3) 0.84792(19) 0.0598(7) Uani 1.000000
H21 H -0.0547(3) 0.0397(3) 0.83685(19) 0.0717(8) Uiso 1.000000
C23 C 0.0331(3) 0.7367(3) 0.3910(2) 0.0689(8) Uani 1.000000
H23 H -0.0224(3) 0.7573(3) 0.3421(2) 0.0826(9) Uiso 1.000000
C24 C 0.2844(3) 0.3313(3) 0.8774(2) 0.0589(7) Uani 1.000000
H24 H 0.3705(3) 0.4052(3) 0.8865(2) 0.0706(8) Uiso 1.000000
C26 C 0.1152(3) 0.0891(3) 0.7909(2) 0.0673(8) Uani 1.000000
H26 H 0.0856(3) -0.0025(3) 0.7420(2) 0.0807(9) Uiso 1.000000
C28 C 0.2482(3) 0.1747(3) 0.4670(2) 0.0648(7) Uani 1.000000
H28 H 0.1885(3) 0.0798(3) 0.4197(2) 0.0778(9) Uiso 1.000000
C29 C 0.4647(3) 0.3583(3) 0.6118(2) 0.0600(7) Uani 1.000000
H29 H 0.5524(3) 0.3864(3) 0.6636(2) 0.0720(8) Uiso 1.000000
C34 C 0.3766(3) 0.2181(3) 0.5451(2) 0.0681(8) Uani 1.000000
H34 H 0.4038(3) 0.1525(3) 0.5528(2) 0.0817(9) Uiso 1.000000
C35 C 0.2419(3) 0.1964(3) 0.8047(2) 0.0672(8) Uani 1.000000
H35 H 0.2989(3) 0.1787(3) 0.7656(2) 0.0806(9) Uiso 1.000000
C37 C 0.0378(3) 0.6158(3) 0.3484(2) 0.0650(7) Uani 1.000000
H37 H -0.0138(3) 0.5530(3) 0.2716(2) 0.0781(9) Uiso 1.000000
O2 O 0.41237(18) 0.6572(2) 0.80869(13) 0.0620(5) Uani 1.000000
H2 H 0.3697(16) 0.655(3) 0.7473(10) 0.0930(7) Uiso 1.000000
C0aa C 0.5358(2) 0.6113(2) 0.67906(18) 0.0504(6) Uani 1.000000
H0aa H 0.6283(2) 0.6253(2) 0.67977(18) 0.0605(7) Uiso 1.000000
H0ab H 0.5164(2) 0.6706(2) 0.64352(18) 0.0605(7) Uiso 1.000000
C6 C 0.5404(3) 0.6594(3) 0.80348(19) 0.0548(6) Uani 1.000000
H6a H 0.5502(3) 0.5927(3) 0.83574(19) 0.0657(8) Uiso 1.000000
C1aa C 0.6641(3) 0.8024(3) 0.8771(2) 0.0733(8) Uani 1.000000
H1aa H 0.6620(12) 0.8684(5) 0.8431(10) 0.1100(12) Uiso 1.000000
H1ab H 0.6599(12) 0.8317(10) 0.9537(6) 0.1100(12) Uiso 1.000000
H1ac H 0.7498(3) 0.7991(6) 0.8818(15) 0.1100(12) Uiso 1.000000
O1 O 0.10458(18) 0.33063(19) 1.18037(13) 0.0591(5) Uani 1.000000
H1 H 0.1432(17) 0.4002(14) 1.1650(12) 0.0886(7) Uiso 1.000000
C2aa C -0.0252(3) 0.2275(3) 1.0868(2) 0.0698(8) Uani 1.000000
H2aa H -0.0254(3) 0.1376(3) 1.0662(2) 0.0837(9) Uiso 1.000000
C3 C -0.0302(3) 0.2661(3) 0.97937(19) 0.0558(6) Uani 1.000000
H3a H -0.0101(3) 0.3632(3) 1.00215(19) 0.0669(8) Uiso 1.000000
H3b H -0.1252(3) 0.2069(3) 0.92286(19) 0.0669(8) Uiso 1.000000
C3aa C -0.1453(3) 0.2081(4) 1.1242(3) 0.0951(11) Uani 1.000000
H3aa H -0.1311(13) 0.192(3) 1.1950(12) 0.1427(16) Uiso 1.000000
H3ab H -0.1545(16) 0.2911(11) 1.137(2) 0.1427(16) Uiso 1.000000
H3ac H -0.2297(5) 0.1283(16) 1.0651(10) 0.1427(16) Uiso 1.000000
N2a N 0.3355(2) 0.6160(2) 0.99034(18) 0.0518(5) Uani 1.000000
N1 N 0.2435(2) 0.5464(2) 1.11738(15) 0.0504(5) Uani 1.000000
C2 C 0.2571(2) 0.5058(2) 1.01557(18) 0.0466(6) Uani 1.000000
C4aa C 0.3758(2) 0.7363(2) 1.0818(2) 0.0518(6) Uani 1.000000
C4 C 0.3176(2) 0.6925(2) 1.16112(19) 0.0501(6) Uani 1.000000
C6aa C 0.4545(3) 0.8781(3) 1.1026(3) 0.0681(8) Uani 1.000000
H6aa H 0.4938(3) 0.9071(3) 1.0495(3) 0.0817(9) Uiso 1.000000
C5aa C 0.3370(3) 0.7910(3) 1.2642(2) 0.0660(7) Uani 1.000000
H5aa H 0.2987(3) 0.7636(3) 1.3183(2) 0.0792(9) Uiso 1.000000
C7 C 0.4150(3) 0.9303(3) 1.2828(3) 0.0798(9) Uani 1.000000
H7 H 0.4300(3) 0.9986(3) 1.3512(3) 0.0958(11) Uiso 1.000000
C8 C 0.4720(3) 0.9727(3) 1.2035(3) 0.0798(9) Uani 1.000000
H8 H 0.5238(3) 1.0686(3) 1.2196(3) 0.0957(11) Uiso 1.000000
H2a H 0.358(3) 0.618(3) 0.923(2) 0.073(8) Uiso 1.000000


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N4 C5 1.317(3) .
N4 C11 1.381(3) .
C5 N6 1.356(3) .
C5 C15 1.459(3) .
N6 C16 1.363(3) .
C10 C13 1.390(3) .
C10 C21 1.396(3) .
C10 C3 1.496(3) .
C11 C16 1.387(3) .
C11 C17 1.390(3) .
C13 C24 1.394(3) .
C13 C2 1.466(3) .
C14 C17 1.361(4) .
C14 C23 1.386(4) .
C15 C19 1.390(3) .
C15 C18 1.395(3) .
C16 C37 1.382(3) .
C18 C29 1.389(3) .
C18 C0aa 1.496(3) .
C19 C28 1.365(4) .
C21 C26 1.362(4) .
C23 C37 1.358(4) .
C24 C35 1.376(4) .
C26 C35 1.361(4) .
C28 C34 1.368(4) .
C29 C34 1.366(4) .
O2 C6 1.428(3) .
C0aa C6 1.515(3) .
C6 C1aa 1.493(4) .
O1 C2aa 1.434(3) .
C2aa C3aa 1.454(4) .
C2aa C3 1.537(3) .
N2a C2 1.352(3) .
N2a C4aa 1.364(3) .
N1 C2 1.316(3) .
N1 C4 1.385(3) .
C4aa C6aa 1.386(3) .
C4aa C4 1.390(3) .
C4 C5aa 1.389(3) .
C6aa C8 1.356(4) .
C5aa C7 1.368(4) .
C7 C8 1.378(5) .

