# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_mefenamicaicdBPE
_database_code_depnum_ccdc_archive 'CCDC 1864913'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_mefenamicaicdBPE    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report
RESPONSE: These reflections were missed using only omega scans during the
          data collection.
;
# end Validation Reply Form

_audit_creation_date             2018-02-12T16:41:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8199(14)
_cell_length_b                   8.6152(15)
_cell_length_c                   12.900(2)
_cell_angle_alpha                98.216(2)
_cell_angle_beta                 99.515(2)
_cell_angle_gamma                90.024(2)
_cell_volume                     848.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3310
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      26.96

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.065
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             352

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6845
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.995

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_number            9598
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.618
_diffrn_reflns_theta_max         27.071
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_number_total             3684
_reflns_number_gt                2901
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The hydrogen atom (H1A) bound to N1 was restrainted with an AFIX 44 command. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.2761P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3684
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.87448(13) -0.20288(11) 0.09389(8) 0.0232(2) Uani 1 d . .
H1 H 0.8295 -0.2934 0.0774 0.035 Uiso 1 calc . .
O2 O 0.72577(14) -0.19910(12) 0.22778(8) 0.0271(3) Uani 1 d . .
N1 N 0.76467(16) 0.05139(15) 0.37823(9) 0.0218(3) Uani 1 d . .
H1A H 0.7399(6) -0.042(2) 0.3647(3) 0.026 Uiso 1 d . .
N2 N 0.75358(15) 0.50490(13) 0.04220(9) 0.0199(3) Uani 1 d . .
C1 C 0.89080(17) 0.02924(15) 0.21647(10) 0.0172(3) Uani 1 d . .
C2 C 0.85497(17) 0.11718(16) 0.31190(11) 0.0181(3) Uani 1 d . .
C3 C 0.91718(18) 0.27388(16) 0.33773(11) 0.0211(3) Uani 1 d . .
H3 H 0.8937 0.3353 0.4008 0.025 Uiso 1 calc . .
C4 C 1.01115(19) 0.33906(17) 0.27321(12) 0.0231(3) Uani 1 d . .
H4 H 1.0503 0.4453 0.2919 0.028 Uiso 1 calc . .
C5 C 1.05015(19) 0.25220(17) 0.18080(11) 0.0229(3) Uani 1 d . .
H5 H 1.1173 0.2976 0.1374 0.027 Uiso 1 calc . .
C6 C 0.98943(18) 0.09908(16) 0.15358(11) 0.0200(3) Uani 1 d . .
H6 H 1.0152 0.0394 0.0905 0.024 Uiso 1 calc . .
C7 C 0.82251(18) -0.13314(16) 0.18112(11) 0.0187(3) Uani 1 d . .
C8 C 0.71227(18) 0.13960(16) 0.46997(11) 0.0197(3) Uani 1 d . .
C9 C 0.54542(18) 0.19984(16) 0.46361(11) 0.0207(3) Uani 1 d . .
C10 C 0.49683(19) 0.28432(16) 0.55545(11) 0.0213(3) Uani 1 d . .
C11 C 0.61580(19) 0.30588(17) 0.64958(11) 0.0234(3) Uani 1 d . .
H11 H 0.5829 0.3623 0.7118 0.028 Uiso 1 calc . .
C12 C 0.78125(19) 0.24669(17) 0.65450(11) 0.0247(3) Uani 1 d . .
H12 H 0.8611 0.2635 0.7193 0.03 Uiso 1 calc . .
C13 C 0.82967(19) 0.16291(17) 0.56453(11) 0.0230(3) Uani 1 d . .
H13 H 0.9427 0.1215 0.5674 0.028 Uiso 1 calc . .
C14 C 0.4201(2) 0.1780(2) 0.36041(12) 0.0294(4) Uani 1 d . .
H14A H 0.3862 0.2808 0.3408 0.044 Uiso 1 calc . .
H14B H 0.3169 0.1194 0.3686 0.044 Uiso 1 calc . .
H14C H 0.4756 0.1195 0.3046 0.044 Uiso 1 calc . .
C15 C 0.3194(2) 0.3540(2) 0.55150(13) 0.0298(4) Uani 1 d . .
H15A H 0.3069 0.4331 0.5034 0.045 Uiso 1 calc . .
H15B H 0.3055 0.4031 0.6229 0.045 Uiso 1 calc . .
H15C H 0.2306 0.271 0.5257 0.045 Uiso 1 calc . .
C16 C 0.78319(19) 0.40572(16) -0.04247(11) 0.0215(3) Uani 1 d . .
H16 H 0.8537 0.4415 -0.088 0.026 Uiso 1 calc . .
C17 C 0.71630(19) 0.25407(16) -0.06692(11) 0.0221(3) Uani 1 d . .
H17 H 0.7403 0.1883 -0.1282 0.026 Uiso 1 calc . .
C18 C 0.61420(18) 0.19834(16) -0.00163(11) 0.0208(3) Uani 1 d . .
C19 C 0.58278(19) 0.30141(17) 0.08683(12) 0.0234(3) Uani 1 d . .
H19 H 0.5128 0.2686 0.1337 0.028 Uiso 1 calc . .
C20 C 0.65467(18) 0.45175(17) 0.10548(11) 0.0219(3) Uani 1 d . .
H20 H 0.6327 0.5204 0.1661 0.026 Uiso 1 calc . .
C21 C 0.54806(18) 0.03498(16) -0.02773(11) 0.0230(3) Uani 1 d . .
H21 H 0.5771 -0.0252 -0.0898 0.028 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C7 1.3231(16) . ?
O1 H1 0.84 . ?
O2 C7 1.2269(16) . ?
N1 C2 1.3748(18) . ?
N1 C8 1.4316(17) . ?
N1 H1A 0.815(17) . ?
N2 C20 1.3377(18) . ?
N2 C16 1.3392(18) . ?
C1 C6 1.4004(19) . ?
C1 C2 1.4198(18) . ?
C1 C7 1.4788(19) . ?
C2 C3 1.4097(19) . ?
C3 C4 1.372(2) . ?
C3 H3 0.95 . ?
C4 C5 1.393(2) . ?
C4 H4 0.95 . ?
C5 C6 1.379(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C8 C13 1.389(2) . ?
C8 C9 1.399(2) . ?
C9 C10 1.4072(19) . ?
C9 C14 1.505(2) . ?
C10 C11 1.392(2) . ?
C10 C15 1.508(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.95 . ?
C12 C13 1.385(2) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 C17 1.381(2) . ?
C16 H16 0.95 . ?
C17 C18 1.384(2) . ?
C17 H17 0.95 . ?
C18 C19 1.398(2) . ?
C18 C21 1.472(2) . ?
C19 C20 1.385(2) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 C21 1.319(3) 2_655 ?
C21 H21 0.95 . ?

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
C7 O1 H1 109.5 . . ?
C2 N1 C8 122.94(12) . . ?
C2 N1 H1A 118.5(3) . . ?
C8 N1 H1A 118.6(3) . . ?
C20 N2 C16 117.32(12) . . ?
C6 C1 C2 119.26(12) . . ?
C6 C1 C7 119.49(12) . . ?
C2 C1 C7 121.23(12) . . ?
N1 C2 C3 120.76(12) . . ?
N1 C2 C1 121.24(12) . . ?
C3 C2 C1 117.99(12) . . ?
C4 C3 C2 121.05(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.18(13) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.73(13) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 121.75(13) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
O2 C7 O1 122.17(12) . . ?
O2 C7 C1 123.58(12) . . ?
O1 C7 C1 114.26(12) . . ?
C13 C8 C9 121.19(13) . . ?
C13 C8 N1 118.73(12) . . ?
C9 C8 N1 120.07(13) . . ?
C8 C9 C10 118.79(13) . . ?
C8 C9 C14 121.07(13) . . ?
C10 C9 C14 120.13(13) . . ?
C11 C10 C9 119.24(13) . . ?
C11 C10 C15 120.27(13) . . ?
C9 C10 C15 120.48(13) . . ?
C12 C11 C10 121.35(13) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 119.71(13) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 119.72(13) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 123.28(13) . . ?
N2 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
C16 C17 C18 119.65(13) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 117.31(13) . . ?
C17 C18 C21 118.70(13) . . ?
C19 C18 C21 123.99(13) . . ?
C20 C19 C18 119.34(13) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
N2 C20 C19 123.10(13) . . ?
N2 C20 H20 118.4 . . ?
C19 C20 H20 118.4 . . ?
C21 C21 C18 125.56(17) 2_655 . ?
C21 C21 H21 117.2 2_655 . ?
C18 C21 H21 117.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.815(17) 2.053(10) 2.6690(16) 132.1(7) .
O1 H1 N2 0.84 1.81 2.6432(16) 174.5 1_545

_chemical_name_systematic        
'co-crystal of mefenamic acid and 1,2-Bis(4-pyridyl)ethylene'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_mefenamicacidBPP
_database_code_depnum_ccdc_archive 'CCDC 1864916'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT906_mefenamicacidBPP    
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.861 Check 
RESPONSE: The variance was related to the strongest reflections.  Further
          examination did reveal that certain reflections had shoulder peaks
          that might not have been properly integrated by SAINT, resulting in
          this variance alert.  Attempts were made to integrate the data with
          different box sizes, both fixed and varied, but to no imporvement.
;
_vrf_PLAT911_hut18_25            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         12 Report
RESPONSE: These reflections were not collected using omega only scans. 
;
# end Validation Reply Form

_audit_creation_date             2018-03-09T09:18:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C28 H29 N3 O2'
_chemical_formula_weight         439.54

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.503(3)
_cell_length_b                   7.836(3)
_cell_length_c                   20.382(7)
_cell_angle_alpha                88.77(9)
_cell_angle_beta                 85.38(5)
_cell_angle_gamma                79.99(5)
_cell_volume                     1176.1(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1452
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      23.76

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       chip
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             468

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6794
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.998

