# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_OXP-BPE
_database_code_depnum_ccdc_archive 'CCDC 1062956'
_audit_update_record             
;
2015-05-04 deposited with the CCDC.
2016-03-28 downloaded from the CCDC.
;

_vrf_PLAT230_OXP-BPE             
;
PROBLEM: Hirshfeld Test Diff for    N1     --  C1      ..        8.9 su    
RESPONSE: The chemical composition is correct and all the sorrounding atoms are
assigned accurately. The error could be due to thermal vibration of N1 and C1
atoms.
;
_vrf_PLAT355_OXP-BPE             
;
PROBLEM: Long    O-H (X0.82,N0.98A) O3     -   H3     ...       1.11 Ang.  
RESPONSE: The O-H is involved in a strong intermolecular hydrogen bond.
;

_audit_creation_date             2015-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            Oxaprozin-1,2-bis(4-pyridyl)ethane
_chemical_name_systematic        
'1:0.5 Cocrystal of Oxaprozin and 1,2-bis(4-pyridyl)ethane'
_chemical_formula_moiety         'C18 H15 N O3, C6 H6 N'
_chemical_formula_sum            'C24 H21 N2 O3'
_chemical_formula_weight         385.43
_chemical_melting_point          407.5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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'

_cell_length_a                   9.7069(19)
_cell_length_b                   10.878(2)
_cell_length_c                   10.907(2)
_cell_angle_alpha                76.50(3)
_cell_angle_beta                 68.03(3)
_cell_angle_gamma                66.04(3)
_cell_volume                     971.5(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3080
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      30.9451
_cell_measurement_theta_min      2.0229
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.44
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13713
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.62
_diffrn_ambient_temperature      110.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             5409
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0235
_diffrn_orient_matrix_UB_12      -0.1072
_diffrn_orient_matrix_UB_13      0.0453
_diffrn_orient_matrix_UB_21      -0.0856
_diffrn_orient_matrix_UB_22      0.0501
_diffrn_orient_matrix_UB_23      -0.0195
_diffrn_orient_matrix_UB_31      0.0263
_diffrn_orient_matrix_UB_32      -0.0114
_diffrn_orient_matrix_UB_33      -0.0951
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4067
_reflns_number_total             4686
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0766P)²+0.3623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1406
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C8(H8), C12(H12), C16(H16), C15(H15), C9(H9), C11(H11),
 C17(H17), C10(H10), C20(H20), C23(H23), C19(H19), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O2 O -0.12458(12) 0.67766(11) 0.44794(10) 0.0272(2) Uani 1 d . . .
N1 N 0.50960(12) 0.51222(11) 0.29145(10) 0.0182(2) Uani 1 d . . .
O1 O 0.40018(11) 0.42704(10) 0.20274(10) 0.0251(2) Uani 1 d . . .
O3 O -0.14364(12) 0.81303(12) 0.26130(11) 0.0343(3) Uani 1 d . . .
N2 N 0.54556(14) 0.89172(13) 0.37212(12) 0.0279(3) Uani 1 d . . .
C13 C 0.79684(15) 0.39541(13) 0.18881(12) 0.0190(3) Uani 1 d . . .
C7 C 0.62059(15) 0.25531(13) 0.06870(12) 0.0195(3) Uani 1 d . . .
C18 C 0.91984(15) 0.34328(14) 0.07503(13) 0.0211(3) Uani 1 d . . .
H18 H 0.8962 0.3234 0.0065 0.025 Uiso 1 calc . . R
C14 C 0.83389(16) 0.42662(13) 0.28739(13) 0.0215(3) Uani 1 d . . .
H14 H 0.7513 0.4656 0.3635 0.026 Uiso 1 calc . . R
C8 C 0.54060(16) 0.26852(14) -0.02009(13) 0.0225(3) Uani 1 d . . .
H8 H 0.4548 0.3495 -0.0286 0.027 Uiso 1 calc . . R
C12 C 0.74697(16) 0.13542(13) 0.07938(13) 0.0217(3) Uani 1 d . . .
H12 H 0.8021 0.1252 0.1392 0.026 Uiso 1 calc . . R
C16 C 1.11193(16) 0.34760(14) 0.16182(14) 0.0239(3) Uani 1 d . . .
H16 H 1.2191 0.3298 0.1535 0.029 Uiso 1 calc . . R
C5 C 0.11301(15) 0.67161(14) 0.26489(13) 0.0214(3) Uani 1 d . . .
H5A H 0.1439 0.7502 0.2161 0.026 Uiso 1 calc . . R
H5B H 0.1369 0.6111 0.1987 0.026 Uiso 1 calc . . R
C6 C -0.06355(15) 0.72083(13) 0.33631(13) 0.0214(3) Uani 1 d . . .
C15 C 0.99049(17) 0.40101(14) 0.27454(14) 0.0240(3) Uani 1 d . . .
H15 H 1.0149 0.4200 0.3431 0.029 Uiso 1 calc . . R
C9 C 0.58615(17) 0.16389(15) -0.09553(14) 0.0271(3) Uani 1 d . . .
H9 H 0.5314 0.1735 -0.1554 0.032 Uiso 1 calc . . R
C11 C 0.79237(17) 0.03143(14) 0.00335(14) 0.0250(3) Uani 1 d . . .
H11 H 0.8788 -0.0494 0.0108 0.030 Uiso 1 calc . . R
C2 C 0.56399(15) 0.36353(13) 0.15379(12) 0.0199(3) Uani 1 d . . .
C3 C 0.63139(15) 0.41730(13) 0.20670(13) 0.0202(3) Uani 1 d . . .
C17 C 1.07610(16) 0.32040(14) 0.06133(14) 0.0232(3) Uani 1 d . . .
H17 H 1.1586 0.2861 -0.0168 0.028 Uiso 1 calc . . R
C4 C 0.21331(15) 0.59585(14) 0.35721(13) 0.0231(3) Uani 1 d . . .
H4A H 0.2178 0.6618 0.4033 0.028 Uiso 1 calc . . R
H4B H 0.1621 0.5363 0.4255 0.028 Uiso 1 calc . . R
C1 C 0.37738(16) 0.51301(14) 0.28399(13) 0.0229(3) Uani 1 d . . .
C21 C 0.21544(16) 0.97030(15) 0.48537(14) 0.0257(3) Uani 1 d . . .
C10 C 0.71160(18) 0.04524(15) -0.08386(14) 0.0278(3) Uani 1 d . . .
H10 H 0.7423 -0.0264 -0.1353 0.033 Uiso 1 calc . . R
C20 C 0.28585(17) 1.05578(15) 0.39210(15) 0.0278(3) Uani 1 d . . .
H20 H 0.2221 1.1434 0.3654 0.033 Uiso 1 calc . . R
C23 C 0.47873(19) 0.80921(17) 0.46257(17) 0.0350(4) Uani 1 d . . .
H23 H 0.5456 0.7227 0.4883 0.042 Uiso 1 calc . . R
C19 C 0.44931(17) 1.01299(15) 0.33807(15) 0.0277(3) Uani 1 d . . .
H19 H 0.4953 1.0727 0.2737 0.033 Uiso 1 calc . . R
C22 C 0.31607(19) 0.84437(17) 0.52043(16) 0.0342(4) Uani 1 d . . .
H22 H 0.2733 0.7824 0.5841 0.041 Uiso 1 calc . . R
C24 C 0.03733(17) 1.0115(2) 0.54408(16) 0.0366(4) Uani 1 d . . .
H24A H -0.0086 1.1084 0.5588 0.044 Uiso 1 calc . . R
H24B H 0.0109 0.9592 0.6315 0.044 Uiso 1 calc . . R
H3 H -0.273(3) 0.840(3) 0.313(3) 0.069(7) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C6 1.2136(17) . ?
N1 C3 1.3982(17) . ?
N1 C1 1.3126(17) . ?
O1 C2 1.3912(16) . ?
O1 C1 1.3346(17) . ?
O3 C6 1.3188(17) . ?
O3 H3 1.11(3) . ?
N2 C23 1.334(2) . ?
N2 C19 1.335(2) . ?
C13 C18 1.3990(18) . ?
C13 C14 1.3998(18) . ?
C13 C3 1.4665(18) . ?
C7 C8 1.4030(18) . ?
C7 C12 1.3986(19) . ?
C7 C2 1.4670(19) . ?
C18 H18 0.9500 . ?
C18 C17 1.3879(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3867(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.3861(19) . ?
C16 H16 0.9500 . ?
C16 C15 1.390(2) . ?
C16 C17 1.3892(19) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5104(18) . ?
C5 C4 1.5282(18) . ?
C15 H15 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.388(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.392(2) . ?
C2 C3 1.3617(19) . ?
C17 H17 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C1 1.4849(19) . ?
C21 C20 1.386(2) . ?
C21 C22 1.387(2) . ?
C21 C24 1.509(2) . ?
C10 H10 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.382(2) . ?
C23 H23 0.9500 . ?
C23 C22 1.384(2) . ?
C19 H19 0.9500 . ?
C22 H22 0.9500 . ?
C24 C24 1.514(3) 2_576 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 105.27(11) . . ?
C1 O1 C2 105.41(11) . . ?
C6 O3 H3 110.1(13) . . ?
C23 N2 C19 117.57(13) . . ?
C18 C13 C14 118.79(12) . . ?
C18 C13 C3 121.48(12) . . ?
C14 C13 C3 119.73(12) . . ?
C8 C7 C2 119.44(12) . . ?
C12 C7 C8 118.94(12) . . ?
C12 C7 C2 121.51(12) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.60(12) . . ?
C17 C18 H18 119.7 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.38(13) . . ?
C15 C14 H14 119.8 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.34(13) . . ?
C9 C8 H8 119.8 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.46(13) . . ?
C11 C12 H12 119.8 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.81(12) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C6 C5 C4 113.66(11) . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
O2 C6 O3 124.10(13) . . ?
O2 C6 C5 123.95(12) . . ?
O3 C6 C5 111.91(12) . . ?
C14 C15 C16 120.30(12) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.19(13) . . ?
C10 C9 H9 119.9 . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.14(13) . . ?
C10 C11 H11 119.9 . . ?
O1 C2 C7 116.25(11) . . ?
C3 C2 O1 107.48(11) . . ?
C3 C2 C7 136.16(12) . . ?
N1 C3 C13 119.00(12) . . ?
C2 C3 N1 108.17(11) . . ?
C2 C3 C13 132.82(12) . . ?