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
C11 N4 C5 105.64(17) . .
N6 C5 N4 111.5(2) . .
C15 C5 N4 126.95(19) . .
C15 C5 N6 121.47(19) . .
C16 N6 C5 107.88(18) . .
C21 C10 C13 117.3(2) . .
C3 C10 C13 125.2(2) . .
C3 C10 C21 117.5(2) . .
C16 C11 N4 109.4(2) . .
C17 C11 N4 130.8(2) . .
C17 C11 C16 119.7(2) . .
C24 C13 C10 119.8(2) . .
C2 C13 C10 123.0(2) . .
C2 C13 C24 117.2(2) . .
C23 C14 C17 121.6(3) . .
C18 C15 C5 123.1(2) . .
C19 C15 C5 117.8(2) . .
C19 C15 C18 119.0(2) . .
C11 C16 N6 105.5(2) . .
C37 C16 N6 132.6(2) . .
C37 C16 C11 121.9(2) . .
C14 C17 C11 118.0(2) . .
C29 C18 C15 117.5(2) . .
C0aa C18 C15 124.7(2) . .
C0aa C18 C29 117.7(2) . .
C28 C19 C15 122.0(2) . .
C26 C21 C10 122.1(3) . .
C37 C23 C14 121.4(3) . .
C35 C24 C13 121.2(3) . .
C35 C26 C21 120.6(2) . .
C34 C28 C19 119.2(3) . .
C34 C29 C18 122.5(2) . .
C29 C34 C28 119.7(3) . .
C26 C35 C24 119.0(3) . .
C23 C37 C16 117.4(2) . .
C6 C0aa C18 114.66(19) . .
C0aa C6 O2 111.21(18) . .
C1aa C6 O2 110.3(2) . .
C1aa C6 C0aa 111.9(2) . .
C3 C2aa O1 109.9(2) . .
C3aa C2aa O1 110.7(2) . .
C3aa C2aa C3 114.2(3) . .
C2aa C3 C10 114.4(2) . .
C4aa N2a C2 107.3(2) . .
C4 N1 C2 105.27(19) . .
N1 C2 C13 125.7(2) . .
C6aa C4aa C4 121.6(2) . .
C4aa C4 N1 109.1(2) . .
C5aa C4 N1 130.5(2) . .
C5aa C4 C4aa 120.3(2) . .
C8 C6aa C4aa 117.3(3) . .
C7 C5aa C4 117.0(3) . .
C8 C7 C5aa 122.2(3) . .
C7 C8 C6aa 121.6(3) . .

loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
C2aa C3aa 0.0010 0.0639 -0.0024


####################################################################### 
# 
# 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_exp_3629
_audit_block_doi                 10.5517/ccdc.csd.cc1p4k7m
_database_code_depnum_ccdc_archive 'CCDC 1553510'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_cell_formula_units_Z            4
_cell_angle_alpha                90
_cell_angle_beta                 99.316(18)
_cell_angle_gamma                90
_cell_length_a                   7.1819(13)
_cell_length_b                   12.909(3)
_cell_length_c                   16.108(3)
_cell_volume                     1473.7(5)
_cell_measurement_temperature    294.29(18)
_cell_measurement_reflns_used    1538
_cell_measurement_theta_min      3.3270
_cell_measurement_theta_max      24.3560
_chemical_formula_moiety         'C17 H14 N2 O2 S'
_chemical_formula_sum            'C17 H14 N2 O2 S'
_chemical_formula_weight         310.38
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1015
_diffrn_reflns_av_unetI/netI     0.1315
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11613
_diffrn_reflns_theta_full        24.9999
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.87
_diffrn_ambient_temperature      294.29(18)
_diffrn_measurement_device_type  agilent
_exptl_crystal_description       block
_exptl_absorpt_coefficient_mu    0.228
_exptl_crystal_F_000             648.7721
_exptl_crystal_density_diffrn    1.3988

_refine_diff_density_max         0.4096
_refine_diff_density_min         -0.4828
_refine_diff_density_rms         0.1174
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0643
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.0872
_refine_ls_goodness_of_fit_ref   1.0019
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0019
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1486
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                1572
_reflns_number_total             2600
_reflns_threshold_expression     I>=2u(I)
_space_group_IT_number           14
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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
S1 S -0.00128(14) 0.32242(9) 0.22445(5) 0.0530(4) Uani 1.000000
N2 N -0.2272(4) 0.4323(2) -0.00481(15) 0.0352(7) Uani 1.000000
N4 N -0.1633(4) 0.5280(2) 0.11557(16) 0.0413(8) Uani 1.000000
C6 C -0.1556(4) 0.4363(3) 0.08185(19) 0.0368(9) Uani 1.000000
C10 C -0.0900(4) 0.3411(3) 0.11976(19) 0.0380(9) Uani 1.000000
C11 C -0.0940(4) 0.2497(3) 0.0737(2) 0.0357(8) Uani 1.000000
C13 C -0.0247(5) 0.1648(3) 0.1259(2) 0.0488(10) Uani 1.000000
H13 H -0.0168(5) 0.0975(3) 0.1062(2) 0.0586(12) Uiso 1.000000
C14 C -0.2433(5) 0.5905(3) 0.0492(2) 0.0397(9) Uani 1.000000
C15 C -0.2855(4) 0.5342(3) -0.0268(2) 0.0378(9) Uani 1.000000
C16 C 0.0284(5) 0.1924(3) 0.2068(2) 0.0536(11) Uani 1.000000
H16 H 0.0763(5) 0.1459(3) 0.2490(2) 0.0644(13) Uiso 1.000000
C17 C -0.2823(5) 0.6958(3) 0.0502(2) 0.0509(10) Uani 1.000000
H17 H -0.2520(5) 0.7338(3) 0.0996(2) 0.0610(12) Uiso 1.000000
C18 C -0.3702(5) 0.5816(3) -0.1003(2) 0.0471(10) Uani 1.000000
H18 H -0.3994(5) 0.5445(3) -0.1502(2) 0.0565(12) Uiso 1.000000
C19 C -0.3662(5) 0.7432(3) -0.0227(3) 0.0574(11) Uani 1.000000
H19 H -0.3941(5) 0.8135(3) -0.0227(3) 0.0689(13) Uiso 1.000000
C21 C -0.4097(5) 0.6856(3) -0.0971(3) 0.0562(11) Uani 1.000000
H21 H -0.4671(5) 0.7188(3) -0.1458(3) 0.0675(13) Uiso 1.000000
O2 O -0.0384(4) 0.0988(2) -0.06522(17) 0.0647(8) Uani 1.000000
C3 C -0.2339(4) 0.3416(3) -0.05292(19) 0.0348(9) Uani 1.000000
O4 O -0.3482(4) 0.1252(2) -0.09386(17) 0.0669(9) Uani 1.000000
C5 C -0.1695(4) 0.2522(3) -0.0141(2) 0.0375(9) Uani 1.000000
C1 C -0.1724(5) 0.1515(3) -0.0608(2) 0.0458(10) Uani 1.000000
C7 C -0.3067(5) 0.3519(3) -0.1448(2) 0.0508(10) Uani 1.000000
H7a H -0.4368(11) 0.3724(18) -0.1527(2) 0.0761(16) Uiso 1.000000
H7b H -0.234(2) 0.4032(13) -0.1687(4) 0.0761(16) Uiso 1.000000
H7c H -0.296(3) 0.2865(5) -0.1721(3) 0.0761(16) Uiso 1.000000
C2 C -0.5714(6) -0.0024(4) -0.1448(3) 0.0836(15) Uani 1.000000
H2a H -0.6456(7) 0.0483(12) -0.1791(16) 0.125(2) Uiso 1.000000
H2b H -0.5918(9) -0.0694(10) -0.1706(17) 0.125(2) Uiso 1.000000
H2c H -0.6078(12) -0.004(2) -0.0901(3) 0.125(2) Uiso 1.000000
C4 C -0.3710(6) 0.0248(4) -0.1368(3) 0.0759(14) Uani 1.000000
H4a H -0.3334(6) 0.0296(4) -0.1919(3) 0.0911(17) Uiso 1.000000
H4b H -0.2938(6) -0.0273(4) -0.1043(3) 0.0911(17) Uiso 1.000000