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_number            4245
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.005
_diffrn_reflns_theta_max         25.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_number_total             4245
_reflns_number_gt                2845
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component non-merohedral twin. The final BASF value was 0.4103.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.1979P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4245
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.6752(2) 0.7589(2) 0.46599(8) 0.0233(4) Uani 1 d . .
H1A H 0.7141 0.6656 0.4852 0.035 Uiso 1 calc . .
O2 O 0.6400(2) 0.5763(2) 0.38660(8) 0.0265(4) Uani 1 d . .
N1 N 0.5543(3) 0.7101(3) 0.26838(9) 0.0239(5) Uani 1 d . .
H1B H 0.6029 0.6165 0.2895 0.029 Uiso 1 calc . .
N2 N 0.7925(3) 0.4722(3) 0.53214(9) 0.0225(5) Uani 1 d . .
N3 N 1.0962(3) -0.1978(3) 0.94419(10) 0.0326(6) Uani 1 d . .
C1 C 0.5478(3) 0.8695(3) 0.29787(12) 0.0192(6) Uani 1 d . .
C2 C 0.5829(3) 0.8821(3) 0.36480(11) 0.0179(5) Uani 1 d . .
C3 C 0.5689(3) 1.0466(3) 0.39274(12) 0.0215(6) Uani 1 d . .
H3 H 0.5892 1.0542 0.4379 0.026 Uiso 1 calc . .
C4 C 0.5268(3) 1.1978(3) 0.35681(12) 0.0241(6) Uani 1 d . .
H4 H 0.5184 1.3078 0.3767 0.029 Uiso 1 calc . .
C5 C 0.4969(3) 1.1847(3) 0.29068(12) 0.0224(6) Uani 1 d . .
H5 H 0.471 1.2871 0.2649 0.027 Uiso 1 calc . .
C6 C 0.5042(3) 1.0245(3) 0.26180(12) 0.0212(6) Uani 1 d . .
H6 H 0.4794 1.0193 0.217 0.025 Uiso 1 calc . .
C7 C 0.6342(3) 0.7252(3) 0.40615(11) 0.0189(5) Uani 1 d . .
C8 C 0.4872(3) 0.6878(3) 0.20572(12) 0.0215(6) Uani 1 d . .
C9 C 0.5769(3) 0.7356(3) 0.14704(12) 0.0224(6) Uani 1 d . .
C10 C 0.4996(4) 0.7161(3) 0.08724(12) 0.0250(6) Uani 1 d . .
C11 C 0.3433(4) 0.6444(3) 0.08749(13) 0.0273(6) Uani 1 d . .
H11 H 0.2917 0.6331 0.0471 0.033 Uiso 1 calc . .
C12 C 0.2605(4) 0.5889(3) 0.14518(13) 0.0279(6) Uani 1 d . .
H12 H 0.1566 0.5352 0.1442 0.034 Uiso 1 calc . .
C13 C 0.3313(3) 0.6127(3) 0.20470(12) 0.0224(6) Uani 1 d . .
H13 H 0.2737 0.5778 0.2447 0.027 Uiso 1 calc . .
C14 C 0.7537(4) 0.8014(4) 0.14694(13) 0.0317(7) Uani 1 d . .
H14A H 0.8393 0.744 0.112 0.048 Uiso 1 calc . .
H14B H 0.8044 0.7762 0.1896 0.048 Uiso 1 calc . .
H14C H 0.7327 0.9269 0.1391 0.048 Uiso 1 calc . .
C15 C 0.5928(4) 0.7680(4) 0.02303(13) 0.0387(7) Uani 1 d . .
H15A H 0.5137 0.764 -0.0127 0.058 Uiso 1 calc . .
H15B H 0.7072 0.6877 0.0136 0.058 Uiso 1 calc . .
H15C H 0.6178 0.886 0.0267 0.058 Uiso 1 calc . .
C16 C 0.8687(3) 0.4643(3) 0.59010(12) 0.0235(6) Uani 1 d . .
H16 H 0.8894 0.5691 0.6083 0.028 Uiso 1 calc . .
C17 C 0.9183(3) 0.3108(3) 0.62442(12) 0.0221(6) Uani 1 d . .
H17 H 0.9713 0.3122 0.6652 0.027 Uiso 1 calc . .
C18 C 0.8902(3) 0.1541(3) 0.59896(11) 0.0187(5) Uani 1 d . .
C19 C 0.8149(3) 0.1625(3) 0.53825(12) 0.0228(6) Uani 1 d . .
H19 H 0.7953 0.0594 0.5184 0.027 Uiso 1 calc . .
C20 C 0.7687(3) 0.3202(3) 0.50705(12) 0.0228(6) Uani 1 d . .
H20 H 0.7177 0.322 0.4658 0.027 Uiso 1 calc . .
C21 C 0.9336(3) -0.0190(3) 0.63346(11) 0.0221(6) Uani 1 d . .
H21A H 1.0407 -0.0881 0.6091 0.026 Uiso 1 calc . .
H21B H 0.8302 -0.0809 0.6305 0.026 Uiso 1 calc . .
C22 C 0.9725(3) -0.0145(3) 0.70576(11) 0.0211(6) Uani 1 d . .
H22A H 0.8738 0.0661 0.7298 0.025 Uiso 1 calc . .
H22B H 1.0873 0.0296 0.709 0.025 Uiso 1 calc . .
C23 C 0.9877(3) -0.1944(3) 0.73779(11) 0.0219(6) Uani 1 d . .
H23A H 0.8738 -0.239 0.7332 0.026 Uiso 1 calc . .
H23B H 1.0877 -0.2738 0.7138 0.026 Uiso 1 calc . .
C24 C 1.0226(3) -0.1962(3) 0.81001(12) 0.0199(6) Uani 1 d . .
C25 C 1.1642(4) -0.3120(3) 0.83440(12) 0.0267(6) Uani 1 d . .
H25 H 1.2395 -0.3936 0.8059 0.032 Uiso 1 calc . .
C26 C 1.1952(4) -0.3081(4) 0.90039(13) 0.0343(7) Uani 1 d . .
H26 H 1.293 -0.3889 0.9156 0.041 Uiso 1 calc . .
C27 C 0.9583(4) -0.0870(3) 0.92061(12) 0.0259(6) Uani 1 d . .
H27 H 0.8849 -0.0073 0.9503 0.031 Uiso 1 calc . .
C28 C 0.9169(3) -0.0821(3) 0.85541(11) 0.0228(6) Uani 1 d . .
H28 H 0.817 -0.0014 0.8416 0.027 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C7 1.325(3) . ?
O1 H1A 0.84 . ?
O2 C7 1.234(3) . ?
N1 C1 1.390(3) . ?
N1 C8 1.435(3) . ?
N1 H1B 0.88 . ?
N2 C16 1.349(3) . ?
N2 C20 1.351(3) . ?
N3 C26 1.342(4) . ?
N3 C27 1.344(3) . ?
C1 C6 1.409(3) . ?
C1 C2 1.419(3) . ?
C2 C3 1.404(3) . ?
C2 C7 1.487(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.95 . ?
C4 C5 1.393(3) . ?
C4 H4 0.95 . ?
C5 C6 1.388(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C8 C13 1.399(3) . ?
C8 C9 1.401(4) . ?
C9 C10 1.413(4) . ?
C9 C14 1.505(4) . ?
C10 C11 1.385(4) . ?
C10 C15 1.515(4) . ?
C11 C12 1.383(4) . ?
C11 H11 0.95 . ?
C12 C13 1.392(3) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 C17 1.387(4) . ?
C16 H16 0.95 . ?
C17 C18 1.399(3) . ?
C17 H17 0.95 . ?
C18 C19 1.397(3) . ?
C18 C21 1.511(4) . ?
C19 C20 1.380(4) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 C22 1.528(3) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C23 1.530(4) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C24 1.515(3) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.389(3) . ?
C24 C28 1.398(4) . ?
C25 C26 1.385(4) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
C27 C28 1.387(3) . ?
C27 H27 0.95 . ?
C28 H28 0.95 . ?

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
C7 O1 H1A 109.5 . . ?
C1 N1 C8 124.3(2) . . ?
C1 N1 H1B 117.8 . . ?
C8 N1 H1B 117.8 . . ?
C16 N2 C20 116.7(2) . . ?
C26 N3 C27 115.8(2) . . ?
N1 C1 C6 120.5(2) . . ?
N1 C1 C2 121.6(2) . . ?
C6 C1 C2 118.0(2) . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 C7 119.1(2) . . ?
C1 C2 C7 121.6(2) . . ?
C4 C3 C2 122.3(2) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 121.1(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O2 C7 O1 122.6(2) . . ?
O2 C7 C2 123.3(2) . . ?
O1 C7 C2 114.1(2) . . ?
C13 C8 C9 120.7(2) . . ?
C13 C8 N1 118.0(2) . . ?
C9 C8 N1 121.3(2) . . ?
C8 C9 C10 118.3(2) . . ?
C8 C9 C14 121.3(2) . . ?
C10 C9 C14 120.4(2) . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 C15 120.5(2) . . ?
C9 C10 C15 119.5(2) . . ?
C12 C11 C10 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C8 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 123.3(2) . . ?
N2 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17 120 . . ?
C18 C17 H17 120 . . ?
C19 C18 C17 116.6(2) . . ?
C19 C18 C21 119.3(2) . . ?
C17 C18 C21 124.0(2) . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
N2 C20 C19 123.4(2) . . ?
N2 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?
C18 C21 C22 116.5(2) . . ?
C18 C21 H21A 108.2 . . ?
C22 C21 H21A 108.2 . . ?
C18 C21 H21B 108.2 . . ?
C22 C21 H21B 108.2 . . ?
H21A C21 H21B 107.3 . . ?
C21 C22 C23 111.6(2) . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108 . . ?
C24 C23 C22 113.6(2) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C28 116.4(2) . . ?
C25 C24 C23 121.1(2) . . ?
C28 C24 C23 122.5(2) . . ?
C26 C25 C24 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
N3 C26 C25 124.3(3) . . ?
N3 C26 H26 117.9 . . ?
C25 C26 H26 117.9 . . ?
N3 C27 C28 123.8(2) . . ?
N3 C27 H27 118.1 . . ?
C28 C27 H27 118.1 . . ?
C27 C28 C24 119.9(2) . . ?
C27 C28 H28 120.1 . . ?
C24 C28 H28 120.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N2 0.84 1.81 2.649(3) 175.9 .
N1 H1B O2 0.88 2.03 2.688(3) 130.6 .