C18 C17 C16 120.06(13) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C1 C4 C5 112.02(11) . . ?
C1 C4 H4A 109.2 . . ?
C1 C4 H4B 109.2 . . ?
N1 C1 O1 113.66(12) . . ?
N1 C1 C4 126.57(12) . . ?
O1 C1 C4 119.77(12) . . ?
C20 C21 C22 116.97(13) . . ?
C20 C21 C24 121.43(15) . . ?
C22 C21 C24 121.59(15) . . ?
C9 C10 C11 119.92(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C21 C20 H20 120.1 . . ?
C19 C20 C21 119.70(14) . . ?
C19 C20 H20 120.1 . . ?
N2 C23 H23 118.6 . . ?
N2 C23 C22 122.73(15) . . ?
C22 C23 H23 118.6 . . ?
N2 C19 C20 123.08(14) . . ?
N2 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 119.94(15) . . ?
C23 C22 H22 120.0 . . ?
C21 C24 C24 112.63(16) . 2_576 ?
C21 C24 H24A 109.1 . . ?
C21 C24 H24B 109.1 . . ?
C24 C24 H24A 109.1 2_576 . ?
C24 C24 H24B 109.1 2_576 . ?
H24A C24 H24B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 N1 1.45(14) . . . . ?
O1 C2 C3 C13 -177.34(13) . . . . ?
N2 C23 C22 C21 -0.4(3) . . . . ?
C13 C18 C17 C16 0.8(2) . . . . ?
C13 C14 C15 C16 1.8(2) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C7 C12 C11 C10 -0.4(2) . . . . ?
C7 C2 C3 N1 -174.31(14) . . . . ?
C7 C2 C3 C13 6.9(3) . . . . ?
C18 C13 C14 C15 -2.6(2) . . . . ?
C18 C13 C3 N1 -156.30(12) . . . . ?
C18 C13 C3 C2 22.4(2) . . . . ?
C14 C13 C18 C17 1.3(2) . . . . ?
C14 C13 C3 N1 23.92(18) . . . . ?
C14 C13 C3 C2 -157.40(15) . . . . ?
C8 C7 C12 C11 0.0(2) . . . . ?
C8 C7 C2 O1 37.25(17) . . . . ?
C8 C7 C2 C3 -147.26(16) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C12 C7 C8 C9 0.2(2) . . . . ?
C12 C7 C2 O1 -138.92(13) . . . . ?
C12 C7 C2 C3 36.6(2) . . . . ?
C12 C11 C10 C9 0.5(2) . . . . ?
C5 C4 C1 N1 129.67(14) . . . . ?
C5 C4 C1 O1 -51.65(17) . . . . ?
C6 C5 C4 C1 161.95(12) . . . . ?
C15 C16 C17 C18 -1.6(2) . . . . ?
C2 O1 C1 N1 0.56(15) . . . . ?
C2 O1 C1 C4 -178.28(12) . . . . ?
C2 C7 C8 C9 -176.04(12) . . . . ?
C2 C7 C12 C11 176.22(12) . . . . ?
C3 N1 C1 O1 0.31(15) . . . . ?
C3 N1 C1 C4 179.06(13) . . . . ?
C3 C13 C18 C17 -178.52(12) . . . . ?
C3 C13 C14 C15 177.19(12) . . . . ?
C17 C16 C15 C14 0.3(2) . . . . ?
C4 C5 C6 O2 -18.04(19) . . . . ?
C4 C5 C6 O3 164.02(12) . . . . ?
C1 N1 C3 C13 177.89(12) . . . . ?
C1 N1 C3 C2 -1.09(14) . . . . ?
C1 O1 C2 C7 175.49(11) . . . . ?
C1 O1 C2 C3 -1.23(14) . . . . ?
C21 C20 C19 N2 -0.6(2) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C20 C21 C24 C24 82.7(2) . . . 2_576 ?
C23 N2 C19 C20 0.1(2) . . . . ?
C19 N2 C23 C22 0.4(2) . . . . ?
C22 C21 C20 C19 0.6(2) . . . . ?
C22 C21 C24 C24 -96.1(2) . . . 2_576 ?
C24 C21 C20 C19 -178.31(13) . . . . ?
C24 C21 C22 C23 178.76(15) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_OXP-SAL
_database_code_depnum_ccdc_archive 'CCDC 1062957'
_audit_update_record             
;
2015-05-04 deposited with the CCDC.
2016-03-28 downloaded from the CCDC.
;

_vrf_PLAT355_OXP-SAL             
;
PROBLEM: Long    O-H (X0.82,N0.98A) O4     -   H4     ...       1.10 Ang.
RESPONSE: The O-H is involved in a strong intermolecular hydrogen bond.
;
_vrf_PLAT230_OXP-SAL             
;
PROBLEM: Hirshfeld Test Diff for    N1     --  C1      ..       10.9 su    
RESPONSE: The chemical composition is correct and all the sorrounding atoms are
assigned accurately. The error could be due to thermal vibration of N1 and C1
atoms.
;

_audit_creation_date             2015-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            Oxaprozin-Salbutamol
_chemical_name_systematic        '1:1 Salt of Oxaprozin and Salbutamol'
_chemical_formula_moiety         'C13 H22 N O3, C18 H14 N O3'
_chemical_formula_sum            'C31 H36 N2 O6'
_chemical_formula_weight         532.62
_chemical_melting_point          445.67
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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'

_cell_length_a                   10.453(2)
_cell_length_b                   10.627(2)
_cell_length_c                   13.379(3)
_cell_angle_alpha                76.02(3)
_cell_angle_beta                 69.82(3)
_cell_angle_gamma                88.05(3)
_cell_volume                     1351.7(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2963
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      30.9628
_cell_measurement_theta_min      2.1689
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19414
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.17
_diffrn_ambient_temperature      110.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             7716
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0249
_diffrn_orient_matrix_UB_12      0.0954
_diffrn_orient_matrix_UB_13      -0.0264
_diffrn_orient_matrix_UB_21      -0.0058
_diffrn_orient_matrix_UB_22      -0.0192
_diffrn_orient_matrix_UB_23      -0.0950
_diffrn_orient_matrix_UB_31      -0.0779
_diffrn_orient_matrix_UB_32      -0.0030
_diffrn_orient_matrix_UB_33      0.0259
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6008
_reflns_number_total             6617
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0786
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0837P)²+0.7199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.1956
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C4(H4A,H4B), C25(H25A,H25B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C21(H21), C20(H20), C18(H18), C14(H14), C11(H11), C12(H12),
 C17(H17), C10(H10), C8(H8), C15(H15), C9(H9), C16(H16)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O5 O 0.93888(15) -0.19763(14) 0.39671(13) 0.0309(3) Uani 1 d . . .
O2 O -0.23705(15) 0.63454(14) 0.39613(12) 0.0307(3) Uani 1 d . . .
O3 O -0.40902(15) 0.54824(14) 0.36803(13) 0.0333(3) Uani 1 d . . .
O6 O 1.16256(17) -0.04096(16) 0.23364(14) 0.0369(4) Uani 1 d . . .
O1 O 0.05332(17) 0.84165(16) 0.06319(13) 0.0392(4) Uani 1 d . . .
O4 O 0.58377(16) 0.29321(15) 0.46667(14) 0.0367(4) Uani 1 d . . .
C19 C 0.7773(2) 0.15867(18) 0.43479(16) 0.0249(4) Uani 1 d . . .
C24 C 0.91742(19) 0.14704(18) 0.38819(15) 0.0245(4) Uani 1 d . . .
H24 H 0.9772 0.2220 0.3650 0.029 Uiso 1 calc . . R
N2 N 0.68974(18) 0.42949(16) 0.58466(14) 0.0258(3) Uani 1 d . . .
N1 N -0.04514(18) 0.64424(18) 0.14265(14) 0.0298(4) Uani 1 d . . .
C21 C 0.7416(2) -0.07126(19) 0.45621(17) 0.0276(4) Uani 1 d . . .
H21 H 0.6813 -0.1458 0.4788 0.033 Uiso 1 calc . . R
C22 C 0.8820(2) -0.08161(18) 0.41060(16) 0.0257(4) Uani 1 d . . .
C26 C 0.7233(2) 0.28832(19) 0.45399(17) 0.0262(4) Uani 1 d . . .
H26 H 0.7762 0.3596 0.3901 0.031 Uiso 1 calc . . R
C27 C 0.7438(2) 0.30518(18) 0.55812(17) 0.0268(4) Uani 1 d . . .
H27A H 0.6964 0.2315 0.6205 0.032 Uiso 1 calc . . R
H27B H 0.8423 0.3043 0.5475 0.032 Uiso 1 calc . . R
C13 C 0.1384(2) 0.5040(2) 0.06573(17) 0.0309(4) Uani 1 d . . .
C23 C 0.9719(2) 0.02823(18) 0.37479(16) 0.0246(4) Uani 1 d . . .
C4 C -0.1804(2) 0.8341(2) 0.18869(18) 0.0335(5) Uani 1 d . . .
H4A H -0.1962 0.9075 0.1334 0.040 Uiso 1 calc . . R
H4B H -0.1615 0.8704 0.2440 0.040 Uiso 1 calc . . R
C20 C 0.6902(2) 0.04883(19) 0.46844(17) 0.0267(4) Uani 1 d . . .
H20 H 0.5946 0.0558 0.5001 0.032 Uiso 1 calc . . R
C28 C 0.7209(2) 0.46530(19) 0.67792(17) 0.0273(4) Uani 1 d . . .
C3 C 0.0874(2) 0.6333(2) 0.07155(17) 0.0308(4) Uani 1 d . . .
C25 C 1.1234(2) 0.01659(19) 0.32551(17) 0.0281(4) Uani 1 d . . .
H25A H 1.1692 0.1042 0.3017 0.034 Uiso 1 calc . . R
H25B H 1.1560 -0.0363 0.3829 0.034 Uiso 1 calc . . R
C6 C -0.3171(2) 0.6351(2) 0.34282(17) 0.0293(4) Uani 1 d . . .
C29 C 0.6439(3) 0.5865(2) 0.6975(2) 0.0365(5) Uani 1 d . . .
H29A H 0.6616 0.6142 0.7565 0.055 Uiso 1 calc . . GR
H29B H 0.5458 0.5671 0.7185 0.055 Uiso 1 calc . . GR
H29C H 0.6748 0.6563 0.6300 0.055 Uiso 1 calc . . GR
C18 C 0.2777(2) 0.4851(2) 0.01750(18) 0.0347(5) Uani 1 d . . .