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C10 1.721(3) .
S1 C16 1.721(4) .
N2 C3 1.401(4) .
N2 C15 1.408(4) .
N2 C6 1.408(4) .
N4 C6 1.308(4) .
N4 C14 1.388(4) .
C6 C10 1.418(5) .
C10 C11 1.393(5) .
C11 C13 1.421(5) .
C11 C5 1.430(4) .
C13 C16 1.346(5) .
C14 C17 1.388(5) .
C14 C15 1.415(4) .
C15 C18 1.383(4) .
C17 C19 1.373(5) .
C18 C21 1.375(5) .
C19 C21 1.401(5) .
O2 C1 1.190(4) .
C3 C5 1.358(5) .
C3 C7 1.494(4) .
O4 C1 1.333(4) .
O4 C4 1.465(4) .
C5 C1 1.500(5) .
C2 C4 1.467(5) .

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
C16 S1 C10 90.64(17) . .
C15 N2 C6 105.2(3) . .
C3 N2 C6 123.6(3) . .
C3 N2 C15 131.3(3) . .
C14 N4 C6 104.3(3) . .
N4 C6 N2 114.3(3) . .
C10 C6 N2 116.0(3) . .
C10 C6 N4 129.7(3) . .
C6 C10 S1 126.0(3) . .
C11 C10 S1 112.1(3) . .
C11 C10 C6 121.9(3) . .
C13 C11 C10 111.3(3) . .
C5 C11 C10 118.7(3) . .
C5 C11 C13 130.0(3) . .
C16 C13 C11 112.7(4) . .
C15 C14 N4 111.8(3) . .
C17 C14 N4 128.3(3) . .
C17 C14 C15 119.8(3) . .
C14 C15 N2 104.4(3) . .
C18 C15 N2 134.5(3) . .
C18 C15 C14 121.1(3) . .
C13 C16 S1 113.2(3) . .
C19 C17 C14 119.2(4) . .
C21 C18 C15 117.7(3) . .
C21 C19 C17 120.1(4) . .
C19 C21 C18 122.1(4) . .
C5 C3 N2 118.5(3) . .
C7 C3 N2 116.7(3) . .
C7 C3 C5 124.8(3) . .
C4 O4 C1 116.2(3) . .
C3 C5 C11 121.4(3) . .
C1 C5 C11 116.6(3) . .
C1 C5 C3 122.0(3) . .
O4 C1 O2 123.6(4) . .
C5 C1 O2 125.4(3) . .
C5 C1 O4 110.9(3) . .
C2 C4 O4 106.6(3) . .


####################################################################### 
# 
# 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_exp_5146
_audit_block_doi                 10.5517/ccdc.csd.cc1zr170
_database_code_depnum_ccdc_archive 'CCDC 1839392'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C21 H22 N2 O3'
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_weight         350.42
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y,-z
3 -x,-y,-z
4 x-1/2,-y,z
5 x+1/2,y+1/2,z+1/2
6 -x+1,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z+1/2
8 x,-y+1/2,z+1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   13.1564(5)
_cell_length_b                   14.1743(6)
_cell_length_c                   20.5373(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.892(5)
_cell_angle_gamma                90
_cell_volume                     3821.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2696
_cell_measurement_temperature    295.92(10)
_cell_measurement_theta_max      29.3140
_cell_measurement_theta_min      4.3950
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2182
_exptl_crystal_F_000             1488.7215
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0357
_exptl_crystal_description       block
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10338
_diffrn_reflns_theta_full        24.9934
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.45
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.92(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9967
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0274183000
_diffrn_orient_matrix_UB_12      -0.0001583000
_diffrn_orient_matrix_UB_13      -0.0285660000
_diffrn_orient_matrix_UB_21      0.0465775000
_diffrn_orient_matrix_UB_22      0.0008039000
_diffrn_orient_matrix_UB_23      0.0195203000
_diffrn_orient_matrix_UB_31      0.0006937000
_diffrn_orient_matrix_UB_32      -0.0500420000
_diffrn_orient_matrix_UB_33      0.0004098000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -24
_reflns_number_gt                2619
_reflns_number_total             3352
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.2134
_refine_diff_density_min         -0.2835
_refine_diff_density_rms         0.0682
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             5.9131
_refine_ls_goodness_of_fit_ref   1.0675
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.0675
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1528
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C20(H20), C16(H16), C8(H8), C15(H15), C21(H21), C22(H22), C18(H18)
2.c Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C11(H11a,H11b,H11c), C1a(H1aa,H1ab,H1ac), C1b(H1ba,H1bb,
 H1bc)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.53779(9) 0.72442(7) 0.28812(7) 0.0412(4) Uani 1.000000 .
N2 N 0.51178(10) 0.88081(9) 0.26039(6) 0.0312(3) Uani 1.000000 .
C4 C 0.59057(13) 0.89365(11) 0.21940(8) 0.0329(4) Uani 1.000000 .
C6 C 0.34778(13) 0.89963(11) 0.34147(8) 0.0343(4) Uani 1.000000 .
C7 C 0.40359(12) 0.80689(11) 0.33855(8) 0.0331(4) Uani 1.000000 .
C8 C 0.66221(13) 0.83349(12) 0.19536(9) 0.0405(5) Uani 1.000000 .
N9 N 0.51452(11) 1.03565(10) 0.23777(7) 0.0417(4) Uani 1.000000 .
C10 C 0.38265(13) 0.97825(11) 0.30890(8) 0.0353(4) Uani 1.000000 .
C12 C 0.46076(12) 0.79181(10) 0.27636(8) 0.0316(4) Uani 1.000000 .
C13 C 0.46917(12) 0.96787(11) 0.26904(8) 0.0333(4) Uani 1.000000 .
C14 C 0.66277(16) 1.02803(14) 0.16661(10) 0.0524(5) Uani 1.000000 .
C15 C 0.26504(14) 0.90945(14) 0.37904(10) 0.0473(5) Uani 1.000000 .
C16 C 0.73340(15) 0.87254(13) 0.15723(9) 0.0475(5) Uani 1.000000 .
C17 C 0.59086(13) 0.99041(12) 0.20615(9) 0.0378(4) Uani 1.000000 .
C18 C 0.33365(15) 1.06427(12) 0.31459(9) 0.0475(5) Uani 1.000000 .
C19 C 0.38733(14) 0.76452(13) 0.21958(9) 0.0453(5) Uani 1.000000 .
C20 C 0.73321(16) 0.96833(14) 0.14294(10) 0.0540(6) Uani 1.000000 .
C21 C 0.21727(15) 0.99576(14) 0.38465(10) 0.0547(6) Uani 1.000000 .
C22 C 0.25230(16) 1.07273(14) 0.35243(10) 0.0546(6) Uani 1.000000 .
O2 O 0.44190(10) 0.73394(9) 0.43916(6) 0.0498(4) Uani 1.000000 .
C3 C 0.47569(13) 0.79895(12) 0.39949(8) 0.0385(4) Uani 1.000000 .
O3 O 0.54926(11) 0.84701(12) 0.40993(7) 0.0667(5) Uani 1.000000 .
C5 C 0.4976(2) 0.71149(18) 0.50214(10) 0.0687(7) Uani 1.000000 .
C11 C 0.5051(3) 0.7987(2) 0.54463(12) 0.0930(9) Uani 1.000000 .
C1a C 0.4306(3) 0.6388(2) 0.53069(15) 0.1200(12) Uani 1.000000 .
C1b C 0.6002(3) 0.6705(3) 0.48876(16) 0.1371(17) Uani 1.000000 .
H14 H 0.66286(16) 1.09201(14) 0.15658(10) 0.0629(7) Uiso 1.000000 R
H20 H 0.78200(16) 0.99240(14) 0.11673(10) 0.0648(7) Uiso 1.000000 R
H16 H 0.78267(15) 0.83394(13) 0.14069(9) 0.0569(6) Uiso 1.000000 R
H8 H 0.66218(13) 0.76927(12) 0.20463(9) 0.0486(5) Uiso 1.000000 R
H15 H 0.24117(14) 0.85728(14) 0.40084(10) 0.0568(6) Uiso 1.000000 R
H21 H 0.16177(15) 1.00156(14) 0.41010(10) 0.0656(7) Uiso 1.000000 R
H22 H 0.22067(16) 1.13095(14) 0.35630(10) 0.0656(7) Uiso 1.000000 R
H18 H 0.35626(15) 1.11670(12) 0.29249(9) 0.0570(6) Uiso 1.000000 R
H1 H 0.5157(5) 0.6720(2) 0.2779(9) 0.0618(5) Uiso 1.000000 GR
H7 H 0.35300(12) 0.75637(11) 0.34038(8) 0.0398(5) Uiso 1.000000 R
H19a H 0.4232(2) 0.7610(8) 0.18048(14) 0.0680(7) Uiso 1.000000 GR
H19b H 0.3578(7) 0.7042(4) 0.2281(3) 0.0680(7) Uiso 1.000000 GR
H19c H 0.3344(5) 0.8111(4) 0.2142(4) 0.0680(7) Uiso 1.000000 GR
H11a H 0.5479(13) 0.8445(6) 0.5255(5) 0.1395(14) Uiso 1.000000 GR
H11b H 0.4384(3) 0.8249(9) 0.5480(8) 0.1395(14) Uiso 1.000000 GR
H11c H 0.5338(15) 0.7822(3) 0.5873(3) 0.1395(14) Uiso 1.000000 GR
H1aa H 0.3655(8) 0.6662(6) 0.5376(13) 0.1800(19) Uiso 1.000000 GR
H1ab H 0.4217(17) 0.5865(9) 0.5011(6) 0.1800(19) Uiso 1.000000 GR
H1ac H 0.4619(11) 0.6172(15) 0.5716(7) 0.1800(19) Uiso 1.000000 GR
H1ba H 0.5918(4) 0.6250(16) 0.4542(11) 0.206(2) Uiso 1.000000 GR
H1bb H 0.6445(8) 0.7201(4) 0.4761(15) 0.206(2) Uiso 1.000000 GR
H1bc H 0.6295(11) 0.640(2) 0.5275(5) 0.206(2) Uiso 1.000000 GR