# END of CIF
_chemical_name_systematic        
'co-crystal of mefenamic acid and 1,3-Bis(4-pyridyl)propane'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_naproxenBPEth
_database_code_depnum_ccdc_archive 'CCDC 1864925'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_STRVA01_naproxenBPEth       
;
PROBLEM: Flack test results are meaningless.
RESPONSE: ...
;
_vrf_PLAT089_hut18_28            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       7.20 Note  
RESPONSE: This is due to modeling the positional disorder within the structure.
;
_vrf_PLAT340_hut18_28            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00414 Ang.  
RESPONSE: The crystals were weak diffractors at high angles.
;
_vrf_PLAT911_hut18_28            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
RESPONSE: These reflections were not collected using only omega scans.
;
# end Validation Reply Form

_audit_creation_date             2018-03-14T15:11:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C40 H40 N2 O6'
_chemical_formula_weight         644.74
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   38.014(16)
_cell_length_b                   5.787(3)
_cell_length_c                   15.566(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.646(6)
_cell_angle_gamma                90
_cell_volume                     3418(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    4039
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.88

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             1368

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6546
_shelx_estimated_absorpt_T_min   0.96
_shelx_estimated_absorpt_T_max   0.996

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_number            17520
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.073
_diffrn_reflns_theta_max         25.414
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_number_total             6219
_reflns_number_gt                4854
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Carbon atoms C37 < C40 were disorder over two sites (A and B) and were
 allowed to free refine their occupancies to a total value of one. The 
 occupancies for the A and B sites were 0.72 and 0.28, respectively. To
 help restrain the minor sites DFIX, SIMU, and DELU restraints were 
 applied.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6219
_refine_ls_number_parameters     479
_refine_ls_number_restraints     557
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.39682(6) 0.3261(4) 0.87914(14) 0.0401(6) Uani 1 d . .
H1 H 0.4097 0.3052 0.838 0.06 Uiso 1 calc . .
O2 O 0.42249(6) 0.6733(4) 0.88196(17) 0.0556(7) Uani 1 d . .
O3 O 0.17481(5) 0.7623(4) 0.83138(13) 0.0369(5) Uani 1 d . .
O4 O 0.60145(6) 0.4319(4) 0.61669(14) 0.0419(6) Uani 1 d . .
H4A H 0.5878 0.4119 0.6564 0.063 Uiso 1 calc . .
O5 O 0.56801(6) 0.7438(5) 0.59258(17) 0.0620(8) Uani 1 d . .
O6 O 0.82198(5) 0.7371(4) 0.66741(12) 0.0343(5) Uani 1 d . .
N1 N 0.43516(6) 0.2489(5) 0.74503(16) 0.0367(6) Uani 1 d . .
C1 C 0.40141(8) 0.5386(6) 0.9093(2) 0.0348(7) Uani 1 d . .
C2 C 0.37663(7) 0.5947(6) 0.97889(19) 0.0339(8) Uani 1 d . .
H2 H 0.374 0.4525 1.0145 0.041 Uiso 1 calc . .
C3 C 0.34060(7) 0.6559(5) 0.93740(18) 0.0266(7) Uani 1 d . .
C4 C 0.33518(8) 0.8628(5) 0.88945(19) 0.0306(7) Uani 1 d . .
H4 H 0.3546 0.9621 0.8817 0.037 Uiso 1 calc . .
C5 C 0.30246(7) 0.9227(5) 0.85412(18) 0.0280(7) Uani 1 d . .
H5 H 0.2998 1.0609 0.8214 0.034 Uiso 1 calc . .
C6 C 0.27249(7) 0.7820(5) 0.86557(17) 0.0242(6) Uani 1 d . .
C7 C 0.23770(7) 0.8488(5) 0.83523(18) 0.0282(7) Uani 1 d . .
H7 H 0.2341 0.9867 0.8028 0.034 Uiso 1 calc . .
C8 C 0.20964(7) 0.7131(5) 0.85318(18) 0.0286(7) Uani 1 d . .
C9 C 0.21473(8) 0.5023(5) 0.89845(18) 0.0305(7) Uani 1 d . .
H9 H 0.195 0.4096 0.9102 0.037 Uiso 1 calc . .
C10 C 0.24788(7) 0.4317(5) 0.92528(17) 0.0279(7) Uani 1 d . .
H10 H 0.251 0.2869 0.9535 0.033 Uiso 1 calc . .
C11 C 0.27784(7) 0.5719(5) 0.91166(17) 0.0242(7) Uani 1 d . .
C12 C 0.31198(7) 0.5144(5) 0.94673(17) 0.0268(7) Uani 1 d . .
H12 H 0.3153 0.3737 0.9777 0.032 Uiso 1 calc . .
C13 C 0.39171(9) 0.7863(7) 1.0383(2) 0.0499(10) Uani 1 d . .
H13A H 0.3962 0.9241 1.0041 0.075 Uiso 1 calc . .
H13B H 0.4138 0.7335 1.0677 0.075 Uiso 1 calc . .
H13C H 0.3748 0.8238 1.081 0.075 Uiso 1 calc . .
C14 C 0.16716(8) 0.9724(6) 0.7859(2) 0.0429(9) Uani 1 d . .
H14A H 0.1781 0.9689 0.7306 0.064 Uiso 1 calc . .
H14B H 0.1765 1.1033 0.8202 0.064 Uiso 1 calc . .
H14C H 0.1416 0.9893 0.7758 0.064 Uiso 1 calc . .
C15 C 0.45558(8) 0.0634(6) 0.7364(2) 0.0391(8) Uani 1 d . .
H15 H 0.4536 -0.0616 0.7754 0.047 Uiso 1 calc . .
C16 C 0.47951(8) 0.0448(6) 0.67327(19) 0.0370(8) Uani 1 d . .
H16 H 0.4937 -0.0897 0.6702 0.044 Uiso 1 calc . .
C17 C 0.48277(7) 0.2226(6) 0.61447(19) 0.0304(7) Uani 1 d . .
C18 C 0.46106(7) 0.4122(6) 0.6223(2) 0.0367(8) Uani 1 d . .
H18 H 0.462 0.5372 0.5829 0.044 Uiso 1 calc . .
C19 C 0.43803(8) 0.4191(6) 0.6876(2) 0.0405(8) Uani 1 d . .
H19 H 0.4235 0.5515 0.6919 0.049 Uiso 1 calc . .
C20 C 0.50900(8) 0.2124(6) 0.54558(18) 0.0373(8) Uani 1 d . .
H20A H 0.5234 0.0706 0.5536 0.045 Uiso 1 calc . .
H20B H 0.525 0.3469 0.5519 0.045 Uiso 1 calc . .
C21 C 0.59368(8) 0.6288(6) 0.5770(2) 0.0350(8) Uani 1 d . .
C22 C 0.61954(7) 0.6909(6) 0.51079(19) 0.0323(7) Uani 1 d . .
H22 H 0.6209 0.5568 0.4706 0.039 Uiso 1 calc . .
C23 C 0.65609(7) 0.7250(5) 0.55514(18) 0.0272(7) Uani 1 d . .
C24 C 0.68265(7) 0.5677(5) 0.54551(18) 0.0262(7) Uani 1 d . .
H24 H 0.6777 0.431 0.5132 0.031 Uiso 1 calc . .
C25 C 0.71741(7) 0.6042(5) 0.58271(17) 0.0234(6) Uani 1 d . .
C26 C 0.74535(7) 0.4484(5) 0.57029(17) 0.0286(7) Uani 1 d . .
H26 H 0.7405 0.3066 0.5411 0.034 Uiso 1 calc . .
C27 C 0.77913(7) 0.4985(5) 0.59949(17) 0.0285(7) Uani 1 d . .
H27 H 0.7976 0.3935 0.5892 0.034 Uiso 1 calc . .
C28 C 0.78671(7) 0.7064(5) 0.64504(18) 0.0264(7) Uani 1 d . .
C29 C 0.76018(7) 0.8562(5) 0.66246(18) 0.0252(7) Uani 1 d . .
H29 H 0.7653 0.9914 0.6955 0.03 Uiso 1 calc . .
C30 C 0.72481(7) 0.8089(5) 0.63084(18) 0.0244(7) Uani 1 d . .
C31 C 0.69689(7) 0.9652(5) 0.64282(18) 0.0285(7) Uani 1 d . .
H31 H 0.7012 1.0998 0.6768 0.034 Uiso 1 calc . .
C32 C 0.66365(7) 0.9247(5) 0.60585(18) 0.0294(7) Uani 1 d . .
H32 H 0.6454 1.0326 0.6145 0.035 Uiso 1 calc . .
C33 C 0.60712(8) 0.9019(6) 0.4571(2) 0.0436(9) Uani 1 d . .
H33A H 0.6242 0.9353 0.4142 0.065 Uiso 1 calc . .
H33B H 0.6052 1.0358 0.495 0.065 Uiso 1 calc . .
H33C H 0.5841 0.8691 0.4279 0.065 Uiso 1 calc . .
C34 C 0.83184(8) 0.9478(6) 0.7102(2) 0.0376(8) Uani 1 d . .
H34A H 0.8574 0.9508 0.7224 0.056 Uiso 1 calc . .
H34B H 0.8201 0.9581 0.7644 0.056 Uiso 1 calc . .
H34C H 0.8247 1.079 0.6733 0.056 Uiso 1 calc . .
N2 N 0.56215(7) 0.3645(5) 0.75145(18) 0.0418(7) Uani 1 d . .
C35 C 0.53786(9) 0.5223(6) 0.7659(2) 0.0501(9) Uani 1 d . .
H35A H 0.5358 0.6524 0.7287 0.06 Uiso 0.714(18) calc A 1
H35B H 0.5358 0.6524 0.7287 0.06 Uiso 0.286(18) calc A 2
C36 C 0.51529(9) 0.5077(7) 0.8321(2) 0.0530(10) Uani 1 d . .
H36A H 0.4997 0.6311 0.8433 0.064 Uiso 0.714(18) calc A 1
H36B H 0.4948 0.6023 0.8288 0.064 Uiso 0.286(18) calc A 2
C37A C 0.5160(2) 0.3045(14) 0.8828(5) 0.0403(17) Uani 0.714(18) d A 1
C38A C 0.53985(19) 0.1372(16) 0.8645(6) 0.051(2) Uani 0.714(18) d A 1
H38A H 0.5413 -0.0006 0.8977 0.061 Uiso 0.714(18) calc A 1
C39A C 0.5619(3) 0.1666(16) 0.7982(6) 0.051(2) Uani 0.714(18) d A 1
H39A H 0.5773 0.0445 0.7849 0.061 Uiso 0.714(18) calc A 1
C37B C 0.5202(6) 0.376(4) 0.8972(13) 0.052(4) Uani 0.286(18) d A 2
C38B C 0.5477(5) 0.229(4) 0.8900(13) 0.054(4) Uani 0.286(18) d A 2
H38B H 0.5526 0.1205 0.9349 0.065 Uiso 0.286(18) calc A 2
C39B C 0.5688(6) 0.229(4) 0.8213(13) 0.046(4) Uani 0.286(18) d A 2
H39B H 0.5888 0.1294 0.8231 0.055 Uiso 0.286(18) calc A 2
C40A C 0.49105(18) 0.2736(18) 0.9548(4) 0.0493(19) Uani 0.714(18) d . .
H40A H 0.4675 0.3368 0.9366 0.059 Uiso 0.714(18) calc A 1
H40B H 0.4883 0.1071 0.9674 0.059 Uiso 0.714(18) calc A 1
C40B C 0.4947(6) 0.395(6) 0.9672(12) 0.073(6) Uani 0.286(18) d . .
H40C H 0.4907 0.5595 0.9806 0.088 Uiso 0.286(18) calc A 2
H40D H 0.4718 0.3258 0.9471 0.088 Uiso 0.286(18) calc A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.324(4) . ?
O1 H1 0.84 . ?
O2 C1 1.214(4) . ?
O3 C8 1.375(3) . ?
O3 C14 1.427(4) . ?
O4 C21 1.320(4) . ?
O4 H4A 0.84 . ?
O5 C21 1.218(4) . ?
O6 C28 1.375(3) . ?
O6 C34 1.428(4) . ?
N1 C15 1.337(4) . ?
N1 C19 1.340(4) . ?
C1 C2 1.516(4) . ?
C2 C3 1.519(4) . ?
C2 C13 1.531(4) . ?
C2 H2 1 . ?
C3 C12 1.377(4) . ?
C3 C4 1.419(4) . ?
C4 C5 1.372(4) . ?
C4 H4 0.95 . ?
C5 C6 1.421(4) . ?
C5 H5 0.95 . ?
C6 C11 1.420(4) . ?
C6 C7 1.429(4) . ?
C7 C8 1.368(4) . ?
C7 H7 0.95 . ?
C8 C9 1.416(4) . ?
C9 C10 1.365(4) . ?
C9 H9 0.95 . ?
C10 C11 1.425(4) . ?
C10 H10 0.95 . ?
C11 C12 1.415(4) . ?
C12 H12 0.95 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 C16 1.385(4) . ?
C15 H15 0.95 . ?
C16 C17 1.388(4) . ?
C16 H16 0.95 . ?
C17 C18 1.383(4) . ?
C17 C20 1.511(4) . ?
C18 C19 1.384(4) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 C20 1.536(6) 2_656 ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 C22 1.512(4) . ?
C22 C23 1.524(4) . ?
C22 C33 1.537(4) . ?
C22 H22 1 . ?
C23 C24 1.375(4) . ?
C23 C32 1.418(4) . ?
C24 C25 1.424(4) . ?
C24 H24 0.95 . ?
C25 C26 1.416(4) . ?
C25 C30 1.420(4) . ?
C26 C27 1.366(4) . ?
C26 H26 0.95 . ?
C27 C28 1.417(4) . ?
C27 H27 0.95 . ?
C28 C29 1.370(4) . ?
C29 C30 1.429(4) . ?
C29 H29 0.95 . ?
C30 C31 1.416(4) . ?
C31 C32 1.375(4) . ?
C31 H31 0.95 . ?
C32 H32 0.95 . ?
C33 H33A 0.98 . ?
C33 H33B 0.98 . ?
C33 H33C 0.98 . ?
C34 H34A 0.98 . ?
C34 H34B 0.98 . ?
C34 H34C 0.98 . ?
N2 C35 1.328(4) . ?
N2 C39B 1.353(18) . ?
N2 C39A 1.358(8) . ?
C35 C36 1.386(4) . ?
C35 H35A 0.95 . ?
C35 H35B 0.95 . ?
C36 C37B 1.271(19) . ?
C36 C37A 1.416(8) . ?
C36 H36A 0.95 . ?
C36 H36B 0.95 . ?
C37A C38A 1.371(8) . ?
C37A C40A 1.523(8) . ?
C38A C39A 1.379(8) . ?
C38A H38A 0.95 . ?
C39A H39A 0.95 . ?
C37B C38B 1.36(2) . ?
C37B C40B 1.51(2) . ?
C38B C39B 1.378(19) . ?
C38B H38B 0.95 . ?
C39B H39B 0.95 . ?
C40A C40B 1.475(15) 2_657 ?
C40A H40A 0.99 . ?
C40A H40B 0.99 . ?
C40B C40A 1.475(15) 2_657 ?
C40B H40C 0.99 . ?
C40B H40D 0.99 . ?