H18 H 0.3411 0.5581 -0.0154 0.042 Uiso 1 calc . . R
C14 C 0.0475(3) 0.3943(2) 0.11222(18) 0.0371(5) Uani 1 d . . .
H14 H -0.0471 0.4045 0.1462 0.045 Uiso 1 calc . . R
C2 C 0.1461(2) 0.7550(2) 0.02270(17) 0.0314(4) Uani 1 d . . .
C7 C 0.2757(2) 0.8131(2) -0.06248(18) 0.0308(4) Uani 1 d . . .
C11 C 0.4402(2) 0.8455(2) -0.24598(19) 0.0349(5) Uani 1 d . . .
H11 H 0.4710 0.8255 -0.3157 0.042 Uiso 1 calc . . R
C31 C 0.8739(2) 0.4937(2) 0.64384(19) 0.0341(5) Uani 1 d . . .
H31A H 0.9219 0.4145 0.6333 0.051 Uiso 1 calc . . GR
H31B H 0.8930 0.5236 0.7013 0.051 Uiso 1 calc . . GR
H31C H 0.9053 0.5613 0.5750 0.051 Uiso 1 calc . . GR
C30 C 0.6691(2) 0.3527(2) 0.77985(17) 0.0320(4) Uani 1 d . . .
H30A H 0.7242 0.2777 0.7678 0.048 Uiso 1 calc . . GR
H30B H 0.5734 0.3293 0.7939 0.048 Uiso 1 calc . . GR
H30C H 0.6762 0.3788 0.8432 0.048 Uiso 1 calc . . GR
C12 C 0.3222(2) 0.7837(2) -0.16477(18) 0.0332(5) Uani 1 d . . .
H12 H 0.2726 0.7209 -0.1789 0.040 Uiso 1 calc . . R
C17 C 0.3240(3) 0.3611(2) 0.01732(19) 0.0403(5) Uani 1 d . . .
H17 H 0.4188 0.3496 -0.0139 0.048 Uiso 1 calc . . R
C10 C 0.5131(2) 0.9363(2) -0.22535(19) 0.0371(5) Uani 1 d . . .
H10 H 0.5945 0.9779 -0.2809 0.045 Uiso 1 calc . . R
C8 C 0.3498(2) 0.9060(2) -0.04264(19) 0.0329(5) Uani 1 d . . .
H8 H 0.3190 0.9272 0.0266 0.040 Uiso 1 calc . . R
C15 C 0.0944(3) 0.2709(2) 0.10911(19) 0.0419(6) Uani 1 d . . .
H15 H 0.0313 0.1978 0.1392 0.050 Uiso 1 calc . . R
C5 C -0.3093(2) 0.7465(2) 0.24492(19) 0.0354(5) Uani 1 d . . .
H5A H -0.3250 0.7090 0.1889 0.042 Uiso 1 calc . . R
H5B H -0.3863 0.8019 0.2692 0.042 Uiso 1 calc . . R
C1 C -0.0584(2) 0.7680(2) 0.13355(18) 0.0362(5) Uani 1 d . . .
C9 C 0.4684(2) 0.9670(2) -0.1245(2) 0.0381(5) Uani 1 d . . .
H9 H 0.5188 1.0299 -0.1111 0.046 Uiso 1 calc . . R
C16 C 0.2322(3) 0.2536(2) 0.0626(2) 0.0439(6) Uani 1 d . . .
H16 H 0.2638 0.1688 0.0616 0.053 Uiso 1 calc . . R
H2A H 0.593(3) 0.422(3) 0.601(2) 0.047(8) Uiso 1 d . . .
H2B H 0.719(3) 0.500(3) 0.517(2) 0.046(8) Uiso 1 d . . .
H5 H 0.873(4) -0.256(4) 0.394(3) 0.087(12) Uiso 1 d . . .
H6 H 1.102(4) -0.109(4) 0.257(3) 0.080(12) Uiso 1 d . . .
H4 H 0.566(5) 0.397(5) 0.447(4) 0.113(16) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C22 1.376(2) . ?
O5 H5 0.96(4) . ?
O2 C6 1.272(3) . ?
O3 C6 1.256(3) . ?
O6 C25 1.432(3) . ?
O6 H6 0.90(4) . ?
O1 C2 1.378(3) . ?
O1 C1 1.346(3) . ?
O4 C26 1.410(2) . ?
O4 H4 1.10(5) . ?
C19 C24 1.394(3) . ?
C19 C26 1.517(3) . ?
C19 C20 1.389(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.393(3) . ?
N2 C27 1.493(2) . ?
N2 C28 1.525(3) . ?
N2 H2A 0.96(3) . ?
N2 H2B 0.99(3) . ?
N1 C3 1.404(3) . ?
N1 C1 1.299(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.394(3) . ?
C21 C20 1.392(3) . ?
C22 C23 1.403(3) . ?
C26 H26 1.0000 . ?
C26 C27 1.532(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C13 C3 1.467(3) . ?
C13 C18 1.404(3) . ?
C13 C14 1.403(3) . ?
C23 C25 1.505(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.515(3) . ?
C4 C1 1.484(3) . ?
C20 H20 0.9500 . ?
C28 C29 1.524(3) . ?
C28 C31 1.523(3) . ?
C28 C30 1.527(3) . ?
C3 C2 1.358(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C6 C5 1.519(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C17 1.389(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(4) . ?
C2 C7 1.473(3) . ?
C7 C12 1.394(3) . ?
C7 C8 1.401(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C11 C10 1.383(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C12 H12 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.390(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.383(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C9 H9 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O5 H5 110(2) . . ?
C25 O6 H6 102(2) . . ?
C1 O1 C2 105.15(18) . . ?
C26 O4 H4 105(2) . . ?
C24 C19 C26 119.79(17) . . ?
C20 C19 C24 118.98(17) . . ?
C20 C19 C26 121.13(17) . . ?
C19 C24 H24 119.2 . . ?
C23 C24 C19 121.63(18) . . ?
C23 C24 H24 119.2 . . ?
C27 N2 C28 115.95(15) . . ?
C27 N2 H2A 106.3(17) . . ?
C27 N2 H2B 109.4(17) . . ?
C28 N2 H2A 110.6(17) . . ?
C28 N2 H2B 111.9(17) . . ?
H2A N2 H2B 102(2) . . ?
C1 N1 C3 105.21(18) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.62(18) . . ?
O5 C22 C21 122.32(18) . . ?
O5 C22 C23 116.99(17) . . ?
C21 C22 C23 120.68(18) . . ?
O4 C26 C19 111.02(16) . . ?
O4 C26 H26 109.3 . . ?
O4 C26 C27 110.02(17) . . ?
C19 C26 H26 109.3 . . ?
C19 C26 C27 107.84(16) . . ?
C27 C26 H26 109.3 . . ?
N2 C27 C26 111.30(16) . . ?
N2 C27 H27A 109.4 . . ?
N2 C27 H27B 109.4 . . ?
C26 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C18 C13 C3 122.00(19) . . ?
C14 C13 C3 119.9(2) . . ?
C14 C13 C18 118.1(2) . . ?
C24 C23 C22 118.35(17) . . ?
C24 C23 C25 121.15(17) . . ?
C22 C23 C25 120.49(17) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C1 C4 H4A 108.7 . . ?
C1 C4 H4B 108.7 . . ?
C1 C4 C5 114.02(19) . . ?
C19 C20 C21 120.72(18) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
N2 C28 C30 108.37(16) . . ?
C29 C28 N2 106.33(16) . . ?
C29 C28 C30 110.59(18) . . ?
C31 C28 N2 109.55(17) . . ?
C31 C28 C29 110.35(18) . . ?
C31 C28 C30 111.48(18) . . ?
N1 C3 C13 119.41(19) . . ?
C2 C3 N1 107.93(19) . . ?
C2 C3 C13 132.6(2) . . ?
O6 C25 C23 113.77(17) . . ?
O6 C25 H25A 108.8 . . ?
O6 C25 H25B 108.8 . . ?
C23 C25 H25A 108.8 . . ?
C23 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
O2 C6 C5 120.91(19) . . ?
O3 C6 O2 123.54(19) . . ?
O3 C6 C5 115.52(19) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
O1 C2 C7 115.64(19) . . ?
C3 C2 O1 107.93(18) . . ?
C3 C2 C7 136.4(2) . . ?
C12 C7 C2 121.5(2) . . ?
C12 C7 C8 119.2(2) . . ?
C8 C7 C2 119.2(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(2) . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.5(2) . . ?
C11 C12 H12 119.8 . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.3(2) . . ?
C16 C17 H17 119.8 . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C9 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C4 C5 C6 118.94(19) . . ?
C4 C5 H5A 107.6 . . ?
C4 C5 H5B 107.6 . . ?
C6 C5 H5A 107.6 . . ?
C6 C5 H5B 107.6 . . ?
H5A C5 H5B 107.0 . . ?
O1 C1 C4 118.4(2) . . ?
N1 C1 O1 113.8(2) . . ?
N1 C1 C4 127.8(2) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C17 C16 H16 120.3 . . ?
C15 C16 C17 119.5(2) . . ?
C15 C16 H16 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 C22 C23 C24 -179.71(17) . . . . ?
O5 C22 C23 C25 -1.1(3) . . . . ?
O2 C6 C5 C4 19.3(3) . . . . ?
O3 C6 C5 C4 -162.7(2) . . . . ?
O1 C2 C7 C12 -124.5(2) . . . . ?
O1 C2 C7 C8 51.5(3) . . . . ?
O4 C26 C27 N2 -57.3(2) . . . . ?
C19 C24 C23 C22 -0.7(3) . . . . ?
C19 C24 C23 C25 -179.32(18) . . . . ?
C19 C26 C27 N2 -178.53(16) . . . . ?
C24 C19 C26 O4 160.71(17) . . . . ?
C24 C19 C26 C27 -78.7(2) . . . . ?
C24 C19 C20 C21 0.1(3) . . . . ?
C24 C23 C25 O6 -125.8(2) . . . . ?
N1 C3 C2 O1 0.9(2) . . . . ?
N1 C3 C2 C7 -175.6(2) . . . . ?
C21 C22 C23 C24 1.4(3) . . . . ?
C21 C22 C23 C25 -179.94(19) . . . . ?
C22 C21 C20 C19 0.6(3) . . . . ?
C22 C23 C25 O6 55.5(2) . . . . ?
C26 C19 C24 C23 176.37(17) . . . . ?
C26 C19 C20 C21 -176.27(18) . . . . ?