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 C12 1.4016(19) . ?
N2 C4 1.391(2) . ?
N2 C12 1.476(2) . ?
N2 C13 1.372(2) . ?
C4 C8 1.386(2) . ?
C4 C17 1.398(2) . ?
C6 C7 1.509(2) . ?
C6 C10 1.393(2) . ?
C6 C15 1.383(2) . ?
C7 C12 1.541(2) . ?
C7 C3 1.522(2) . ?
C8 C16 1.377(2) . ?
N9 C13 1.320(2) . ?
N9 C17 1.389(2) . ?
C10 C13 1.454(2) . ?
C10 C18 1.388(2) . ?
C12 C19 1.513(2) . ?
C14 C17 1.394(2) . ?
C14 C20 1.368(3) . ?
C15 C21 1.384(3) . ?
C16 C20 1.389(3) . ?
C18 C22 1.370(2) . ?
C21 C22 1.372(3) . ?
O2 C3 1.327(2) . ?
O2 C5 1.477(2) . ?
C3 O3 1.191(2) . ?
C5 C11 1.513(4) . ?
C5 C1a 1.501(4) . ?
C5 C1b 1.512(4) . ?

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
C12 N2 C4 127.95(13) . . ?
C13 N2 C4 106.77(13) . . ?
C13 N2 C12 122.95(13) . . ?
C8 C4 N2 133.44(15) . . ?
C17 C4 N2 104.96(13) . . ?
C17 C4 C8 121.53(15) . . ?
C10 C6 C7 120.05(15) . . ?
C15 C6 C7 120.88(15) . . ?
C15 C6 C10 118.98(16) . . ?
C12 C7 C6 114.84(13) . . ?
C3 C7 C6 108.03(13) . . ?
C3 C7 C12 111.06(13) . . ?
C16 C8 C4 117.41(16) . . ?
C17 N9 C13 104.85(13) . . ?
C13 C10 C6 119.03(15) . . ?
C18 C10 C6 119.49(16) . . ?
C18 C10 C13 121.47(15) . . ?
N2 C12 O1 106.64(12) . . ?
C7 C12 O1 109.85(13) . . ?
C7 C12 N2 108.70(12) . . ?
C19 C12 O1 112.02(13) . . ?
C19 C12 N2 108.87(13) . . ?
C19 C12 C7 110.63(14) . . ?
N9 C13 N2 112.92(14) . . ?
C10 C13 N2 120.41(14) . . ?
C10 C13 N9 126.67(14) . . ?
C20 C14 C17 118.24(18) . . ?
C21 C15 C6 120.96(18) . . ?
C20 C16 C8 121.43(17) . . ?
N9 C17 C4 110.50(14) . . ?
C14 C17 C4 119.97(16) . . ?
C14 C17 N9 129.53(16) . . ?
C22 C18 C10 120.65(17) . . ?
C16 C20 C14 121.39(17) . . ?
C22 C21 C15 119.58(18) . . ?
C21 C22 C18 120.34(18) . . ?
C5 O2 C3 121.37(16) . . ?
O2 C3 C7 109.88(14) . . ?
O3 C3 C7 124.00(16) . . ?
O3 C3 O2 126.07(17) . . ?
C11 C5 O2 109.8(2) . . ?
C1a C5 O2 102.8(2) . . ?
C1a C5 C11 110.7(2) . . ?
C1b C5 O2 108.63(19) . . ?
C1b C5 C11 113.2(3) . . ?
C1b C5 C1a 111.2(3) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.619
####################################################################### 
# 
# 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_exp_5369
_audit_block_doi                 10.5517/ccdc.csd.cc1zr2ph
_database_code_depnum_ccdc_archive 'CCDC 1839437'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_audit_creation_date             2018-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.37
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.0284(9)
_cell_length_b                   12.6694(8)
_cell_length_c                   14.2980(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.266(8)
_cell_angle_gamma                90
_cell_volume                     1625.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1405
_cell_measurement_theta_max      24.0260
_cell_measurement_theta_min      3.7950
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57980
_exptl_crystal_description       block
_diffrn_ambient_temperature      298
_cell_measurement_temperature    298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3170
_exptl_crystal_F_000             680.3401
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7884
_diffrn_reflns_theta_full        24.9988
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.52
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  79.00   1.00    7.50    --   15.49  57.00-120.00   76
  2  ω    -49.00  70.00   1.00    7.50    --   15.49   0.00-150.00  119
  3  ω    -16.00  16.00   1.00    7.50    --  -16.12 -99.00-120.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0622281000
_diffrn_orient_matrix_UB_12      0.0050183000
_diffrn_orient_matrix_UB_13      0.0260166000
_diffrn_orient_matrix_UB_21      0.0462003000
_diffrn_orient_matrix_UB_22      -0.0118659000
_diffrn_orient_matrix_UB_23      0.0419992000
_diffrn_orient_matrix_UB_31      0.0158225000
_diffrn_orient_matrix_UB_32      0.0544826000
_diffrn_orient_matrix_UB_33      0.0067300000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -7
_reflns_number_gt                1893
_reflns_number_total             2850
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2633
_refine_diff_density_min         -0.3260
_refine_diff_density_rms         0.0710
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.7860
_refine_ls_goodness_of_fit_ref   1.0654
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.0654
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.2104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1359
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00L(H00e,H00l)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00M(H00M), C00N(H00N), C00H(H00H), C00G(H00G), C00J(H00J),
 C00K(H00K), C00I(H00I)
2.d Idealised Me refined as rotating group:
 C00E(H00a,H00c,H00d), C00O(H00o,H00p,H00q)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O001 O 0.39363(18) 0.53867(11) 0.73764(12) 0.0432(5) Uani 1.000000 .
O002 O 0.49594(19) 0.30345(13) 0.69015(13) 0.0519(5) Uani 1.000000 .
O003 O 0.60725(19) 0.42929(13) 0.61263(12) 0.0511(5) Uani 1.000000 .
N004 N 0.2130(2) 0.40996(13) 0.73878(14) 0.0360(5) Uani 1.000000 .
N005 N 0.1047(2) 0.25698(14) 0.77030(15) 0.0443(6) Uani 1.000000 .
C006 C 0.4885(3) 0.37932(19) 0.64058(17) 0.0388(6) Uani 1.000000 .
C007 C 0.2776(3) 0.49077(16) 0.68040(17) 0.0360(6) Uani 1.000000 .
C008 C 0.1956(3) 0.41264(17) 0.83354(18) 0.0400(6) Uani 1.000000 .
C009 C 0.1549(3) 0.31602(16) 0.70462(18) 0.0388(6) Uani 1.000000 .
C00A C 0.2389(3) 0.35225(17) 0.55125(18) 0.0393(6) Uani 1.000000 .
C00B C 0.3444(3) 0.43197(17) 0.60039(17) 0.0385(6) Uani 1.000000 .
C00C C 0.1483(3) 0.29374(17) 0.60501(18) 0.0404(6) Uani 1.000000 .
C00D C 0.1301(3) 0.31600(17) 0.85221(19) 0.0424(6) Uani 1.000000 .
C00E C 0.1568(3) 0.56766(17) 0.6429(2) 0.0496(7) Uani 1.000000 .
C00F C 0.2263(3) 0.48786(19) 0.9030(2) 0.0508(7) Uani 1.000000 .
C00G C 0.2327(3) 0.3340(2) 0.45576(19) 0.0511(7) Uani 1.000000 .
C00H C 0.0979(3) 0.2929(2) 0.9428(2) 0.0566(8) Uani 1.000000 .
C00I C 0.0505(3) 0.21813(18) 0.5615(2) 0.0516(7) Uani 1.000000 .
C00J C 0.1362(3) 0.2581(2) 0.4136(2) 0.0604(8) Uani 1.000000 .
C00K C 0.0464(3) 0.2015(2) 0.4668(2) 0.0618(9) Uani 1.000000 .
C00L C 0.7524(3) 0.3971(2) 0.6580(2) 0.0641(9) Uani 1.000000 .
C00M C 0.1926(3) 0.4637(2) 0.9912(2) 0.0641(8) Uani 1.000000 .
C00N C 0.1301(3) 0.3664(2) 1.0117(2) 0.0664(9) Uani 1.000000 .
C00O C 0.7894(3) 0.4565(3) 0.7467(2) 0.0748(10) Uani 1.000000 .
H00F H 0.2683(3) 0.55253(19) 0.8901(2) 0.0609(9) Uiso 1.000000 R
H00M H 0.2116(3) 0.5132(2) 1.0390(2) 0.0769(10) Uiso 1.000000 R
H00N H 0.1104(3) 0.3518(2) 1.0729(2) 0.0797(10) Uiso 1.000000 R
H00H H 0.0553(3) 0.2285(2) 0.9562(2) 0.0680(9) Uiso 1.000000 R
H00G H 0.2932(3) 0.3725(2) 0.41958(19) 0.0613(9) Uiso 1.000000 R
H00J H 0.1325(3) 0.2456(2) 0.3493(2) 0.0725(10) Uiso 1.000000 R
H00K H -0.0182(3) 0.1512(2) 0.4380(2) 0.0742(10) Uiso 1.000000 R
H00I H -0.0111(3) 0.17952(18) 0.5968(2) 0.0619(9) Uiso 1.000000 R
H001 H 0.3892(18) 0.60283(19) 0.7303(14) 0.0648(7) Uiso 1.000000 GR
H00B H 0.3683(3) 0.48425(17) 0.55380(17) 0.0462(7) Uiso 1.000000 R
H00a H 0.1189(13) 0.6033(9) 0.6945(2) 0.0744(11) Uiso 1.000000 GR
H00c H 0.1976(5) 0.6185(8) 0.6030(9) 0.0744(11) Uiso 1.000000 GR
H00d H 0.0774(9) 0.5298(2) 0.6074(10) 0.0744(11) Uiso 1.000000 GR
H00e H 0.7514(3) 0.3221(2) 0.6713(2) 0.0770(10) Uiso 1.000000 R
H00l H 0.8278(3) 0.4101(2) 0.6159(2) 0.0770(10) Uiso 1.000000 R
H00o H 0.793(2) 0.5307(3) 0.7331(3) 0.1121(14) Uiso 1.000000 GR
H00p H 0.7148(13) 0.4434(13) 0.7882(6) 0.1121(14) Uiso 1.000000 GR
H00q H 0.8848(11) 0.4341(12) 0.7762(8) 0.1121(14) Uiso 1.000000 GR