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 H1 109.5 . . ?
C8 O3 C14 117.5(2) . . ?
C21 O4 H4A 109.5 . . ?
C28 O6 C34 116.8(2) . . ?
C15 N1 C19 116.8(3) . . ?
O2 C1 O1 123.2(3) . . ?
O2 C1 C2 124.5(3) . . ?
O1 C1 C2 112.2(3) . . ?
C1 C2 C3 109.3(2) . . ?
C1 C2 C13 111.1(3) . . ?
C3 C2 C13 112.4(3) . . ?
C1 C2 H2 108 . . ?
C3 C2 H2 108 . . ?
C13 C2 H2 108 . . ?
C12 C3 C4 117.9(3) . . ?
C12 C3 C2 120.9(3) . . ?
C4 C3 C2 121.2(3) . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C11 C6 C5 117.6(3) . . ?
C11 C6 C7 119.9(3) . . ?
C5 C6 C7 122.4(3) . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 O3 125.6(3) . . ?
C7 C8 C9 120.8(3) . . ?
O3 C8 C9 113.6(3) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C6 119.7(3) . . ?
C12 C11 C10 122.0(3) . . ?
C6 C11 C10 118.2(3) . . ?
C3 C12 C11 122.1(3) . . ?
C3 C12 H12 119 . . ?
C11 C12 H12 119 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 123.0(3) . . ?
N1 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120 . . ?
C17 C16 H16 120 . . ?
C18 C17 C16 116.9(3) . . ?
C18 C17 C20 121.2(3) . . ?
C16 C17 C20 121.9(3) . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
N1 C19 C18 123.5(3) . . ?
N1 C19 H19 118.3 . . ?
C18 C19 H19 118.3 . . ?
C17 C20 C20 112.3(3) . 2_656 ?
C17 C20 H20A 109.1 . . ?
C20 C20 H20A 109.1 2_656 . ?
C17 C20 H20B 109.1 . . ?
C20 C20 H20B 109.1 2_656 . ?
H20A C20 H20B 107.9 . . ?
O5 C21 O4 122.4(3) . . ?
O5 C21 C22 124.7(3) . . ?
O4 C21 C22 112.9(3) . . ?
C21 C22 C23 109.6(2) . . ?
C21 C22 C33 111.7(3) . . ?
C23 C22 C33 112.5(2) . . ?
C21 C22 H22 107.6 . . ?
C23 C22 H22 107.6 . . ?
C33 C22 H22 107.6 . . ?
C24 C23 C32 118.4(3) . . ?
C24 C23 C22 121.3(3) . . ?
C32 C23 C22 120.3(3) . . ?
C23 C24 C25 121.7(3) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C26 C25 C30 118.6(2) . . ?
C26 C25 C24 122.3(3) . . ?
C30 C25 C24 119.1(3) . . ?
C27 C26 C25 121.1(3) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 120.3(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 C28 O6 125.9(3) . . ?
C29 C28 C27 120.5(3) . . ?
O6 C28 C27 113.6(2) . . ?
C28 C29 C30 119.9(3) . . ?
C28 C29 H29 120 . . ?
C30 C29 H29 120 . . ?
C31 C30 C25 118.5(3) . . ?
C31 C30 C29 121.9(3) . . ?
C25 C30 C29 119.5(3) . . ?
C32 C31 C30 120.8(3) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C23 121.3(3) . . ?
C31 C32 H32 119.3 . . ?
C23 C32 H32 119.3 . . ?
C22 C33 H33A 109.5 . . ?
C22 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C22 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C35 N2 C39B 111.1(10) . . ?
C35 N2 C39A 117.4(5) . . ?
N2 C35 C36 123.7(3) . . ?
N2 C35 H35A 118.2 . . ?
C36 C35 H35A 118.2 . . ?
N2 C35 H35B 118.2 . . ?
C36 C35 H35B 118.2 . . ?
C37B C36 C35 124.2(10) . . ?
C35 C36 C37A 118.4(5) . . ?
C35 C36 H36A 120.8 . . ?
C37A C36 H36A 120.8 . . ?
C37B C36 H36B 117.9 . . ?
C35 C36 H36B 117.9 . . ?
C38A C37A C36 117.3(6) . . ?
C38A C37A C40A 121.5(6) . . ?
C36 C37A C40A 121.2(6) . . ?
C37A C38A C39A 120.7(7) . . ?
C37A C38A H38A 119.7 . . ?
C39A C38A H38A 119.7 . . ?
N2 C39A C38A 122.1(7) . . ?
N2 C39A H39A 119 . . ?
C38A C39A H39A 119 . . ?
C36 C37B C38B 112.6(16) . . ?
C36 C37B C40B 117.6(16) . . ?
C38B C37B C40B 129.6(17) . . ?
C37B C38B C39B 123.7(18) . . ?
C37B C38B H38B 118.1 . . ?
C39B C38B H38B 118.1 . . ?
N2 C39B C38B 122.2(18) . . ?
N2 C39B H39B 118.9 . . ?
C38B C39B H39B 118.9 . . ?
C40B C40A C37A 109.7(7) 2_657 . ?
C40B C40A H40A 109.7 2_657 . ?
C37A C40A H40A 109.7 . . ?
C40B C40A H40B 109.7 2_657 . ?
C37A C40A H40B 109.7 . . ?
H40A C40A H40B 108.2 . . ?
C40A C40B C37B 110.0(14) 2_657 . ?
C40A C40B H40C 109.7 2_657 . ?
C37B C40B H40C 109.7 . . ?
C40A C40B H40D 109.7 2_657 . ?
C37B C40B H40D 109.7 . . ?
H40C C40B H40D 108.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 1.82 2.659(3) 176 .
O4 H4A N2 0.84 1.84 2.680(3) 173.8 .