C27 N2 C28 C29 -174.26(17) . . . . ?
C27 N2 C28 C31 66.5(2) . . . . ?
C27 N2 C28 C30 -55.3(2) . . . . ?
C13 C3 C2 O1 -176.2(2) . . . . ?
C13 C3 C2 C7 7.2(4) . . . . ?
C13 C18 C17 C16 1.7(4) . . . . ?
C13 C14 C15 C16 1.7(3) . . . . ?
C20 C19 C24 C23 -0.1(3) . . . . ?
C20 C19 C26 O4 -22.9(3) . . . . ?
C20 C19 C26 C27 97.7(2) . . . . ?
C20 C21 C22 O5 179.81(18) . . . . ?
C20 C21 C22 C23 -1.4(3) . . . . ?
C28 N2 C27 C26 -172.35(16) . . . . ?
C3 N1 C1 O1 -0.3(2) . . . . ?
C3 N1 C1 C4 178.3(2) . . . . ?
C3 C13 C18 C17 177.2(2) . . . . ?
C3 C13 C14 C15 -178.9(2) . . . . ?
C3 C2 C7 C12 51.8(4) . . . . ?
C3 C2 C7 C8 -132.1(3) . . . . ?
C18 C13 C3 N1 -164.67(19) . . . . ?
C18 C13 C3 C2 12.2(4) . . . . ?
C18 C13 C14 C15 -0.8(3) . . . . ?
C18 C17 C16 C15 -0.8(4) . . . . ?
C14 C13 C3 N1 13.4(3) . . . . ?
C14 C13 C3 C2 -169.8(2) . . . . ?
C14 C13 C18 C17 -0.9(3) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C2 O1 C1 N1 0.8(2) . . . . ?
C2 O1 C1 C4 -177.86(19) . . . . ?
C2 C7 C12 C11 176.1(2) . . . . ?
C2 C7 C8 C9 -176.4(2) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C11 C10 C9 C8 0.3(3) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
C12 C11 C10 C9 -0.6(3) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C5 C4 C1 O1 166.7(2) . . . . ?
C5 C4 C1 N1 -11.8(3) . . . . ?
C1 O1 C2 C3 -1.0(2) . . . . ?
C1 O1 C2 C7 176.31(19) . . . . ?
C1 N1 C3 C13 177.20(19) . . . . ?
C1 N1 C3 C2 -0.4(2) . . . . ?
C1 C4 C5 C6 65.7(3) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_OXP-2A3P
_database_code_depnum_ccdc_archive 'CCDC 1062958'
_audit_update_record             
;
2015-05-04 deposited with the CCDC.
2016-03-28 downloaded from the CCDC.
;

_vrf_DIFMX01_OXP-2A3P            
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: Absorption corrections were applied and all other other sources of
error were carefully examined. The fact that all the remaining atoms were
assigned accurately assuming the residual electron density as an additional
hydrogen atom would result in unrealistic model. Nearest atom to the highest
residual election density: C5, distance: 1.10 \%A.
;

_audit_creation_date             2015-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            Oxaprozin-2-Amino-3-Picoline
_chemical_name_systematic        '1:1 Salt of Oxaprozin and 2-Amino-3-Picoline'
_chemical_formula_moiety         'C18 H14 N O3, C6 H9 N2'
_chemical_formula_sum            'C24 H23 N3 O3'
_chemical_formula_weight         401.45
_chemical_melting_point          384.67
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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'

_cell_length_a                   6.0156(12)
_cell_length_b                   8.8644(18)
_cell_length_c                   19.296(4)
_cell_angle_alpha                81.31(3)
_cell_angle_beta                 85.29(3)
_cell_angle_gamma                80.23(3)
_cell_volume                     1000.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3651
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      30.9468
_cell_measurement_theta_min      2.1390
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.44
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13806
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.14
_diffrn_ambient_temperature      110.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             5565
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.1379
_diffrn_orient_matrix_UB_12      -0.0326
_diffrn_orient_matrix_UB_13      0.0921
_diffrn_orient_matrix_UB_21      0.0243
_diffrn_orient_matrix_UB_22      -0.0643
_diffrn_orient_matrix_UB_23      -0.0929
_diffrn_orient_matrix_UB_31      0.0189
_diffrn_orient_matrix_UB_32      0.0457
_diffrn_orient_matrix_UB_33      -0.0176
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4652
_reflns_number_total             4799
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.803
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0724
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1183P)²+0.3675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2033
_refine_ls_wR_factor_ref         0.2052
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C12(H12), C18(H18), C14(H14), C8(H8), C10(H10), C16(H16), C11(H11),
 C15(H15), C9(H9), C21(H21), C23(H23), C22(H22)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.7704(2) 0.39164(16) 0.27241(7) 0.0259(3) Uani 1 d . . .
O1 O 0.9662(2) 0.58539(15) 0.26080(7) 0.0335(3) Uani 1 d . . .
O3 O 0.2090(2) 0.66730(18) 0.45246(7) 0.0416(4) Uani 1 d . . .
O2 O 0.4861(2) 0.80652(18) 0.45004(7) 0.0404(3) Uani 1 d . . .
C17 C 1.0909(3) 0.0791(2) 0.09375(9) 0.0307(4) Uani 1 d . . .
H17 H 1.2214 0.0406 0.0666 0.037 Uiso 1 calc . . R
C13 C 0.9015(3) 0.26392(18) 0.16862(8) 0.0251(3) Uani 1 d . . .
C12 C 1.1405(3) 0.58151(19) 0.07623(9) 0.0289(3) Uani 1 d . . .
H12 H 1.0147 0.5429 0.0629 0.035 Uiso 1 calc . . R
C18 C 1.0934(3) 0.20529(19) 0.12883(9) 0.0278(3) Uani 1 d . . .
H18 H 1.2258 0.2517 0.1257 0.033 Uiso 1 calc . . R
C7 C 1.1766(3) 0.57431(18) 0.14745(8) 0.0265(3) Uani 1 d . . .
C1 C 0.8171(3) 0.5076(2) 0.30023(9) 0.0318(4) Uani 1 d . . .
C3 C 0.9036(3) 0.38973(19) 0.20980(8) 0.0253(3) Uani 1 d . . .
C14 C 0.7086(3) 0.1934(2) 0.17207(9) 0.0298(4) Uani 1 d . . .
H14 H 0.5769 0.2322 0.1986 0.036 Uiso 1 calc . . R
C8 C 1.3610(3) 0.6322(2) 0.16626(9) 0.0312(4) Uani 1 d . . .
H8 H 1.3860 0.6294 0.2144 0.037 Uiso 1 calc . . R
C4 C 0.7102(3) 0.5566(2) 0.36719(9) 0.0339(4) Uani 1 d . . .
H4A H 0.8142 0.6101 0.3882 0.041 Uiso 1 calc . . R
H4B H 0.6841 0.4640 0.4006 0.041 Uiso 1 calc . . R
C10 C 1.4720(3) 0.7003(2) 0.04416(10) 0.0362(4) Uani 1 d . . .
H10 H 1.5733 0.7426 0.0091 0.043 Uiso 1 calc . . R
C2 C 1.0211(3) 0.51021(19) 0.20184(8) 0.0269(3) Uani 1 d . . .
C16 C 0.8997(3) 0.0095(2) 0.09812(10) 0.0325(4) Uani 1 d . . .
H16 H 0.8992 -0.0773 0.0747 0.039 Uiso 1 calc . . R
C5 C 0.4856(3) 0.6646(2) 0.35588(9) 0.0352(4) Uani 1 d . . .
H5A H 0.3784 0.6100 0.3370 0.042 Uiso 1 calc . . R
H5B H 0.5098 0.7556 0.3212 0.042 Uiso 1 calc . . R
C11 C 1.2874(3) 0.6448(2) 0.02480(10) 0.0340(4) Uani 1 d . . .
H11 H 1.2613 0.6499 -0.0235 0.041 Uiso 1 calc . . R
C6 C 0.3857(3) 0.7181(2) 0.42543(9) 0.0351(4) Uani 1 d . . .
C15 C 0.7076(3) 0.0682(2) 0.13738(10) 0.0332(4) Uani 1 d . . .
H15 H 0.5754 0.0217 0.1402 0.040 Uiso 1 calc . . R
C9 C 1.5088(3) 0.6943(2) 0.11454(11) 0.0350(4) Uani 1 d . . .
H9 H 1.6353 0.7326 0.1276 0.042 Uiso 1 calc . . R
N2 N 0.0032(3) 0.21991(17) 0.43642(7) 0.0296(3) Uani 1 d . . .
N3 N -0.2448(3) 0.04720(19) 0.44187(8) 0.0324(3) Uani 1 d . . .
C19 C -0.0669(3) 0.10503(19) 0.40953(8) 0.0270(3) Uani 1 d . . .
C21 C 0.2324(3) 0.1203(2) 0.32047(9) 0.0319(4) Uani 1 d . . .
H21 H 0.3145 0.0858 0.2801 0.038 Uiso 1 calc . . R
C20 C 0.0502(3) 0.0526(2) 0.34811(8) 0.0285(4) Uani 1 d . . .
C24 C -0.0323(3) -0.0699(2) 0.31644(10) 0.0363(4) Uani 1 d . . .
H24A H 0.0558 -0.0862 0.2724 0.054 Uiso 1 calc . . GR
H24B H -0.1921 -0.0374 0.3069 0.054 Uiso 1 calc . . GR
H24C H -0.0147 -0.1665 0.3492 0.054 Uiso 1 calc . . GR
C23 C 0.1828(3) 0.2872(2) 0.40801(9) 0.0326(4) Uani 1 d . . .
H23 H 0.2253 0.3679 0.4287 0.039 Uiso 1 calc . . R
C22 C 0.3022(3) 0.2394(2) 0.34996(10) 0.0341(4) Uani 1 d . . .
H22 H 0.4289 0.2851 0.3300 0.041 Uiso 1 calc . . R
H3A H -0.318(5) 0.093(4) 0.4804(16) 0.064(8) Uiso 1 d . . .
H2 H -0.089(5) 0.259(3) 0.4798(16) 0.065(8) Uiso 1 d . . .
H3B H -0.299(5) -0.032(3) 0.4265(15) 0.054(8) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.309(2) . ?
N1 C3 1.3946(19) . ?
O1 C1 1.341(2) . ?
O1 C2 1.3929(19) . ?
O3 C6 1.267(2) . ?
O2 C6 1.235(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(2) . ?