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
O001 C007 1.396(2) . ?
O001 H001 0.8200 . ?
O002 C006 1.192(3) . ?
O003 C006 1.343(3) . ?
O003 C00L 1.455(3) . ?
N004 C007 1.480(3) . ?
N004 C008 1.381(3) . ?
N004 C009 1.369(3) . ?
N005 C009 1.319(3) . ?
N005 C00D 1.387(3) . ?
C006 C00B 1.518(3) . ?
C007 C00B 1.542(3) . ?
C007 C00E 1.516(3) . ?
C008 C00D 1.398(3) . ?
C008 C00F 1.383(3) . ?
C009 C00C 1.447(3) . ?
C00A C00B 1.508(3) . ?
C00A C00C 1.396(3) . ?
C00A C00G 1.380(3) . ?
C00B H00B 0.9800 . ?
C00C C00I 1.401(3) . ?
C00D C00H 1.389(4) . ?
C00E H00a 0.9600 . ?
C00E H00c 0.9600 . ?
C00E H00d 0.9600 . ?
C00F C00M 1.364(4) . ?
C00F H00F 0.9300 . ?
C00G C00J 1.390(4) . ?
C00G H00G 0.9300 . ?
C00H C00N 1.364(4) . ?
C00H H00H 0.9300 . ?
C00I C00K 1.367(4) . ?
C00I H00I 0.9300 . ?
C00J C00K 1.373(4) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L C00O 1.482(4) . ?
C00L H00e 0.9700 . ?
C00L H00l 0.9700 . ?
C00M C00N 1.400(4) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00o 0.9600 . ?
C00O H00p 0.9600 . ?
C00O H00q 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
H001 O001 C007 109.5 . . ?
C00L O003 C006 116.4(2) . . ?
C008 N004 C007 129.05(18) . . ?
C009 N004 C007 124.0(2) . . ?
C009 N004 C008 106.94(19) . . ?
C00D N005 C009 104.91(19) . . ?
O003 C006 O002 124.2(2) . . ?
C00B C006 O002 124.7(2) . . ?
C00B C006 O003 111.1(2) . . ?
N004 C007 O001 106.67(18) . . ?
C00B C007 O001 108.42(19) . . ?
C00B C007 N004 107.12(17) . . ?
C00E C007 O001 113.15(18) . . ?
C00E C007 N004 109.33(19) . . ?
C00E C007 C00B 111.8(2) . . ?
C00D C008 N004 105.2(2) . . ?
C00F C008 N004 133.3(2) . . ?
C00F C008 C00D 121.5(2) . . ?
N005 C009 N004 112.8(2) . . ?
C00C C009 N004 119.6(2) . . ?
C00C C009 N005 127.6(2) . . ?
C00C C00A C00B 118.5(2) . . ?
C00G C00A C00B 121.9(2) . . ?
C00G C00A C00C 119.6(2) . . ?
C007 C00B C006 108.64(19) . . ?
C00A C00B C006 110.70(18) . . ?
C00A C00B C007 113.0(2) . . ?
H00B C00B C006 108.11(14) . . ?
H00B C00B C007 108.11(11) . . ?
H00B C00B C00A 108.11(13) . . ?
C00A C00C C009 118.3(2) . . ?
C00I C00C C009 121.8(2) . . ?
C00I C00C C00A 119.8(2) . . ?
C008 C00D N005 110.2(2) . . ?
C00H C00D N005 129.9(2) . . ?
C00H C00D C008 119.9(2) . . ?
H00a C00E C007 109.5 . . ?
H00c C00E C007 109.5 . . ?
H00c C00E H00a 109.5 . . ?
H00d C00E C007 109.5 . . ?
H00d C00E H00a 109.5 . . ?
H00d C00E H00c 109.5 . . ?
C00M C00F C008 117.5(2) . . ?
H00F C00F C008 121.24(15) . . ?
H00F C00F C00M 121.24(16) . . ?
C00J C00G C00A 120.1(3) . . ?
H00G C00G C00A 119.97(16) . . ?
H00G C00G C00J 119.97(19) . . ?
C00N C00H C00D 118.7(3) . . ?
H00H C00H C00D 120.67(16) . . ?
H00H C00H C00N 120.67(18) . . ?
C00K C00I C00C 119.5(3) . . ?
H00I C00I C00C 120.23(17) . . ?
H00I C00I C00K 120.23(17) . . ?
C00K C00J C00G 120.1(3) . . ?
H00J C00J C00G 119.97(19) . . ?
H00J C00J C00K 119.97(17) . . ?
C00J C00K C00I 121.0(3) . . ?
H00K C00K C00I 119.51(17) . . ?
H00K C00K C00J 119.51(17) . . ?
C00O C00L O003 110.3(2) . . ?
H00e C00L O003 109.60(14) . . ?
H00e C00L C00O 109.60(18) . . ?
H00l C00L O003 109.60(14) . . ?
H00l C00L C00O 109.60(18) . . ?
H00l C00L H00e 108.1 . . ?
C00N C00M C00F 121.8(3) . . ?
H00M C00M C00F 119.10(16) . . ?
H00M C00M C00N 119.10(18) . . ?
C00M C00N C00H 120.6(3) . . ?
H00N C00N C00H 119.71(18) . . ?
H00N C00N C00M 119.71(18) . . ?
H00o C00O C00L 109.5 . . ?
H00p C00O C00L 109.5 . . ?
H00p C00O H00o 109.5 . . ?
H00q C00O C00L 109.5 . . ?
H00q C00O H00o 109.5 . . ?
H00q C00O H00p 109.5 . . ?

_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 1.754
_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_exp_5414
_audit_block_doi                 10.5517/ccdc.csd.cc1zv612
_database_code_depnum_ccdc_archive 'CCDC 1842424'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_audit_creation_date             2018-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_formula_moiety         'C20 H14 N2'
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.35
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_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

_symmetry_Int_Tables_number      14
_cell_length_a                   7.0181(4)
_cell_length_b                   7.9004(5)
_cell_length_c                   25.5706(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.661(6)
_cell_angle_gamma                90
_cell_volume                     1416.25(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1694
_cell_measurement_theta_max      27.2690
_cell_measurement_theta_min      3.8940