_chemical_name_systematic        
'co-crystal of naproxen and 1,2-Bis(4-pyridyl)ethane'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_mefenamicacidAzo
_database_code_depnum_ccdc_archive 'CCDC 1864915'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_mefenamicacidAzo    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
RESPONSE: These reflections were not collected using only omega scans.
;
# end Validation Reply Form

_audit_creation_date             2018-02-22T13:49:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H19 N3 O2'
_chemical_formula_weight         333.38

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.549(5)
_cell_length_b                   8.736(6)
_cell_length_c                   13.095(8)
_cell_angle_alpha                100.617(10)
_cell_angle_beta                 99.729(9)
_cell_angle_gamma                93.918(9)
_cell_volume                     832.2(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2243
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      26.72

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_F_000             352

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7034
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.995

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_number            9970
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.292
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_number_total             3726
_reflns_number_gt                2666
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.0716P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3726
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.86840(14) -0.19859(12) 0.08852(8) 0.0233(3) Uani 1 d . .
H1 H 0.8298 -0.294 0.0733 0.035 Uiso 1 calc . .
O2 O 0.73683(15) -0.20794(12) 0.22755(8) 0.0259(3) Uani 1 d . .
N1 N 0.75863(17) 0.05133(14) 0.37421(9) 0.0218(3) Uani 1 d . .
H1A H 0.7309 -0.0508 0.3573 0.026 Uiso 1 calc . .
N2 N 0.75021(16) 0.49538(14) 0.03929(9) 0.0198(3) Uani 1 d . .
N3 N 0.53142(16) 0.02467(14) -0.03567(9) 0.0210(3) Uani 1 d . .
C1 C 0.84911(19) 0.12134(17) 0.30996(11) 0.0174(3) Uani 1 d . .
C2 C 0.88791(18) 0.03488(16) 0.21496(11) 0.0169(3) Uani 1 d . .
C3 C 0.98748(19) 0.11041(17) 0.15425(11) 0.0190(3) Uani 1 d . .
H3 H 1.0151 0.0518 0.0913 0.023 Uiso 1 calc . .
C4 C 1.0464(2) 0.26795(18) 0.18362(12) 0.0223(3) Uani 1 d . .
H4 H 1.1148 0.3174 0.1419 0.027 Uiso 1 calc . .
C5 C 1.0041(2) 0.35286(17) 0.27528(12) 0.0222(3) Uani 1 d . .
H5 H 1.0422 0.4618 0.2955 0.027 Uiso 1 calc . .
C6 C 0.9082(2) 0.28241(17) 0.33724(11) 0.0204(3) Uani 1 d . .
H6 H 0.8812 0.3434 0.3996 0.025 Uiso 1 calc . .
C7 C 0.82356(19) -0.13312(17) 0.17911(11) 0.0185(3) Uani 1 d . .
C8 C 0.7067(2) 0.13524(16) 0.46732(11) 0.0197(3) Uani 1 d . .
C9 C 0.5435(2) 0.20208(17) 0.46060(11) 0.0194(3) Uani 1 d . .
C10 C 0.4950(2) 0.28026(17) 0.55421(11) 0.0198(3) Uani 1 d . .
C11 C 0.6108(2) 0.28986(17) 0.64995(12) 0.0226(3) Uani 1 d . .
H11 H 0.5778 0.342 0.7132 0.027 Uiso 1 calc . .
C12 C 0.7736(2) 0.22484(18) 0.65513(12) 0.0245(4) Uani 1 d . .
H12 H 0.852 0.234 0.7213 0.029 Uiso 1 calc . .
C13 C 0.8215(2) 0.14679(18) 0.56389(12) 0.0228(3) Uani 1 d . .
H13 H 0.9324 0.1011 0.5671 0.027 Uiso 1 calc . .
C14 C 0.4216(2) 0.1942(2) 0.35584(12) 0.0270(4) Uani 1 d . .
H14A H 0.4148 0.3 0.3414 0.041 Uiso 1 calc . .
H14B H 0.3005 0.1484 0.358 0.041 Uiso 1 calc . .
H14C H 0.4702 0.1292 0.2999 0.041 Uiso 1 calc . .
C15 C 0.3202(2) 0.3542(2) 0.55066(13) 0.0288(4) Uani 1 d . .
H15A H 0.3075 0.4015 0.6226 0.043 Uiso 1 calc . .
H15B H 0.2188 0.274 0.5191 0.043 Uiso 1 calc . .
H15C H 0.3204 0.4352 0.5079 0.043 Uiso 1 calc . .
C16 C 0.7757(2) 0.39476(17) -0.04624(12) 0.0224(3) Uani 1 d . .
H16 H 0.8473 0.4316 -0.0915 0.027 Uiso 1 calc . .
C17 C 0.7031(2) 0.24062(17) -0.07165(12) 0.0216(3) Uani 1 d . .
H17 H 0.7228 0.1731 -0.1335 0.026 Uiso 1 calc . .
C18 C 0.60126(19) 0.18678(16) -0.00520(11) 0.0184(3) Uani 1 d . .
C19 C 0.5724(2) 0.28855(17) 0.08400(12) 0.0213(3) Uani 1 d . .
H19 H 0.5017 0.2542 0.1306 0.026 Uiso 1 calc . .
C20 C 0.6497(2) 0.44073(17) 0.10254(12) 0.0213(3) Uani 1 d . .
H20 H 0.6309 0.5109 0.1635 0.026 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C7 1.3271(18) . ?
O1 H1 0.84 . ?
O2 C7 1.2219(17) . ?
N1 C1 1.3694(18) . ?
N1 C8 1.4315(18) . ?
N1 H1A 0.88 . ?
N2 C16 1.3406(19) . ?
N2 C20 1.3409(19) . ?
N3 N3 1.247(2) 2_655 ?
N3 C18 1.436(2) . ?
C1 C6 1.408(2) . ?
C1 C2 1.418(2) . ?
C2 C3 1.400(2) . ?
C2 C7 1.477(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.95 . ?
C4 C5 1.388(2) . ?
C4 H4 0.95 . ?
C5 C6 1.372(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C8 C13 1.390(2) . ?
C8 C9 1.395(2) . ?
C9 C10 1.408(2) . ?
C9 C14 1.504(2) . ?
C10 C11 1.387(2) . ?
C10 C15 1.506(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.95 . ?
C12 C13 1.379(2) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 C17 1.377(2) . ?
C16 H16 0.95 . ?
C17 C18 1.377(2) . ?
C17 H17 0.95 . ?
C18 C19 1.390(2) . ?
C19 C20 1.376(2) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?

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
C7 O1 H1 109.5 . . ?
C1 N1 C8 123.55(13) . . ?
C1 N1 H1A 118.2 . . ?
C8 N1 H1A 118.2 . . ?
C16 N2 C20 117.43(13) . . ?
N3 N3 C18 112.66(15) 2_655 . ?
N1 C1 C6 120.57(13) . . ?
N1 C1 C2 121.55(13) . . ?
C6 C1 C2 117.87(13) . . ?
C3 C2 C1 119.40(14) . . ?
C3 C2 C7 119.76(13) . . ?
C1 C2 C7 120.84(13) . . ?
C4 C3 C2 121.59(14) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.75(14) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.24(14) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 121.11(14) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O2 C7 O1 121.79(13) . . ?
O2 C7 C2 123.92(13) . . ?
O1 C7 C2 114.28(12) . . ?
C13 C8 C9 121.19(13) . . ?
C13 C8 N1 118.45(14) . . ?
C9 C8 N1 120.36(13) . . ?
C8 C9 C10 118.72(13) . . ?
C8 C9 C14 121.36(13) . . ?
C10 C9 C14 119.92(14) . . ?
C11 C10 C9 119.28(14) . . ?
C11 C10 C15 120.21(13) . . ?
C9 C10 C15 120.51(14) . . ?
C12 C11 C10 121.31(14) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 119.78(15) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 119.72(14) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 123.21(14) . . ?
N2 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
C16 C17 C18 118.36(14) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C19 119.68(14) . . ?
C17 C18 N3 115.48(13) . . ?
C19 C18 N3 124.84(13) . . ?
C20 C19 C18 117.75(14) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
N2 C20 C19 123.57(14) . . ?
N2 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.84 1.84 2.684(2) 178.6 1_545
N1 H1A O2 0.88 1.99 2.662(2) 132.4 .