C17 C16 1.386(3) . ?
C13 C18 1.401(2) . ?
C13 C3 1.466(2) . ?
C13 C14 1.400(2) . ?
C12 H12 0.9500 . ?
C12 C7 1.399(2) . ?
C12 C11 1.392(2) . ?
C18 H18 0.9500 . ?
C7 C8 1.393(2) . ?
C7 C2 1.462(2) . ?
C1 C4 1.487(2) . ?
C3 C2 1.361(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.395(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.529(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C10 C9 1.385(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.397(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.533(2) . ?
C11 H11 0.9500 . ?
C15 H15 0.9500 . ?
C9 H9 0.9500 . ?
N2 C19 1.351(2) . ?
N2 C23 1.359(2) . ?
N2 H2 1.04(3) . ?
N3 C19 1.333(2) . ?
N3 H3A 0.94(3) . ?
N3 H3B 0.92(3) . ?
C19 C20 1.427(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.370(2) . ?
C21 C22 1.409(3) . ?
C20 C24 1.494(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C22 1.363(3) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 105.34(14) . . ?
C1 O1 C2 105.31(14) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.58(16) . . ?
C18 C13 C3 121.54(15) . . ?
C14 C13 C18 118.59(15) . . ?
C14 C13 C3 119.76(14) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C7 120.51(16) . . ?
C17 C18 C13 120.28(16) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C12 C7 C2 120.85(15) . . ?
C8 C7 C12 119.13(16) . . ?
C8 C7 C2 120.00(15) . . ?
N1 C1 O1 113.57(15) . . ?
N1 C1 C4 124.61(17) . . ?
O1 C1 C4 121.75(17) . . ?
N1 C3 C13 118.36(14) . . ?
C2 C3 N1 108.52(14) . . ?
C2 C3 C13 133.06(14) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.83(16) . . ?
C15 C14 H14 119.6 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.16(17) . . ?
C9 C8 H8 119.9 . . ?
C1 C4 H4A 109.3 . . ?
C1 C4 H4B 109.3 . . ?
C1 C4 C5 111.68(15) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.11(17) . . ?
O1 C2 C7 117.57(14) . . ?
C3 C2 O1 107.23(14) . . ?
C3 C2 C7 135.18(15) . . ?
C17 C16 H16 120.4 . . ?
C17 C16 C15 119.29(16) . . ?
C15 C16 H16 120.4 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C4 C5 C6 110.15(15) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.84(17) . . ?
C10 C11 H11 120.1 . . ?
O3 C6 C5 117.23(17) . . ?
O2 C6 O3 126.05(17) . . ?
O2 C6 C5 116.72(17) . . ?
C14 C15 C16 120.43(16) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.24(17) . . ?
C10 C9 H9 119.9 . . ?
C19 N2 C23 122.91(15) . . ?
C19 N2 H2 117.4(17) . . ?
C23 N2 H2 119.7(17) . . ?
C19 N3 H3A 117.7(18) . . ?
C19 N3 H3B 121.9(18) . . ?
H3A N3 H3B 120(3) . . ?
N2 C19 C20 118.93(16) . . ?
N3 C19 N2 117.78(15) . . ?
N3 C19 C20 123.28(16) . . ?
C20 C21 H21 118.9 . . ?
C20 C21 C22 122.21(16) . . ?
C22 C21 H21 118.9 . . ?
C19 C20 C24 119.18(16) . . ?
C21 C20 C19 117.51(16) . . ?
C21 C20 C24 123.29(16) . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C23 H23 119.8 . . ?
N2 C23 C22 120.35(17) . . ?
C22 C23 H23 119.8 . . ?
C21 C22 H22 121.0 . . ?
C23 C22 C21 118.08(17) . . ?
C23 C22 H22 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C4 C5 -84.6(2) . . . . ?
N1 C3 C2 O1 1.71(18) . . . . ?
N1 C3 C2 C7 -176.49(18) . . . . ?
O1 C1 C4 C5 92.2(2) . . . . ?
C17 C16 C15 C14 -0.6(3) . . . . ?
C13 C3 C2 O1 -175.16(16) . . . . ?
C13 C3 C2 C7 6.6(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C12 C7 C8 C9 -1.0(2) . . . . ?
C12 C7 C2 O1 -139.32(16) . . . . ?
C12 C7 C2 C3 38.7(3) . . . . ?
C18 C17 C16 C15 0.8(3) . . . . ?
C18 C13 C3 N1 -147.35(16) . . . . ?
C18 C13 C3 C2 29.3(3) . . . . ?
C18 C13 C14 C15 0.4(2) . . . . ?
C7 C12 C11 C10 0.4(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C1 N1 C3 C13 175.47(14) . . . . ?
C1 N1 C3 C2 -1.94(18) . . . . ?
C1 O1 C2 C7 177.74(14) . . . . ?
C1 O1 C2 C3 -0.82(18) . . . . ?
C1 C4 C5 C6 -177.58(16) . . . . ?
C3 N1 C1 O1 1.46(19) . . . . ?
C3 N1 C1 C4 178.55(16) . . . . ?
C3 C13 C18 C17 175.92(15) . . . . ?
C3 C13 C14 C15 -175.78(15) . . . . ?
C14 C13 C18 C17 -0.2(2) . . . . ?
C14 C13 C3 N1 28.7(2) . . . . ?
C14 C13 C3 C2 -154.67(18) . . . . ?
C8 C7 C2 O1 39.3(2) . . . . ?
C8 C7 C2 C3 -142.6(2) . . . . ?
C4 C5 C6 O3 -110.6(2) . . . . ?
C4 C5 C6 O2 69.1(2) . . . . ?
C2 O1 C1 N1 -0.4(2) . . . . ?
C2 O1 C1 C4 -177.61(16) . . . . ?
C2 C7 C8 C9 -179.61(16) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C11 C12 C7 C8 0.4(2) . . . . ?
C11 C12 C7 C2 179.04(15) . . . . ?
C11 C10 C9 C8 0.1(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
N2 C19 C20 C21 1.4(2) . . . . ?
N2 C19 C20 C24 -177.52(15) . . . . ?
N2 C23 C22 C21 0.6(3) . . . . ?
N3 C19 C20 C21 -179.19(16) . . . . ?
N3 C19 C20 C24 1.9(3) . . . . ?
C19 N2 C23 C22 -0.3(3) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C23 N2 C19 N3 179.80(16) . . . . ?
C23 N2 C19 C20 -0.7(3) . . . . ?
C22 C21 C20 C19 -1.1(3) . . . . ?
C22 C21 C20 C24 177.76(17) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_OXP-BP
_database_code_depnum_ccdc_archive 'CCDC 1062959'
_audit_update_record             
;
2015-05-04 deposited with the CCDC.
2016-03-28 downloaded from the CCDC.
;

_vrf_PLAT230_OXP-BP              
;
PROBLEM: Hirshfeld Test Diff for    N1     --  C1      ..       10.8 su    
RESPONSE: The chemical composition is correct and all the sorrounding atoms are
assigned accurately. The error could be due to thermal vibration of N1 and C1
atoms.
;

_audit_creation_date             2015-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            Oxaprozin-4,4'-Bipyridine
_chemical_name_systematic        "1:0.5 Salt of Oxaprozin and 4,4'-Bipyridine"
_chemical_formula_moiety         'C18 H15 N O3, C5 H4 N'
_chemical_formula_sum            'C23 H19 N2 O3'
_chemical_formula_weight         371.40
_chemical_melting_point          421.5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.422(3)
_cell_length_b                   15.305(3)
_cell_length_c                   18.618(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.53(3)
_cell_angle_gamma                90.00
_cell_volume                     3718.4(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5872
_cell_measurement_temperature    113.1500
_cell_measurement_theta_max      31.1216
_cell_measurement_theta_min      2.0510
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.33
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13232
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.25
_diffrn_ambient_temperature      113.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             5364
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0231
_diffrn_orient_matrix_UB_12      -0.0292
_diffrn_orient_matrix_UB_13      -0.0670
_diffrn_orient_matrix_UB_21      -0.0481
_diffrn_orient_matrix_UB_22      -0.0441
_diffrn_orient_matrix_UB_23      0.0026
_diffrn_orient_matrix_UB_31      -0.0286
_diffrn_orient_matrix_UB_32      0.0290
_diffrn_orient_matrix_UB_33      -0.0373
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4284
_reflns_number_total             4540
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0708P)²+2.5544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1462
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C12(H12), C11(H11), C9(H9), C17(H17), C16(H16), C15(H15),
 C8(H8), C10(H10), C22(H22), C20(H20), C19(H19), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.12096(8) 0.11469(7) 0.73958(6) 0.0293(2) Uani 1 d . . .
N1 N 0.15926(9) -0.02398(8) 0.72637(6) 0.0245(3) Uani 1 d . . .
O3 O -0.12992(9) -0.13997(7) 0.52194(7) 0.0361(3) Uani 1 d . . .
O2 O -0.14638(9) 0.00471(8) 0.51039(7) 0.0381(3) Uani 1 d . . .
C1 C 0.09780(11) 0.04073(10) 0.70076(8) 0.0270(3) Uani 1 d . . .
C13 C 0.30842(10) -0.04939(9) 0.82921(8) 0.0246(3) Uani 1 d . . .
C5 C -0.02860(12) -0.05361(10) 0.61670(8) 0.0288(3) Uani 1 d . . .
H5A H 0.0286 -0.0938 0.6151 0.035 Uiso 1 calc . . R
H5B H -0.0601 -0.0732 0.6570 0.035 Uiso 1 calc . . R
C6 C -0.10722(11) -0.05864(10) 0.54440(8) 0.0270(3) Uani 1 d . . .
C4 C 0.01329(11) 0.03805(10) 0.63350(8) 0.0272(3) Uani 1 d . . .
H4A H 0.0385 0.0600 0.5910 0.033 Uiso 1 calc . . R
H4B H -0.0426 0.0771 0.6403 0.033 Uiso 1 calc . . R
C2 C 0.20640(10) 0.09514(9) 0.79549(7) 0.0238(3) Uani 1 d . . .
C7 C 0.25115(11) 0.16578(9) 0.84571(8) 0.0241(3) Uani 1 d . . .
C14 C 0.34408(11) -0.11698(10) 0.79137(8) 0.0289(3) Uani 1 d . . .
H14 H 0.3176 -0.1232 0.7396 0.035 Uiso 1 calc . . R
C18 C 0.34765(11) -0.04155(10) 0.90544(8) 0.0286(3) Uani 1 d . . .