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3241
_exptl_crystal_F_000             592.2198
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_av_unetI/netI     0.1494
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8270
_diffrn_reflns_theta_full        24.9969
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.52
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9908
_diffrn_measured_fraction_theta_max 0.9908
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  81.00   1.00   14.00    --   15.34  77.00  60.00   87
  2  ω     58.00  83.00   1.00   14.00    --   15.34  77.00  90.00   25
  3  ω     55.00  81.00   1.00   14.00    --   15.34  77.00-150.00   26
  4  ω     -6.00  78.00   1.00   14.00    --   15.34  77.00-180.00   84
  5  ω    -38.00  35.00   1.00   14.00    --  -16.12  77.00 -60.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0954363000
_diffrn_orient_matrix_UB_12      -0.0183061000
_diffrn_orient_matrix_UB_13      -0.0060288000
_diffrn_orient_matrix_UB_21      0.0017203000
_diffrn_orient_matrix_UB_22      0.0734096000
_diffrn_orient_matrix_UB_23      -0.0159570000
_diffrn_orient_matrix_UB_31      0.0334335000
_diffrn_orient_matrix_UB_32      0.0483609000
_diffrn_orient_matrix_UB_33      0.0219199000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                1323
_reflns_number_total             2485
_reflns_odcompleteness_completeness 98.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.5256
_refine_diff_density_min         -0.4503
_refine_diff_density_rms         0.1159
_refine_ls_d_res_high            0.8410
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_refine_ls_d_res_low             5.7913
_refine_ls_goodness_of_fit_ref   0.9616
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0701
_refine_ls_restrained_S_all      0.9616
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.2151
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00M(H00M), C00L(H00L), C00J(H00J), C008(H008), C00C(H00C),
 C00F(H00F), C00G(H00G), C00I(H00I), C00E(H00E), C00D(H00D)
2.b Idealised Me refined as rotating group:
 C00H(H00a,H00b,H00h)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
N001 N 0.4254(3) 0.3946(3) 0.59701(10) 0.0450(7) Uani 1.000000 .
N002 N 0.7139(4) 0.2696(3) 0.58846(10) 0.0505(7) Uani 1.000000 .
C003 C 0.5063(4) 0.4896(3) 0.70104(12) 0.0438(8) Uani 1.000000 .
C004 C 0.6497(4) 0.4010(3) 0.67371(11) 0.0421(8) Uani 1.000000 .
C005 C 0.6038(4) 0.3531(3) 0.62003(12) 0.0437(8) Uani 1.000000 .
C006 C 0.7190(5) 0.4904(3) 0.77937(12) 0.0480(8) Uani 1.000000 .
C007 C 0.6029(5) 0.2555(3) 0.54211(12) 0.0481(8) Uani 1.000000 .
C008 C 0.8226(4) 0.3627(3) 0.69848(12) 0.0448(8) Uani 1.000000 .
C009 C 0.2889(4) 0.4858(3) 0.62356(13) 0.0467(8) Uani 1.000000 .
C00A C 0.8621(4) 0.4062(3) 0.75126(12) 0.0456(8) Uani 1.000000 .
C00B C 0.4243(4) 0.3313(3) 0.54585(12) 0.0474(8) Uani 1.000000 .
C00C C 0.5456(5) 0.5309(4) 0.75295(13) 0.0508(9) Uani 1.000000 .
C00D C 0.3292(4) 0.5305(3) 0.67299(13) 0.0476(8) Uani 1.000000 .
C00E C 0.7592(5) 0.5327(4) 0.83263(13) 0.0600(9) Uani 1.000000 .
C00F C 1.0413(5) 0.3712(4) 0.77747(13) 0.0561(9) Uani 1.000000 .
C00G C 1.0746(5) 0.4159(4) 0.82839(14) 0.0637(10) Uani 1.000000 .
C00H C 0.1032(4) 0.5283(4) 0.59508(13) 0.0607(10) Uani 1.000000 .
C00I C 0.9330(6) 0.4969(4) 0.85653(14) 0.0646(10) Uani 1.000000 .
C00J C 0.6531(5) 0.1814(4) 0.49528(13) 0.0598(10) Uani 1.000000 .
C00K C 0.2958(5) 0.3317(4) 0.50331(14) 0.0659(10) Uani 1.000000 .
C00L C 0.5251(6) 0.1840(4) 0.45330(13) 0.0671(10) Uani 1.000000 .
C00M C 0.3477(6) 0.2581(4) 0.45765(15) 0.0713(11) Uani 1.000000 .
H00K H 0.1762(5) 0.3811(4) 0.50563(14) 0.0790(12) Uiso 1.000000 R
H00M H 0.2618(6) 0.2578(4) 0.42885(15) 0.0856(13) Uiso 1.000000 R
H00L H 0.5573(6) 0.1359(4) 0.42172(13) 0.0805(12) Uiso 1.000000 R
H00J H 0.7720(5) 0.1309(4) 0.49259(13) 0.0717(12) Uiso 1.000000 R
H008 H 0.9150(4) 0.3070(3) 0.68002(12) 0.0538(10) Uiso 1.000000 R
H00C H 0.4533(5) 0.5879(4) 0.77106(13) 0.0610(10) Uiso 1.000000 R
H00F H 1.1364(5) 0.3173(4) 0.75956(13) 0.0674(11) Uiso 1.000000 R
H00G H 1.1925(5) 0.3925(4) 0.84488(14) 0.0764(12) Uiso 1.000000 R
H00I H 0.9577(6) 0.5261(4) 0.89142(14) 0.0776(12) Uiso 1.000000 R
H00E H 0.6662(5) 0.5856(4) 0.85157(13) 0.0720(11) Uiso 1.000000 R
H00D H 0.2382(4) 0.5914(3) 0.69043(13) 0.0572(10) Uiso 1.000000 R
H00a H 0.1273(5) 0.595(2) 0.5647(4) 0.0910(15) Uiso 1.000000 GR
H00b H 0.0391(14) 0.4257(4) 0.5845(7) 0.0910(15) Uiso 1.000000 GR
H00h H 0.0244(12) 0.591(2) 0.6178(3) 0.0910(15) Uiso 1.000000 GR