_chemical_name_systematic        
"co-crystal of mefenamic acid and 4,4'-azopyridine"
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_naproxenBPP
_database_code_depnum_ccdc_archive 'CCDC 1864927'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_STRVA01_naproxenBPP         
;
PROBLEM: Flack test results are meaningless.
RESPONSE: The absolute configuration of the crystal was not determined in this
          study.
;
_vrf_PLAT911_hut18_19            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
RESPONSE: These reflections were not collected using omega only scans.
;
# end Validation Reply Form

_audit_creation_date             2018-02-21T08:44:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C41 H42 N2 O6'
_chemical_formula_weight         658.76
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   35.567(8)
_cell_length_b                   5.7333(15)
_cell_length_c                   33.199(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.732(4)
_cell_angle_gamma                90
_cell_volume                     6767(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7999
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.07

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.105
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             2800

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6928
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.991

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_number            40017
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         1.146
_diffrn_reflns_theta_max         27.127
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_number_total             14930
_reflns_number_gt                11453
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.0918P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         14930
_refine_ls_number_parameters     896
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 4176 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16794(5) 0.5032(4) 0.41674(6) 0.0316(5) Uani 1 d . .
O2 O 0.43440(6) 0.3254(4) 0.44296(7) 0.0413(6) Uani 1 d . .
O3 O 0.39451(6) 0.0334(4) 0.43274(7) 0.0367(6) Uani 1 d . .
H3A H 0.4093 -0.0002 0.4143 0.055 Uiso 1 calc . .
O4 O 0.33100(5) 0.4229(4) 0.33026(6) 0.0293(5) Uani 1 d . .
O5 O 0.10407(6) 0.8452(4) 0.31365(7) 0.0405(6) Uani 1 d . .
H5A H 0.0908 0.8924 0.3325 0.061 Uiso 1 calc . .
O6 O 0.06259(6) 0.5615(4) 0.31193(7) 0.0401(6) Uani 1 d . .
O7 O 0.17029(5) -0.0257(4) 0.16485(6) 0.0247(5) Uani 1 d . .
O8 O 0.40795(6) 0.4308(4) 0.22771(6) 0.0384(6) Uani 1 d . .
O9 O 0.40832(6) 0.2651(4) 0.16712(6) 0.0340(5) Uani 1 d . .
H9 H 0.4175 0.3942 0.1606 0.051 Uiso 1 calc . .
O10 O 0.32996(5) 0.0520(4) 0.07646(6) 0.0250(5) Uani 1 d . .
O11 O 0.09774(5) -0.4046(3) 0.06325(6) 0.0265(5) Uani 1 d . .
H11 H 0.0847 -0.4333 0.0833 0.04 Uiso 1 calc . .
O12 O 0.06774(5) -0.0633(4) 0.06527(6) 0.0316(5) Uani 1 d . .
N1 N 0.43059(6) 0.8755(4) 0.37187(7) 0.0233(6) Uani 1 d . .
N2 N 0.56478(6) 0.9833(4) 0.13015(7) 0.0230(5) Uani 1 d . .
N3 N 0.56961(6) 0.5388(4) 0.37328(7) 0.0228(5) Uani 1 d . .
N4 N 0.43238(6) 0.6366(4) 0.12581(7) 0.0208(5) Uani 1 d . .
C1 C 0.20426(8) 0.4486(5) 0.42767(8) 0.0239(7) Uani 1 d . .
C2 C 0.20802(8) 0.2361(5) 0.44935(8) 0.0265(7) Uani 1 d . .
H2 H 0.1863 0.1467 0.4549 0.032 Uiso 1 calc . .
C3 C 0.24246(8) 0.1592(5) 0.46228(8) 0.0243(7) Uani 1 d . .
H3 H 0.2446 0.0142 0.476 0.029 Uiso 1 calc . .
C4 C 0.27525(8) 0.2923(5) 0.45560(8) 0.0205(6) Uani 1 d . .
C5 C 0.31113(8) 0.2259(5) 0.47159(8) 0.0216(6) Uani 1 d . .
H5 H 0.3136 0.0829 0.4859 0.026 Uiso 1 calc . .
C6 C 0.34216(8) 0.3625(5) 0.46692(8) 0.0211(6) Uani 1 d . .
C7 C 0.33830(8) 0.5737(5) 0.44501(8) 0.0227(6) Uani 1 d . .
H7 H 0.3597 0.6698 0.4416 0.027 Uiso 1 calc . .
C8 C 0.30429(8) 0.6414(5) 0.42876(8) 0.0225(6) Uani 1 d . .
H8 H 0.3026 0.782 0.4137 0.027 Uiso 1 calc . .
C9 C 0.27135(8) 0.5050(5) 0.43403(8) 0.0202(6) Uani 1 d . .
C10 C 0.23534(7) 0.5786(5) 0.41957(8) 0.0226(6) Uani 1 d . .
H10 H 0.2328 0.7181 0.4043 0.027 Uiso 1 calc . .
C11 C 0.16257(9) 0.7054(6) 0.39216(10) 0.0348(8) Uani 1 d . .
H11A H 0.1357 0.7265 0.3859 0.052 Uiso 1 calc . .
H11B H 0.176 0.6859 0.367 0.052 Uiso 1 calc . .
H11C H 0.1723 0.8427 0.4066 0.052 Uiso 1 calc . .
C12 C 0.38021(8) 0.2915(5) 0.48503(8) 0.0248(7) Uani 1 d . .
H12 H 0.3762 0.1501 0.502 0.03 Uiso 1 calc . .
C13 C 0.40639(8) 0.2214(5) 0.45140(8) 0.0227(6) Uani 1 d . .
C14 C 0.39786(8) 0.4775(6) 0.51210(9) 0.0350(8) Uani 1 d . .
H14A H 0.3811 0.5109 0.5343 0.053 Uiso 1 calc . .
H14B H 0.4017 0.62 0.4964 0.053 Uiso 1 calc . .
H14C H 0.4221 0.4217 0.523 0.053 Uiso 1 calc . .
C15 C 0.29428(8) 0.4650(5) 0.31891(8) 0.0243(7) Uani 1 d . .
C16 C 0.28799(8) 0.6730(5) 0.29647(8) 0.0251(7) Uani 1 d . .
H16 H 0.3086 0.7704 0.2903 0.03 Uiso 1 calc . .
C17 C 0.25260(8) 0.7332(5) 0.28384(8) 0.0241(7) Uani 1 d . .
H17 H 0.2488 0.8751 0.2695 0.029 Uiso 1 calc . .
C18 C 0.22141(8) 0.5894(5) 0.29155(8) 0.0208(6) Uani 1 d . .
C19 C 0.18433(8) 0.6429(5) 0.27663(8) 0.0217(6) Uani 1 d . .
H19 H 0.18 0.7829 0.2619 0.026 Uiso 1 calc . .
C20 C 0.15484(8) 0.4941(5) 0.28331(8) 0.0224(7) Uani 1 d . .
C21 C 0.16183(8) 0.2872(5) 0.30570(8) 0.0255(7) Uani 1 d . .
H21 H 0.1416 0.1834 0.3103 0.031 Uiso 1 calc . .
C22 C 0.19682(8) 0.2335(5) 0.32073(9) 0.0253(7) Uani 1 d . .
H22 H 0.2005 0.0948 0.336 0.03 Uiso 1 calc . .
C23 C 0.22772(8) 0.3806(5) 0.31392(8) 0.0202(6) Uani 1 d . .
C24 C 0.26488(8) 0.3222(5) 0.32772(8) 0.0235(7) Uani 1 d . .
H24 H 0.2692 0.1843 0.343 0.028 Uiso 1 calc . .
C25 C 0.33840(8) 0.2215(6) 0.35468(9) 0.0303(7) Uani 1 d . .
H25A H 0.3654 0.2126 0.3614 0.045 Uiso 1 calc . .
H25B H 0.3306 0.0811 0.3398 0.045 Uiso 1 calc . .
H25C H 0.3243 0.2329 0.3795 0.045 Uiso 1 calc . .
C26 C 0.11479(7) 0.5387(5) 0.26788(8) 0.0230(6) Uani 1 d . .
H26 H 0.1034 0.3836 0.2611 0.028 Uiso 1 calc . .
C27 C 0.09106(8) 0.6483(5) 0.30027(8) 0.0213(6) Uani 1 d . .
C28 C 0.11220(8) 0.6872(6) 0.22977(9) 0.0360(8) Uani 1 d . .
H28A H 0.1216 0.8444 0.2357 0.054 Uiso 1 calc . .
H28B H 0.0859 0.6966 0.2202 0.054 Uiso 1 calc . .
H28C H 0.1274 0.616 0.2089 0.054 Uiso 1 calc . .
C29 C 0.20770(7) 0.0013(5) 0.17536(8) 0.0200(6) Uani 1 d . .
C30 C 0.23538(7) -0.1490(5) 0.16533(8) 0.0200(6) Uani 1 d . .
H30 H 0.2295 -0.2839 0.1498 0.024 Uiso 1 calc . .
C31 C 0.27345(8) -0.1040(5) 0.17816(8) 0.0180(6) Uani 1 d . .
C32 C 0.30298(7) -0.2571(5) 0.16918(8) 0.0216(6) Uani 1 d . .
H32 H 0.2977 -0.3934 0.1537 0.026 Uiso 1 calc . .
C33 C 0.33894(8) -0.2130(5) 0.18227(8) 0.0221(6) Uani 1 d . .
H33 H 0.3583 -0.32 0.176 0.026 Uiso 1 calc . .
C34 C 0.34812(7) -0.0099(5) 0.20512(8) 0.0179(6) Uani 1 d . .
C35 C 0.31975(7) 0.1421(5) 0.21384(8) 0.0193(6) Uani 1 d . .
H35 H 0.3255 0.2787 0.229 0.023 Uiso 1 calc . .
C36 C 0.28192(7) 0.1001(5) 0.20072(8) 0.0182(6) Uani 1 d . .
C37 C 0.25218(8) 0.2529(5) 0.21027(8) 0.0213(6) Uani 1 d . .
H37 H 0.2575 0.3912 0.2252 0.026 Uiso 1 calc . .
C38 C 0.21600(8) 0.2034(5) 0.19827(8) 0.0221(6) Uani 1 d . .
H38 H 0.1963 0.3056 0.2054 0.026 Uiso 1 calc . .
C39 C 0.16063(8) -0.2196(5) 0.13967(8) 0.0267(7) Uani 1 d . .
H39A H 0.1676 -0.3648 0.1535 0.04 Uiso 1 calc . .
H39B H 0.1742 -0.2084 0.1145 0.04 Uiso 1 calc . .
H39C H 0.1335 -0.2188 0.1337 0.04 Uiso 1 calc . .
C40 C 0.38838(7) 0.0279(5) 0.22035(8) 0.0196(6) Uani 1 d . .
H40 H 0.4043 -0.097 0.2086 0.023 Uiso 1 calc . .
C41 C 0.40294(7) 0.2623(5) 0.20606(8) 0.0205(6) Uani 1 d . .
C42 C 0.39146(8) 0.0072(6) 0.26618(8) 0.0271(7) Uani 1 d . .
H42A H 0.4178 0.024 0.2751 0.041 Uiso 1 calc . .
H42B H 0.3821 -0.1458 0.2744 0.041 Uiso 1 calc . .
H42C H 0.3764 0.13 0.2784 0.041 Uiso 1 calc . .
C43 C 0.29312(7) 0.0001(5) 0.06739(8) 0.0196(6) Uani 1 d . .
C44 C 0.26294(7) 0.1372(5) 0.07633(8) 0.0187(6) Uani 1 d . .
H44 H 0.2667 0.2779 0.091 0.022 Uiso 1 calc . .
C45 C 0.22617(7) 0.0690(5) 0.06361(7) 0.0170(6) Uani 1 d . .
C46 C 0.19424(7) 0.2117(5) 0.06977(8) 0.0189(6) Uani 1 d . .
H46 H 0.1971 0.3526 0.0846 0.023 Uiso 1 calc . .