H18 H 0.3234 0.0035 0.9321 0.034 Uiso 1 calc . . R
C12 C 0.35696(11) 0.16946(10) 0.87444(8) 0.0267(3) Uani 1 d . . .
H12 H 0.3997 0.1249 0.8626 0.032 Uiso 1 calc . . R
C11 C 0.40020(12) 0.23796(10) 0.92026(8) 0.0308(3) Uani 1 d . . .
H11 H 0.4723 0.2404 0.9390 0.037 Uiso 1 calc . . R
C9 C 0.23317(13) 0.29929(10) 0.91047(9) 0.0332(3) Uani 1 d . . .
H9 H 0.1907 0.3435 0.9232 0.040 Uiso 1 calc . . R
C3 C 0.22935(10) 0.00937(10) 0.78787(8) 0.0245(3) Uani 1 d . . .
C17 C 0.42188(12) -0.09941(11) 0.94228(9) 0.0333(3) Uani 1 d . . .
H17 H 0.4488 -0.0934 0.9940 0.040 Uiso 1 calc . . R
C16 C 0.45711(13) -0.16620(11) 0.90396(9) 0.0353(4) Uani 1 d . . .
H16 H 0.5080 -0.2056 0.9294 0.042 Uiso 1 calc . . R
C15 C 0.41772(12) -0.17502(10) 0.82851(9) 0.0325(3) Uani 1 d . . .
H15 H 0.4412 -0.2209 0.8022 0.039 Uiso 1 calc . . R
C8 C 0.18958(12) 0.23161(10) 0.86367(8) 0.0286(3) Uani 1 d . . .
H8 H 0.1176 0.2303 0.8439 0.034 Uiso 1 calc . . R
C10 C 0.33844(14) 0.30258(10) 0.93859(9) 0.0342(3) Uani 1 d . . .
H10 H 0.3680 0.3490 0.9703 0.041 Uiso 1 calc . . R
N2 N 0.27803(10) 0.14059(9) 0.60235(7) 0.0307(3) Uani 1 d . . .
C22 C 0.42001(11) 0.06380(10) 0.67882(8) 0.0289(3) Uani 1 d . . .
H22 H 0.4569 0.0106 0.6902 0.035 Uiso 1 calc . . R
C21 C 0.45305(10) 0.13932(10) 0.71951(7) 0.0253(3) Uani 1 d . . .
C20 C 0.39471(11) 0.21471(10) 0.70056(8) 0.0287(3) Uani 1 d . . .
H20 H 0.4132 0.2672 0.7277 0.034 Uiso 1 calc . . R
C19 C 0.30929(11) 0.21258(11) 0.64175(8) 0.0303(3) Uani 1 d . . .
H19 H 0.2712 0.2649 0.6289 0.036 Uiso 1 calc . . R
C23 C 0.33258(12) 0.06728(11) 0.62154(9) 0.0312(3) Uani 1 d . . .
H23 H 0.3104 0.0153 0.5947 0.037 Uiso 1 calc . . R
H3 H -0.183(2) -0.1391(18) 0.4753(16) 0.073(8) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3399(18) . ?
O1 C2 1.3891(17) . ?
N1 C1 1.3057(19) . ?
N1 C3 1.3973(17) . ?
O3 C6 1.3256(19) . ?
O3 H3 0.99(3) . ?
O2 C6 1.2089(18) . ?
C1 C4 1.480(2) . ?
C13 C14 1.398(2) . ?
C13 C18 1.399(2) . ?
C13 C3 1.465(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.506(2) . ?
C5 C4 1.516(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C2 C7 1.4633(19) . ?
C2 C3 1.363(2) . ?
C7 C12 1.397(2) . ?
C7 C8 1.393(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.390(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.391(2) . ?
C9 C10 1.388(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.391(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.387(2) . ?
C15 H15 0.9500 . ?
C8 H8 0.9500 . ?
C10 H10 0.9500 . ?
N2 C19 1.336(2) . ?
N2 C23 1.342(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.396(2) . ?
C22 C23 1.390(2) . ?
C21 C21 1.486(3) 2_656 ?
C21 C20 1.393(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.388(2) . ?
C19 H19 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 105.60(12) . . ?
C1 N1 C3 105.60(12) . . ?
C6 O3 H3 109.3(16) . . ?
O1 C1 C4 120.98(13) . . ?
N1 C1 O1 113.38(13) . . ?
N1 C1 C4 125.56(13) . . ?
C14 C13 C18 118.89(13) . . ?
C14 C13 C3 118.75(13) . . ?
C18 C13 C3 122.35(13) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C6 C5 C4 112.35(12) . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
O3 C6 C5 113.04(13) . . ?
O2 C6 O3 123.24(14) . . ?
O2 C6 C5 123.72(14) . . ?
C1 C4 C5 111.95(12) . . ?
C1 C4 H4A 109.2 . . ?
C1 C4 H4B 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O1 C2 C7 117.59(12) . . ?
C3 C2 O1 107.25(12) . . ?
C3 C2 C7 135.15(13) . . ?
C12 C7 C2 120.21(13) . . ?
C8 C7 C2 120.67(13) . . ?
C8 C7 C12 119.09(13) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.71(14) . . ?
C15 C14 H14 119.6 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.19(14) . . ?
C17 C18 H18 119.9 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.44(14) . . ?
C11 C12 H12 119.8 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.15(15) . . ?
C10 C11 H11 119.9 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.33(15) . . ?
N1 C3 C13 118.19(13) . . ?
C2 C3 N1 108.17(12) . . ?
C2 C3 C13 133.64(13) . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.40(15) . . ?
C16 C17 H17 119.8 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.75(14) . . ?
C15 C16 H16 120.1 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.06(14) . . ?
C16 C15 H15 120.0 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.18(14) . . ?
C9 C8 H8 119.9 . . ?
C11 C10 C9 119.78(14) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C19 N2 C23 117.50(13) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C23 C22 C21 119.26(14) . . ?
C22 C21 C21 121.30(9) . 2_656 ?
C20 C21 C22 117.38(13) . . ?
C20 C21 C21 121.31(9) . 2_656 ?
C21 C20 H20 120.3 . . ?
C19 C20 C21 119.47(14) . . ?
C19 C20 H20 120.3 . . ?
N2 C19 C20 123.23(14) . . ?
N2 C19 H19 118.4 . . ?
C20 C19 H19 118.4 . . ?
N2 C23 C22 123.13(14) . . ?
N2 C23 H23 118.4 . . ?
C22 C23 H23 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C4 C5 -156.35(13) . . . . ?
O1 C2 C7 C12 -145.66(13) . . . . ?
O1 C2 C7 C8 32.28(19) . . . . ?
O1 C2 C3 N1 1.06(16) . . . . ?
O1 C2 C3 C13 -179.20(14) . . . . ?
N1 C1 C4 C5 27.1(2) . . . . ?
C1 O1 C2 C7 178.01(12) . . . . ?
C1 O1 C2 C3 -0.87(15) . . . . ?
C1 N1 C3 C13 179.37(13) . . . . ?
C1 N1 C3 C2 -0.85(16) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C13 C18 C17 C16 -0.7(2) . . . . ?
C6 C5 C4 C1 -174.27(13) . . . . ?
C4 C5 C6 O3 167.70(13) . . . . ?
C4 C5 C6 O2 -12.8(2) . . . . ?
C2 O1 C1 N1 0.35(16) . . . . ?
C2 O1 C1 C4 -176.58(13) . . . . ?
C2 C7 C12 C11 177.91(13) . . . . ?
C2 C7 C8 C9 -178.88(13) . . . . ?
C7 C2 C3 N1 -177.52(15) . . . . ?
C7 C2 C3 C13 2.2(3) . . . . ?
C7 C12 C11 C10 0.9(2) . . . . ?
C14 C13 C18 C17 0.9(2) . . . . ?
C14 C13 C3 N1 30.4(2) . . . . ?
C14 C13 C3 C2 -149.30(16) . . . . ?
C18 C13 C14 C15 -0.5(2) . . . . ?
C18 C13 C3 N1 -148.00(14) . . . . ?
C18 C13 C3 C2 32.3(2) . . . . ?
C18 C17 C16 C15 -0.1(3) . . . . ?
C12 C7 C8 C9 -0.9(2) . . . . ?
C12 C11 C10 C9 -0.7(2) . . . . ?
C3 N1 C1 O1 0.30(16) . . . . ?
C3 N1 C1 C4 177.06(14) . . . . ?
C3 C13 C14 C15 -178.96(14) . . . . ?
C3 C13 C18 C17 179.37(14) . . . . ?
C3 C2 C7 C12 32.8(2) . . . . ?
C3 C2 C7 C8 -149.24(17) . . . . ?
C17 C16 C15 C14 0.5(3) . . . . ?
C8 C7 C12 C11 -0.1(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C10 C9 C8 C7 1.1(2) . . . . ?
C22 C21 C20 C19 -1.8(2) . . . . ?
C21 C22 C23 N2 0.8(2) . . . . ?
C21 C21 C20 C19 178.02(16) 2_656 . . . ?
C21 C20 C19 N2 1.3(2) . . . . ?
C19 N2 C23 C22 -1.4(2) . . . . ?
C23 N2 C19 C20 0.3(2) . . . . ?
C23 C22 C21 C21 -179.02(16) . . . 2_656 ?
C23 C22 C21 C20 0.8(2) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_OXP-PIP
_database_code_depnum_ccdc_archive 'CCDC 1062960'
_audit_update_record             
;
2015-05-04 deposited with the CCDC.
2016-03-28 downloaded from the CCDC.
;
_audit_creation_date             2015-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            Oxaprozin-piperazine
_chemical_name_systematic        '1:0.5 Salt of Oxaprozin and piperazine'
_chemical_formula_moiety         'C18 H14 N O3, C2 H6 N'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38
_chemical_melting_point          477.83
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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'

_cell_length_a                   5.8155(12)
_cell_length_b                   7.3355(15)
_cell_length_c                   19.744(4)
_cell_angle_alpha                90.14(3)
_cell_angle_beta                 91.13(3)
_cell_angle_gamma                99.08(3)
_cell_volume                     831.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2752
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      30.8069
_cell_measurement_theta_min      2.0632
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12253
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.81
_diffrn_ambient_temperature      110.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             4762
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.1737
_diffrn_orient_matrix_UB_12      0.0082
_diffrn_orient_matrix_UB_13      0.0103
_diffrn_orient_matrix_UB_21      -0.0150
_diffrn_orient_matrix_UB_22      -0.0242
_diffrn_orient_matrix_UB_23      0.1351
_diffrn_orient_matrix_UB_31      0.0019
_diffrn_orient_matrix_UB_32      0.0497
_diffrn_orient_matrix_UB_33      0.0094
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3749
_reflns_number_total             4093
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      1.181
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.6843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C10(H10), C18(H18), C17(H17), C12(H12), C9(H9), C14(H14),
 C16(H16), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O2 O 0.0517(2) 1.24396(18) 0.43360(7) 0.0246(3) Uani 1 d . . .