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
N001 C005 1.398(4) . ?
N001 C009 1.399(4) . ?
N001 C00B 1.400(4) . ?
N002 C005 1.320(3) . ?
N002 C007 1.392(4) . ?
C003 C004 1.434(4) . ?
C003 C00C 1.382(4) . ?
C003 C00D 1.442(4) . ?
C004 C005 1.446(4) . ?
C004 C008 1.376(4) . ?
C006 C00A 1.426(4) . ?
C006 C00C 1.401(4) . ?
C006 C00E 1.418(4) . ?
C007 C00B 1.397(4) . ?
C007 C00J 1.393(4) . ?
C008 C00A 1.408(4) . ?
C008 H008 0.9300 . ?
C009 C00D 1.330(4) . ?
C009 C00H 1.501(4) . ?
C00A C00F 1.424(4) . ?
C00B C00K 1.380(4) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E C00I 1.369(5) . ?
C00E H00E 0.9300 . ?
C00F C00G 1.359(4) . ?
C00F H00F 0.9300 . ?
C00G C00I 1.407(5) . ?
C00G H00G 0.9300 . ?
C00H H00a 0.9600 . ?
C00H H00b 0.9600 . ?
C00H H00h 0.9600 . ?
C00I H00I 0.9300 . ?
C00J C00L 1.367(5) . ?
C00J H00J 0.9300 . ?
C00K C00M 1.369(5) . ?
C00K H00K 0.9300 . ?
C00L C00M 1.385(5) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?

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
C009 N001 C005 122.4(3) . . ?
C00B N001 C005 106.0(2) . . ?
C00B N001 C009 131.5(3) . . ?
C007 N002 C005 103.9(3) . . ?
C00C C003 C004 118.0(3) . . ?
C00D C003 C004 118.4(3) . . ?
C00D C003 C00C 123.6(3) . . ?
C005 C004 C003 117.4(3) . . ?
C008 C004 C003 120.5(3) . . ?
C008 C004 C005 122.2(3) . . ?
N002 C005 N001 113.5(3) . . ?
C004 C005 N001 119.6(3) . . ?
C004 C005 N002 126.9(3) . . ?
C00C C006 C00A 118.6(3) . . ?
C00E C006 C00A 118.7(3) . . ?
C00E C006 C00C 122.6(3) . . ?
C00B C007 N002 112.1(3) . . ?
C00J C007 N002 127.7(3) . . ?
C00J C007 C00B 120.2(3) . . ?
C00A C008 C004 121.2(3) . . ?
H008 C008 C004 119.41(18) . . ?
H008 C008 C00A 119.41(17) . . ?
C00D C009 N001 118.5(3) . . ?
C00H C009 N001 118.6(3) . . ?
C00H C009 C00D 122.9(3) . . ?
C008 C00A C006 119.0(3) . . ?
C00F C00A C006 118.7(3) . . ?
C00F C00A C008 122.3(3) . . ?
C007 C00B N001 104.5(3) . . ?
C00K C00B N001 135.3(3) . . ?
C00K C00B C007 120.2(3) . . ?
C006 C00C C003 122.6(3) . . ?
H00C C00C C003 118.68(17) . . ?
H00C C00C C006 118.68(18) . . ?
C009 C00D C003 123.6(3) . . ?
H00D C00D C003 118.20(17) . . ?
H00D C00D C009 118.20(17) . . ?
C00I C00E C006 120.9(3) . . ?
H00E C00E C006 119.6(2) . . ?
H00E C00E C00I 119.6(2) . . ?
C00G C00F C00A 120.6(3) . . ?
H00F C00F C00A 119.69(19) . . ?
H00F C00F C00G 119.7(2) . . ?
C00I C00G C00F 120.9(3) . . ?
H00G C00G C00F 119.5(2) . . ?
H00G C00G C00I 119.5(2) . . ?
H00a C00H C009 109.5 . . ?
H00b C00H C009 109.5 . . ?
H00b C00H H00a 109.5 . . ?
H00h C00H C009 109.5 . . ?
H00h C00H H00a 109.5 . . ?
H00h C00H H00b 109.5 . . ?
C00G C00I C00E 120.1(3) . . ?
H00I C00I C00E 119.9(2) . . ?
H00I C00I C00G 119.9(2) . . ?
C00L C00J C007 119.0(3) . . ?
H00J C00J C007 120.5(2) . . ?
H00J C00J C00L 120.5(2) . . ?
C00M C00K C00B 118.7(4) . . ?
H00K C00K C00B 120.6(2) . . ?
H00K C00K C00M 120.6(2) . . ?
C00M C00L C00J 120.2(3) . . ?
H00L C00L C00J 119.9(2) . . ?
H00L C00L C00M 119.9(2) . . ?
C00L C00M C00K 121.6(4) . . ?
H00M C00M C00K 119.2(2) . . ?
H00M C00M C00L 119.2(2) . . ?