C47 C 0.15957(7) 0.1498(5) 0.05469(8) 0.0202(6) Uani 1 d . .
H47 H 0.1387 0.2492 0.059 0.024 Uiso 1 calc . .
C48 C 0.15402(7) -0.0591(5) 0.03276(8) 0.0173(6) Uani 1 d . .
C49 C 0.18426(7) -0.2028(5) 0.02726(7) 0.0173(6) Uani 1 d . .
H49 H 0.1807 -0.3454 0.0131 0.021 Uiso 1 calc . .
C50 C 0.22067(7) -0.1434(5) 0.04226(8) 0.0173(6) Uani 1 d . .
C51 C 0.25259(7) -0.2843(5) 0.03485(8) 0.0195(6) Uani 1 d . .
H51 H 0.2494 -0.4305 0.0217 0.023 Uiso 1 calc . .
C52 C 0.28778(8) -0.2120(5) 0.04636(8) 0.0213(6) Uani 1 d . .
H52 H 0.3089 -0.3052 0.0402 0.026 Uiso 1 calc . .
C53 C 0.33672(8) 0.2569(5) 0.10015(9) 0.0265(7) Uani 1 d . .
H53A H 0.3247 0.2401 0.1262 0.04 Uiso 1 calc . .
H53B H 0.3262 0.393 0.0859 0.04 Uiso 1 calc . .
H53C H 0.3639 0.2781 0.1046 0.04 Uiso 1 calc . .
C54 C 0.11530(7) -0.1230(5) 0.01547(8) 0.0201(6) Uani 1 d . .
H54 H 0.1181 -0.2631 -0.0021 0.024 Uiso 1 calc . .
C55 C 0.09051(7) -0.1909(5) 0.05024(8) 0.0192(6) Uani 1 d . .
C56 C 0.09779(8) 0.0706(5) -0.01011(8) 0.0280(7) Uani 1 d . .
H56A H 0.0943 0.2095 0.0066 0.042 Uiso 1 calc . .
H56B H 0.0733 0.0189 -0.0212 0.042 Uiso 1 calc . .
H56C H 0.1144 0.1083 -0.0322 0.042 Uiso 1 calc . .
C57 C 0.41597(8) 0.6782(5) 0.35689(9) 0.0262(7) Uani 1 d . .
H57 H 0.3924 0.6278 0.3663 0.031 Uiso 1 calc . .
C58 C 0.43331(7) 0.5440(5) 0.32852(8) 0.0232(6) Uani 1 d . .
H58 H 0.4215 0.4066 0.3184 0.028 Uiso 1 calc . .
C59 C 0.46826(7) 0.6102(5) 0.31471(8) 0.0188(6) Uani 1 d . .
C60 C 0.48326(7) 0.8173(5) 0.32957(8) 0.0220(6) Uani 1 d . .
H60 H 0.5067 0.8725 0.3205 0.026 Uiso 1 calc . .
C61 C 0.46375(8) 0.9425(5) 0.35774(8) 0.0232(7) Uani 1 d . .
H61 H 0.4745 1.084 0.3676 0.028 Uiso 1 calc . .
C62 C 0.48854(8) 0.4528(5) 0.28601(8) 0.0241(7) Uani 1 d . .
H62A H 0.4694 0.3694 0.2692 0.029 Uiso 1 calc . .
H62B H 0.5025 0.3341 0.3022 0.029 Uiso 1 calc . .
C63 C 0.51618(8) 0.5682(5) 0.25781(8) 0.0245(7) Uani 1 d . .
H63A H 0.5353 0.6541 0.2742 0.029 Uiso 1 calc . .
H63B H 0.5293 0.4452 0.2427 0.029 Uiso 1 calc . .
C64 C 0.49745(8) 0.7363(5) 0.22784(8) 0.0258(7) Uani 1 d . .
H64A H 0.4753 0.6577 0.2153 0.031 Uiso 1 calc . .
H64B H 0.4882 0.8726 0.2429 0.031 Uiso 1 calc . .
C65 C 0.52201(7) 0.8239(5) 0.19467(8) 0.0215(6) Uani 1 d . .
C66 C 0.51374(8) 1.0310(6) 0.17481(8) 0.0269(7) Uani 1 d . .
H66 H 0.4931 1.1237 0.1828 0.032 Uiso 1 calc . .
C67 C 0.53542(7) 1.1021(5) 0.14348(8) 0.0256(7) Uani 1 d . .
H67 H 0.5291 1.2451 0.1305 0.031 Uiso 1 calc . .
C68 C 0.57338(9) 0.7874(5) 0.14961(9) 0.0307(7) Uani 1 d . .
H68 H 0.5943 0.6996 0.141 0.037 Uiso 1 calc . .
C69 C 0.55334(8) 0.7039(5) 0.18189(9) 0.0305(7) Uani 1 d . .
H69 H 0.5611 0.5645 0.1952 0.037 Uiso 1 calc . .
C70 C 0.53738(8) 0.4638(5) 0.38852(8) 0.0231(7) Uani 1 d . .
H70 H 0.5269 0.322 0.3785 0.028 Uiso 1 calc . .
C71 C 0.51859(7) 0.5818(5) 0.41801(8) 0.0230(6) Uani 1 d . .
H71 H 0.4957 0.5214 0.4278 0.028 Uiso 1 calc . .
C72 C 0.53326(8) 0.7892(5) 0.43325(8) 0.0220(6) Uani 1 d . .
C73 C 0.56686(8) 0.8663(5) 0.41752(8) 0.0235(7) Uani 1 d . .
H73 H 0.5781 1.0067 0.4272 0.028 Uiso 1 calc . .
C74 C 0.58390(8) 0.7386(5) 0.38783(8) 0.0253(7) Uani 1 d . .
H74 H 0.6067 0.7951 0.3773 0.03 Uiso 1 calc . .
C75 C 0.51456(8) 0.9259(6) 0.46577(8) 0.0282(7) Uani 1 d . .
H75A H 0.4932 1.0143 0.4535 0.034 Uiso 1 calc . .
H75B H 0.5328 1.0403 0.4772 0.034 Uiso 1 calc . .
C76 C 0.5 0.7755(8) 0.5 0.0271(10) Uani 1 d . .
H76A H 0.5205 0.674 0.5106 0.033 Uiso 0.5 calc . .
H76B H 0.4795 0.674 0.4894 0.033 Uiso 0.5 calc . .
C77 C 0.41657(8) 0.8301(5) 0.11063(8) 0.0218(6) Uani 1 d . .
H77 H 0.3927 0.8763 0.12 0.026 Uiso 1 calc . .
C78 C 0.43326(7) 0.9660(5) 0.08192(8) 0.0207(6) Uani 1 d . .
H78 H 0.4208 1.102 0.0721 0.025 Uiso 1 calc . .
C79 C 0.46805(7) 0.9067(5) 0.06713(8) 0.0190(6) Uani 1 d . .
C80 C 0.48473(7) 0.7071(5) 0.08332(8) 0.0234(7) Uani 1 d . .
H80 H 0.5087 0.6586 0.0748 0.028 Uiso 1 calc . .
C81 C 0.46627(8) 0.5798(5) 0.11184(8) 0.0262(7) Uani 1 d . .
H81 H 0.4782 0.4435 0.1223 0.031 Uiso 1 calc . .
C82 C 0.48601(8) 1.0471(5) 0.03464(8) 0.0245(7) Uani 1 d . .
H82A H 0.5075 1.1354 0.0467 0.029 Uiso 1 calc . .
H82B H 0.4675 1.1617 0.0238 0.029 Uiso 1 calc . .
C83 C 0.5 0.9001(8) 0 0.0271(10) Uani 1 d . .
H83A H 0.5207 0.7984 0.0101 0.032 Uiso 0.5 calc . .
H83B H 0.4793 0.7984 -0.0101 0.032 Uiso 0.5 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.367(3) . ?
O1 C11 1.427(4) . ?
O2 C13 1.201(3) . ?
O3 C13 1.307(3) . ?
O3 H3A 0.84 . ?
O4 C15 1.370(3) . ?
O4 C25 1.430(4) . ?
O5 C27 1.294(3) . ?
O5 H5A 0.84 . ?
O6 C27 1.203(3) . ?
O7 C29 1.374(3) . ?
O7 C39 1.427(3) . ?
O8 C41 1.214(3) . ?
O9 C41 1.313(3) . ?
O9 H9 0.84 . ?
O10 C43 1.368(3) . ?
O10 C53 1.430(3) . ?
O11 C55 1.322(3) . ?
O11 H11 0.84 . ?
O12 C55 1.210(3) . ?
N1 C57 1.335(4) . ?
N1 C61 1.339(3) . ?
N2 C68 1.327(4) . ?
N2 C67 1.334(3) . ?
N3 C74 1.338(4) . ?
N3 C70 1.338(3) . ?
N4 C77 1.336(3) . ?
N4 C81 1.345(3) . ?
C1 C10 1.367(4) . ?
C1 C2 1.420(4) . ?
C2 C3 1.359(4) . ?
C2 H2 0.95 . ?
C3 C4 1.417(4) . ?
C3 H3 0.95 . ?
C4 C9 1.419(4) . ?
C4 C5 1.419(4) . ?
C5 C6 1.366(4) . ?
C5 H5 0.95 . ?
C6 C7 1.417(4) . ?
C6 C12 1.520(4) . ?
C7 C8 1.365(4) . ?
C7 H7 0.95 . ?
C8 C9 1.424(4) . ?
C8 H8 0.95 . ?
C9 C10 1.418(4) . ?
C10 H10 0.95 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 C14 1.518(4) . ?
C12 C13 1.529(4) . ?
C12 H12 1 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 C24 1.367(4) . ?
C15 C16 1.420(4) . ?
C16 C17 1.359(4) . ?
C16 H16 0.95 . ?
C17 C18 1.412(4) . ?
C17 H17 0.95 . ?
C18 C23 1.423(4) . ?
C18 C19 1.428(4) . ?
C19 C20 1.375(4) . ?
C19 H19 0.95 . ?
C20 C21 1.418(4) . ?
C20 C26 1.521(4) . ?
C21 C22 1.362(4) . ?
C21 H21 0.95 . ?
C22 C23 1.409(4) . ?
C22 H22 0.95 . ?
C23 C24 1.425(4) . ?
C24 H24 0.95 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
C26 C27 1.522(4) . ?
C26 C28 1.525(4) . ?
C26 H26 1 . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
C29 C30 1.357(4) . ?
C29 C38 1.412(4) . ?
C30 C31 1.430(4) . ?
C30 H30 0.95 . ?
C31 C32 1.408(4) . ?
C31 C36 1.417(4) . ?
C32 C33 1.362(4) . ?
C32 H32 0.95 . ?
C33 C34 1.422(4) . ?
C33 H33 0.95 . ?
C34 C35 1.371(4) . ?
C34 C40 1.519(4) . ?
C35 C36 1.422(4) . ?
C35 H35 0.95 . ?
C36 C37 1.417(4) . ?
C37 C38 1.365(4) . ?
C37 H37 0.95 . ?
C38 H38 0.95 . ?
C39 H39A 0.98 . ?
C39 H39B 0.98 . ?
C39 H39C 0.98 . ?
C40 C41 1.521(4) . ?
C40 C42 1.527(4) . ?
C40 H40 1 . ?
C42 H42A 0.98 . ?
C42 H42B 0.98 . ?
C42 H42C 0.98 . ?
C43 C44 1.370(4) . ?
C43 C52 1.413(4) . ?
C44 C45 1.417(4) . ?
C44 H44 0.95 . ?
C45 C50 1.419(4) . ?
C45 C46 1.420(4) . ?
C46 C47 1.364(4) . ?
C46 H46 0.95 . ?
C47 C48 1.412(4) . ?
C47 H47 0.95 . ?
C48 C49 1.372(4) . ?
C48 C54 1.521(4) . ?
C49 C50 1.415(4) . ?
C49 H49 0.95 . ?
C50 C51 1.421(4) . ?
C51 C52 1.362(4) . ?
C51 H51 0.95 . ?
C52 H52 0.95 . ?
C53 H53A 0.98 . ?
C53 H53B 0.98 . ?
C53 H53C 0.98 . ?
C54 C56 1.520(4) . ?
C54 C55 1.524(4) . ?
C54 H54 1 . ?
C56 H56A 0.98 . ?
C56 H56B 0.98 . ?
C56 H56C 0.98 . ?
C57 C58 1.377(4) . ?
C57 H57 0.95 . ?
C58 C59 1.391(4) . ?
C58 H58 0.95 . ?
C59 C60 1.386(4) . ?
C59 C62 1.511(4) . ?
C60 C61 1.382(4) . ?
C60 H60 0.95 . ?
C61 H61 0.95 . ?
C62 C63 1.528(4) . ?
C62 H62A 0.99 . ?
C62 H62B 0.99 . ?
C63 C64 1.524(4) . ?
C63 H63A 0.99 . ?
C63 H63B 0.99 . ?
C64 C65 1.512(4) . ?
C64 H64A 0.99 . ?
C64 H64B 0.99 . ?
C65 C66 1.385(4) . ?
C65 C69 1.387(4) . ?
C66 C67 1.375(4) . ?
C66 H66 0.95 . ?
C67 H67 0.95 . ?
C68 C69 1.390(4) . ?
C68 H68 0.95 . ?
C69 H69 0.95 . ?
C70 C71 1.379(4) . ?
C70 H70 0.95 . ?
C71 C72 1.388(4) . ?
C71 H71 0.95 . ?
C72 C73 1.391(4) . ?
C72 C75 1.505(4) . ?
C73 C74 1.382(4) . ?
C73 H73 0.95 . ?
C74 H74 0.95 . ?
C75 C76 1.529(4) . ?
C75 H75A 0.99 . ?
C75 H75B 0.99 . ?
C76 C75 1.529(4) 2_656 ?
C76 H76A 0.99 . ?
C76 H76B 0.99 . ?
C77 C78 1.379(4) . ?
C77 H77 0.95 . ?
C78 C79 1.387(3) . ?
C78 H78 0.95 . ?
C79 C80 1.390(4) . ?
C79 C82 1.504(4) . ?
C80 C81 1.378(4) . ?
C80 H80 0.95 . ?
C81 H81 0.95 . ?
C82 C83 1.522(4) . ?
C82 H82A 0.99 . ?
C82 H82B 0.99 . ?
C83 C82 1.522(4) 2_655 ?
C83 H83A 0.99 . ?
C83 H83B 0.99 . ?