O3 O -0.2662(2) 1.03754(18) 0.45283(7) 0.0259(3) Uani 1 d . . .
O1 O 0.1788(2) 0.88268(19) 0.22703(7) 0.0250(3) Uani 1 d . . .
N1 N 0.4218(3) 0.7572(2) 0.29373(8) 0.0223(3) Uani 1 d . . .
C3 C 0.4075(3) 0.6680(3) 0.23062(9) 0.0221(4) Uani 1 d . . .
C4 C 0.2359(3) 1.0123(3) 0.34188(10) 0.0229(4) Uani 1 d . . .
H4A H 0.2345 1.1350 0.3213 0.027 Uiso 1 calc . . R
H4B H 0.3623 1.0253 0.3767 0.027 Uiso 1 calc . . R
C6 C -0.0724(3) 1.0900(2) 0.42486(9) 0.0213(4) Uani 1 d . . .
C7 C 0.1939(3) 0.7356(3) 0.11749(10) 0.0221(4) Uani 1 d . . .
C13 C 0.5338(3) 0.5112(3) 0.22181(9) 0.0227(4) Uani 1 d . . .
C5 C 0.0024(3) 0.9499(3) 0.37597(10) 0.0244(4) Uani 1 d . . .
H5A H -0.1198 0.9208 0.3402 0.029 Uiso 1 calc . . R
H5B H 0.0121 0.8345 0.4010 0.029 Uiso 1 calc . . R
C1 C 0.2855(3) 0.8810(3) 0.28876(10) 0.0237(4) Uani 1 d . . .
C2 C 0.2609(3) 0.7473(3) 0.18930(10) 0.0225(4) Uani 1 d . . .
C11 C 0.2893(4) 0.6807(3) 0.00125(10) 0.0277(4) Uani 1 d . . .
H11 H 0.3930 0.6430 -0.0306 0.033 Uiso 1 calc . . R
C8 C -0.0143(3) 0.7899(3) 0.09470(10) 0.0253(4) Uani 1 d . . .
H8 H -0.1188 0.8273 0.1264 0.030 Uiso 1 calc . . R
C10 C 0.0829(4) 0.7350(3) -0.02115(10) 0.0288(4) Uani 1 d . . .
H10 H 0.0452 0.7352 -0.0682 0.035 Uiso 1 calc . . R
C18 C 0.4479(4) 0.3607(3) 0.17978(10) 0.0264(4) Uani 1 d . . .
H18 H 0.3067 0.3600 0.1547 0.032 Uiso 1 calc . . R
C17 C 0.5689(4) 0.2124(3) 0.17472(11) 0.0298(4) Uani 1 d . . .
H17 H 0.5118 0.1119 0.1454 0.036 Uiso 1 calc . . R
C12 C 0.3451(3) 0.6810(3) 0.06990(10) 0.0251(4) Uani 1 d . . .
H12 H 0.4871 0.6439 0.0847 0.030 Uiso 1 calc . . R
C9 C -0.0683(4) 0.7892(3) 0.02595(11) 0.0294(4) Uani 1 d . . .
H9 H -0.2100 0.8262 0.0109 0.035 Uiso 1 calc . . R
C14 C 0.7398(3) 0.5073(3) 0.25892(10) 0.0263(4) Uani 1 d . . .
H14 H 0.8002 0.6085 0.2876 0.032 Uiso 1 calc . . R
C16 C 0.7725(4) 0.2102(3) 0.21231(12) 0.0338(5) Uani 1 d . . .
H16 H 0.8535 0.1078 0.2091 0.041 Uiso 1 calc . . R
C15 C 0.8575(4) 0.3576(3) 0.25452(11) 0.0321(5) Uani 1 d . . .
H15 H 0.9965 0.3561 0.2805 0.039 Uiso 1 calc . . R
N2 N 0.5075(3) 0.3113(2) 0.48179(8) 0.0197(3) Uani 1 d . . .
C19 C 0.5828(3) 0.4631(2) 0.43375(9) 0.0228(4) Uani 1 d . . .
H19A H 0.5504 0.4179 0.3867 0.027 Uiso 1 calc . . R
H19B H 0.7528 0.5041 0.4391 0.027 Uiso 1 calc . . R
C20 C 0.5441(3) 0.3755(3) 0.55342(9) 0.0224(4) Uani 1 d . . .
H20A H 0.7127 0.4133 0.5629 0.027 Uiso 1 calc . . R
H20B H 0.4861 0.2730 0.5842 0.027 Uiso 1 calc . . R
H2A H 0.348(4) 0.269(3) 0.4734(11) 0.020(5) Uiso 1 d . . .
H2B H 0.600(5) 0.206(4) 0.4714(13) 0.041(7) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C6 1.250(2) . ?
O3 C6 1.269(2) . ?
O1 C1 1.358(2) . ?
O1 C2 1.389(2) . ?
N1 C3 1.401(2) . ?
N1 C1 1.299(3) . ?
C3 C13 1.471(3) . ?
C3 C2 1.364(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.532(3) . ?
C4 C1 1.485(2) . ?
C6 C5 1.527(2) . ?
C7 C2 1.462(3) . ?
C7 C8 1.399(3) . ?
C7 C12 1.399(3) . ?
C13 C18 1.401(3) . ?
C13 C14 1.396(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C10 1.388(3) . ?
C11 C12 1.387(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.392(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.390(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.387(3) . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.385(3) . ?
C15 H15 0.9500 . ?
N2 C19 1.483(2) . ?
N2 C20 1.490(2) . ?
N2 H2A 0.94(2) . ?
N2 H2B 1.03(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.514(3) 2_666 ?
C20 C19 1.514(3) 2_666 ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 105.40(15) . . ?
C1 N1 C3 105.70(16) . . ?
N1 C3 C13 118.47(17) . . ?
C2 C3 N1 108.46(16) . . ?
C2 C3 C13 132.99(17) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C1 C4 H4A 109.1 . . ?
C1 C4 H4B 109.1 . . ?
C1 C4 C5 112.58(16) . . ?
O2 C6 O3 125.13(17) . . ?
O2 C6 C5 120.13(17) . . ?
O3 C6 C5 114.72(16) . . ?
C8 C7 C2 120.80(17) . . ?
C12 C7 C2 120.14(17) . . ?
C12 C7 C8 118.93(18) . . ?
C18 C13 C3 122.01(18) . . ?
C14 C13 C3 119.23(17) . . ?
C14 C13 C18 118.69(18) . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
C6 C5 C4 115.04(16) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
O1 C1 C4 119.21(17) . . ?
N1 C1 O1 113.22(17) . . ?
N1 C1 C4 127.56(18) . . ?
O1 C2 C7 116.47(16) . . ?
C3 C2 O1 107.18(16) . . ?
C3 C2 C7 136.01(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C10 120.40(19) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.12(19) . . ?
C9 C8 H8 119.9 . . ?
C11 C10 H10 120.3 . . ?
C11 C10 C9 119.36(19) . . ?
C9 C10 H10 120.3 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.1(2) . . ?
C17 C18 H18 119.9 . . ?
C18 C17 H17 119.8 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.49(19) . . ?
C11 C12 H12 119.8 . . ?
C8 C9 C10 120.69(19) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.88(19) . . ?
C15 C16 H16 120.1 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C19 N2 C20 111.34(14) . . ?
C19 N2 H2A 107.7(13) . . ?
C19 N2 H2B 107.5(15) . . ?
C20 N2 H2A 109.5(13) . . ?
C20 N2 H2B 111.6(15) . . ?
H2A N2 H2B 109(2) . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 C20 110.58(15) . 2_666 ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.5 2_666 . ?
C20 C19 H19B 109.5 2_666 . ?
N2 C20 C19 110.47(15) . 2_666 ?
N2 C20 H20A 109.6 . . ?
N2 C20 H20B 109.6 . . ?
C19 C20 H20A 109.6 2_666 . ?
C19 C20 H20B 109.6 2_666 . ?
H20A C20 H20B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C6 C5 C4 1.4(3) . . . . ?
O3 C6 C5 C4 179.89(16) . . . . ?
N1 C3 C13 C18 146.34(18) . . . . ?
N1 C3 C13 C14 -30.4(3) . . . . ?
N1 C3 C2 O1 -1.5(2) . . . . ?
N1 C3 C2 C7 171.2(2) . . . . ?
C3 N1 C1 O1 0.2(2) . . . . ?
C3 N1 C1 C4 179.32(18) . . . . ?
C3 C13 C18 C17 -177.76(18) . . . . ?
C3 C13 C14 C15 176.77(18) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C13 C3 C2 O1 175.18(19) . . . . ?
C13 C3 C2 C7 -12.1(4) . . . . ?
C13 C18 C17 C16 1.4(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C5 C4 C1 O1 78.4(2) . . . . ?
C5 C4 C1 N1 -100.8(2) . . . . ?
C1 O1 C2 C3 1.6(2) . . . . ?
C1 O1 C2 C7 -172.81(16) . . . . ?
C1 N1 C3 C13 -176.39(17) . . . . ?
C1 N1 C3 C2 0.9(2) . . . . ?
C1 C4 C5 C6 -172.86(16) . . . . ?
C2 O1 C1 N1 -1.1(2) . . . . ?
C2 O1 C1 C4 179.68(16) . . . . ?
C2 C3 C13 C18 -30.1(3) . . . . ?
C2 C3 C13 C14 153.2(2) . . . . ?
C2 C7 C8 C9 175.86(18) . . . . ?
C2 C7 C12 C11 -175.96(18) . . . . ?
C11 C10 C9 C8 0.2(3) . . . . ?
C8 C7 C2 O1 -28.3(3) . . . . ?
C8 C7 C2 C3 159.4(2) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C10 C11 C12 C7 0.2(3) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
C18 C17 C16 C15 -0.8(3) . . . . ?
C17 C16 C15 C14 -0.3(3) . . . . ?
C12 C7 C2 O1 147.51(18) . . . . ?