_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 3.096
_oxdiff_exptl_absorpt_empirical_full_min 0.594
####################################################################### 
# 
# 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_exp_4320
_audit_block_doi                 10.5517/ccdc.csd.cc1z0xd9
_database_code_depnum_ccdc_archive 'CCDC 1818131'
_audit_update_record             
;
2018-01-19 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_cell_formula_units_Z            4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_length_a                   5.7290(15)
_cell_length_b                   14.295(5)
_cell_length_c                   15.456(4)
_cell_volume                     1265.9(6)
_cell_measurement_reflns_used    424
_cell_measurement_theta_min      4.0260
_cell_measurement_theta_max      19.7470
_chemical_formula_moiety         'C16 H12 N2, H2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.30
_exptl_crystal_description       block
_diffrn_measurement_device_type  agilent
_diffrn_ambient_temperature      294.29(18)
_cell_measurement_temperature    294.29(18)
_diffrn_measured_fraction_theta_full 0.9152
_diffrn_measured_fraction_theta_max 0.9152
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.1365
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4004
_diffrn_reflns_theta_full        24.9988
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_F_000             528.2210
_exptl_crystal_density_diffrn    1.3133

_refine_diff_density_max         0.3860
_refine_diff_density_min         -0.3832
_refine_diff_density_rms         0.0961
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0744
_refine_ls_abs_structure_Flack   8.2(9)
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.1477
_refine_ls_goodness_of_fit_ref   1.0593
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0593
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.1071
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0171P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_reflns_Friedel_coverage         0.794
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                1289
_reflns_number_total             2039
_reflns_threshold_expression     I>=2u(I)
_space_group_IT_number           19
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_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+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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
C4 C -0.7509(7) -0.4762(3) -0.6746(3) 0.0373(10) Uani 1.000000
C5 C -0.9522(7) -0.5139(3) -0.6313(3) 0.0374(10) Uani 1.000000
C7 C -0.8181(8) -0.5893(3) -0.7901(3) 0.0504(13) Uani 1.000000
H7 H -0.7750(8) -0.6132(3) -0.8437(3) 0.0605(16) Uiso 1.000000
C8 C -0.6184(8) -0.4032(3) -0.6383(3) 0.0469(12) Uani 1.000000
H8 H -0.6583(8) -0.3789(3) -0.5845(3) 0.0563(15) Uiso 1.000000
C9 C -0.6878(7) -0.5123(3) -0.7556(3) 0.0428(11) Uani 1.000000
C13 C -0.3694(8) -0.4030(4) -0.7634(3) 0.0621(15) Uani 1.000000
H13 H -0.2416(8) -0.3788(4) -0.7930(3) 0.0746(18) Uiso 1.000000
C18 C -0.4290(8) -0.3676(3) -0.6828(3) 0.0582(14) Uani 1.000000
H18 H -0.3409(8) -0.3196(3) -0.6586(3) 0.0699(16) Uiso 1.000000
C0aa C -0.4979(8) -0.4733(3) -0.7993(3) 0.0582(14) Uani 1.000000
H0aa H -0.4584(8) -0.4956(3) -0.8538(3) 0.0699(16) Uiso 1.000000
O1aa O -0.0303(6) -0.2974(3) -0.4921(3) 0.0992(13) Uani 1.000000
H1aa H -0.023(8) -0.3556(9) -0.503(4) 0.149(2) Uiso 1.000000
H1ab H -0.171(3) -0.279(3) -0.495(5) 0.149(2) Uiso 1.000000
N1aa N -1.0641(5) -0.5915(2) -0.6691(2) 0.0372(9) Uani 1.000000
C2aa C -0.9997(8) -0.6287(3) -0.7486(3) 0.0433(11) Uani 1.000000
C3aa C -1.2366(8) -0.5486(3) -0.5456(3) 0.0399(11) Uani 1.000000
C7aa C -1.4011(8) -0.5485(3) -0.4797(3) 0.0517(13) Uani 1.000000
H7aa H -1.3949(8) -0.5043(3) -0.4356(3) 0.0621(15) Uiso 1.000000
C4aa C -1.2500(8) -0.6140(3) -0.6128(3) 0.0397(11) Uani 1.000000
C6aa C -1.5743(8) -0.6157(4) -0.4812(3) 0.0619(14) Uani 1.000000
H6aa H -1.6856(8) -0.6168(4) -0.4374(3) 0.0743(17) Uiso 1.000000
C5aa C -1.4254(7) -0.6820(3) -0.6148(3) 0.0489(12) Uani 1.000000
H5aa H -1.4347(7) -0.7254(3) -0.6595(3) 0.0587(15) Uiso 1.000000
N16 N -1.0494(6) -0.4871(2) -0.5581(2) 0.0420(9) Uani 1.000000
C17 C -1.5844(8) -0.6819(3) -0.5476(3) 0.0611(14) Uani 1.000000
H17 H -1.7012(8) -0.7271(3) -0.5466(3) 0.0733(17) Uiso 1.000000
C1 C -1.1365(8) -0.7099(3) -0.7834(3) 0.0663(15) Uani 1.000000
H1a H -1.2970(13) -0.6920(7) -0.7900(19) 0.099(2) Uiso 1.000000
H1b H -1.074(3) -0.7281(14) -0.8385(10) 0.099(2) Uiso 1.000000
H1c H -1.126(4) -0.7615(8) -0.7438(10) 0.099(2) Uiso 1.000000


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C4 C9 1.402(5) .
C4 C8 1.407(5) .
C4 C5 1.439(5) .
C5 N16 1.318(5) .
C5 N1aa 1.408(5) .
C7 C2aa 1.346(6) .
C7 C9 1.433(5) .
C8 C18 1.382(6) .
C9 C0aa 1.397(5) .
C13 C0aa 1.363(6) .
C13 C18 1.387(6) .
N1aa C2aa 1.389(5) .
N1aa C4aa 1.413(5) .
C2aa C1 1.500(6) .
C3aa C7aa 1.388(5) .
C3aa C4aa 1.399(5) .
C3aa N16 1.400(5) .
C7aa C6aa 1.380(5) .
C4aa C5aa 1.398(5) .
C6aa C17 1.398(6) .
C5aa C17 1.381(5) .

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
C8 C4 C5 121.7(4) . .
C9 C4 C5 118.9(4) . .
C9 C4 C8 119.4(4) . .
N1aa C5 C4 117.9(4) . .
N16 C5 C4 129.0(4) . .
N16 C5 N1aa 113.1(4) . .
C2aa C7 C9 123.1(4) . .
C18 C8 C4 119.9(4) . .
C7 C9 C4 118.8(4) . .
C0aa C9 C4 119.0(4) . .
C0aa C9 C7 122.2(4) . .
C0aa C13 C18 120.1(5) . .
C13 C18 C8 120.4(5) . .
C13 C0aa C9 121.2(5) . .
C2aa N1aa C5 123.2(4) . .
C4aa N1aa C5 105.5(3) . .
C4aa N1aa C2aa 131.2(4) . .
N1aa C2aa C7 117.8(4) . .
C1 C2aa C7 123.8(4) . .
C1 C2aa N1aa 118.3(4) . .
C4aa C3aa C7aa 120.5(4) . .
N16 C3aa C7aa 128.3(4) . .
N16 C3aa C4aa 111.1(4) . .
C6aa C7aa C3aa 118.4(4) . .
C3aa C4aa N1aa 105.3(4) . .
C5aa C4aa N1aa 133.3(4) . .
C5aa C4aa C3aa 121.4(4) . .
C17 C6aa C7aa 120.9(4) . .
C17 C5aa C4aa 117.2(4) . .
C3aa N16 C5 105.0(3) . .
C5aa C17 C6aa 121.7(4) . .