C12 C7 C2 C3 -24.7(3) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
C12 C11 C10 C9 -0.2(3) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
C19 N2 C20 C19 56.7(2) . . . 2_666 ?
C20 N2 C19 C20 -56.8(2) . . . 2_666 ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_OXP
_database_code_depnum_ccdc_archive 'CCDC 1062961'
_audit_update_record             
;
2015-05-04 deposited with the CCDC.
2016-03-28 downloaded from the CCDC.
;

_vrf_DIFMX01_OXP                 
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: Absorption corrections were applied and all other other sources of
error were carefully examined. The fact that all the remaining atoms were
assigned accurately assuming the residual electron density as an additional
hydrogen atom would result in unrealistic model. Nearest atom to the highest
residual election density: C5, distance: 0.80 \%A.
;
_vrf_PLAT097_OXP                 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.81 eA-3  
RESPONSE: Multi-scan absorption correction was used for all the heavy atoms. The 
relatively high residual electron density peak is near the C5 atom and is not 
in a chemically sensible position. The maximum electron density peak of 
0.81 e\%A^-3^ was located 0.80 \%A from the C5 atom.
;

_audit_creation_date             2015-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            Oxaprozin
_chemical_name_systematic        Oxaprozin
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_chemical_melting_point          437.33
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   10.3129(5)
_cell_length_b                   7.6460(3)
_cell_length_c                   36.7642(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2899.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1232
_exptl_crystal_preparation       'Crystallization from 1,4-Dioxane'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,4-Dioxane'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            28497
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.97
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Agilent Supernova G8910B'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3558
_reflns_number_total             4042
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0720P)²+2.4480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1579
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C8(H8), C12(H12), C11(H11), C16(H16), C14(H14), C9(H9), C17(H17),
 C10(H10), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.43397(10) 0.91366(15) 0.39174(3) 0.0191(2) Uani 1 d . . .
O3 O 0.60776(13) 0.69947(19) 0.51386(3) 0.0305(3) Uani 1 d . . .
N1 N 0.25909(13) 0.87584(18) 0.42562(3) 0.0191(3) Uani 1 d . . .
O2 O 0.75569(14) 0.5925(2) 0.47541(4) 0.0404(4) Uani 1 d . . .
C18 C 0.02783(15) 1.0160(2) 0.35363(4) 0.0191(3) Uani 1 d . . .
H18 H 0.0836 1.0861 0.3391 0.023 Uiso 1 calc . . R
C2 C 0.32747(14) 0.92805(19) 0.36880(4) 0.0151(3) Uani 1 d . . .
C13 C 0.07980(14) 0.91084(19) 0.38121(4) 0.0159(3) Uani 1 d . . .
C7 C 0.35862(14) 0.95795(18) 0.33044(4) 0.0149(3) Uani 1 d . . .
C8 C 0.47375(14) 1.0457(2) 0.32147(4) 0.0180(3) Uani 1 d . . .
H8 H 0.5292 1.0871 0.3402 0.022 Uiso 1 calc . . R
C3 C 0.21890(14) 0.90630(19) 0.38960(4) 0.0159(3) Uani 1 d . . .
C1 C 0.38496(15) 0.8832(2) 0.42523(4) 0.0198(3) Uani 1 d . . .
C12 C 0.27847(14) 0.8968(2) 0.30244(4) 0.0176(3) Uani 1 d . . .
H12 H 0.2008 0.8359 0.3082 0.021 Uiso 1 calc . . R
C11 C 0.31223(16) 0.9249(2) 0.26628(4) 0.0228(3) Uani 1 d . . .
H11 H 0.2569 0.8844 0.2474 0.027 Uiso 1 calc . . R
C16 C -0.18802(16) 0.9151(3) 0.36831(5) 0.0280(4) Uani 1 d . . .
H16 H -0.2787 0.9157 0.3637 0.034 Uiso 1 calc . . R
C14 C -0.00492(15) 0.8107(2) 0.40245(4) 0.0193(3) Uani 1 d . . .
H14 H 0.0288 0.7409 0.4216 0.023 Uiso 1 calc . . R
C9 C 0.50696(16) 1.0720(2) 0.28531(4) 0.0236(3) Uani 1 d . . .
H9 H 0.5850 1.1316 0.2794 0.028 Uiso 1 calc . . R
C6 C 0.65091(17) 0.6575(2) 0.48109(4) 0.0255(3) Uani 1 d . . .
C17 C -0.10511(16) 1.0180(2) 0.34736(5) 0.0251(4) Uani 1 d . . .
H17 H -0.1397 1.0901 0.3287 0.030 Uiso 1 calc . . R
C10 C 0.42665(17) 1.0118(2) 0.25763(4) 0.0256(4) Uani 1 d . . .
H10 H 0.4498 1.0300 0.2329 0.031 Uiso 1 calc . . R
C15 C -0.13755(16) 0.8118(2) 0.39591(5) 0.0252(4) Uani 1 d . . .
H15 H -0.1937 0.7418 0.4103 0.030 Uiso 1 calc . . R
C4 C 0.47785(17) 0.8612(2) 0.45587(4) 0.0258(4) Uani 1 d . . .
H4A H 0.4300 0.8615 0.4792 0.031 Uiso 1 calc . . R
H4B H 0.5396 0.9603 0.4561 0.031 Uiso 1 calc . . R
C5 C 0.55178(19) 0.6908(3) 0.45196(5) 0.0333(4) Uani 1 d . . .
H5A H 0.4888 0.5931 0.4520 0.040 Uiso 1 calc . . R
H5B H 0.5961 0.6905 0.4281 0.040 Uiso 1 calc . . R
H3 H 0.664(4) 0.650(6) 0.5328(12) 0.118(15) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3891(17) . ?
O1 C1 1.3511(18) . ?
O3 C6 1.324(2) . ?
O3 H3 0.98(5) . ?
N1 C3 1.4069(18) . ?
N1 C1 1.299(2) . ?
O2 C6 1.208(2) . ?
C18 H18 0.9500 . ?
C18 C13 1.401(2) . ?
C18 C17 1.390(2) . ?
C2 C7 1.464(2) . ?
C2 C3 1.366(2) . ?
C13 C3 1.468(2) . ?
C13 C14 1.400(2) . ?
C7 C8 1.403(2) . ?
C7 C12 1.401(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(2) . ?
C1 C4 1.488(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.391(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.391(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(3) . ?
C16 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(2) . ?
C6 C5 1.502(2) . ?
C17 H17 0.9500 . ?
C10 H10 0.9500 . ?
C15 H15 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.516(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 105.73(12) . . ?
C6 O3 H3 111(3) . . ?
C1 N1 C3 106.06(12) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C13 120.26(15) . . ?
O1 C2 C7 115.06(12) . . ?
C3 C2 O1 107.36(12) . . ?
C3 C2 C7 137.57(13) . . ?
C18 C13 C3 122.67(13) . . ?
C14 C13 C18 118.62(14) . . ?
C14 C13 C3 118.68(14) . . ?
C8 C7 C2 119.14(13) . . ?
C12 C7 C2 121.76(13) . . ?
C12 C7 C8 119.08(13) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.25(15) . . ?
C9 C8 H8 119.9 . . ?
N1 C3 C13 119.32(13) . . ?
C2 C3 N1 107.80(13) . . ?
C2 C3 C13 132.88(14) . . ?
O1 C1 C4 117.93(14) . . ?
N1 C1 O1 113.04(13) . . ?
N1 C1 C4 129.02(14) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.22(14) . . ?
C11 C12 H12 119.9 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C10 120.31(15) . . ?
C10 C11 H11 119.8 . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.69(15) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 120.98(15) . . ?
C15 C14 H14 119.5 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.40(15) . . ?
C10 C9 H9 119.8 . . ?
O3 C6 C5 112.27(15) . . ?
O2 C6 O3 123.93(16) . . ?
O2 C6 C5 123.72(16) . . ?
C18 C17 C16 120.45(16) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C11 C10 H10 120.1 . . ?
C9 C10 C11 119.73(15) . . ?
C9 C10 H10 120.1 . . ?
C16 C15 C14 119.98(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C1 C4 H4A 109.6 . . ?
C1 C4 H4B 109.6 . . ?
C1 C4 C5 110.41(14) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C6 C5 C4 114.85(15) . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C7 C8 -28.61(19) . . . . ?
O1 C2 C7 C12 149.47(14) . . . . ?
O1 C2 C3 N1 -0.80(16) . . . . ?
O1 C2 C3 C13 178.59(15) . . . . ?
O1 C1 C4 C5 -69.5(2) . . . . ?
O3 C6 C5 C4 42.1(2) . . . . ?
N1 C1 C4 C5 109.8(2) . . . . ?
O2 C6 C5 C4 -141.0(2) . . . . ?
C18 C13 C3 N1 148.36(14) . . . . ?
C18 C13 C3 C2 -31.0(2) . . . . ?
C18 C13 C14 C15 1.5(2) . . . . ?
C2 O1 C1 N1 0.42(17) . . . . ?
C2 O1 C1 C4 179.85(14) . . . . ?
C2 C7 C8 C9 178.50(14) . . . . ?
C2 C7 C12 C11 -178.85(14) . . . . ?
C13 C18 C17 C16 -0.3(2) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C7 C2 C3 N1 177.88(17) . . . . ?
C7 C2 C3 C13 -2.7(3) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C7 C12 C11 C10 0.8(2) . . . . ?
C8 C7 C12 C11 -0.8(2) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C3 N1 C1 O1 -0.91(18) . . . . ?
C3 N1 C1 C4 179.74(16) . . . . ?
C3 C2 C7 C8 152.78(18) . . . . ?
C3 C2 C7 C12 -29.1(3) . . . . ?
C3 C13 C14 C15 179.30(14) . . . . ?
C1 O1 C2 C7 -178.75(13) . . . . ?
C1 O1 C2 C3 0.27(16) . . . . ?
C1 N1 C3 C2 1.04(17) . . . . ?
C1 N1 C3 C13 -178.44(13) . . . . ?
C1 C4 C5 C6 178.58(16) . . . . ?
C12 C7 C8 C9 0.4(2) . . . . ?
C12 C11 C10 C9 -0.5(3) . . . . ?
C14 C13 C3 N1 -29.4(2) . . . . ?
C14 C13 C3 C2 151.30(16) . . . . ?
C17 C18 C13 C3 -178.60(14) . . . . ?
C17 C18 C13 C14 -0.9(2) . . . . ?
C17 C16 C15 C14 -0.3(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'Glass fiber'