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 C11 116.5(2) . . ?
C13 O3 H3A 109.5 . . ?
C15 O4 C25 117.1(2) . . ?
C27 O5 H5A 109.5 . . ?
C29 O7 C39 116.8(2) . . ?
C41 O9 H9 109.5 . . ?
C43 O10 C53 116.3(2) . . ?
C55 O11 H11 109.5 . . ?
C57 N1 C61 116.8(3) . . ?
C68 N2 C67 116.2(3) . . ?
C74 N3 C70 117.3(3) . . ?
C77 N4 C81 116.3(2) . . ?
C10 C1 O1 125.9(3) . . ?
C10 C1 C2 120.2(3) . . ?
O1 C1 C2 113.9(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C9 118.3(3) . . ?
C3 C4 C5 122.1(3) . . ?
C9 C4 C5 119.5(3) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 118.8(3) . . ?
C5 C6 C12 121.0(3) . . ?
C7 C6 C12 120.2(3) . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C4 120.0(3) . . ?
C10 C9 C8 122.2(3) . . ?
C4 C9 C8 117.7(3) . . ?
C1 C10 C9 119.9(3) . . ?
C1 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C6 113.2(2) . . ?
C14 C12 C13 111.5(2) . . ?
C6 C12 C13 109.6(2) . . ?
C14 C12 H12 107.4 . . ?
C6 C12 H12 107.4 . . ?
C13 C12 H12 107.4 . . ?
O2 C13 O3 123.8(3) . . ?
O2 C13 C12 124.6(3) . . ?
O3 C13 C12 111.6(2) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C24 C15 O4 124.4(3) . . ?
C24 C15 C16 120.4(3) . . ?
O4 C15 C16 115.2(3) . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 121.4(3) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C23 118.3(3) . . ?
C17 C18 C19 122.3(3) . . ?
C23 C18 C19 119.4(3) . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 118.8(3) . . ?
C19 C20 C26 123.5(3) . . ?
C21 C20 C26 117.7(3) . . ?
C22 C21 C20 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 118.4(3) . . ?
C22 C23 C24 121.9(3) . . ?
C18 C23 C24 119.7(3) . . ?
C15 C24 C23 119.9(3) . . ?
C15 C24 H24 120 . . ?
C23 C24 H24 120 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C26 C27 111.4(2) . . ?
C20 C26 C28 113.9(2) . . ?
C27 C26 C28 109.6(2) . . ?
C20 C26 H26 107.2 . . ?
C27 C26 H26 107.2 . . ?
C28 C26 H26 107.2 . . ?
O6 C27 O5 123.1(3) . . ?
O6 C27 C26 123.1(3) . . ?
O5 C27 C26 113.7(2) . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 O7 124.8(3) . . ?
C30 C29 C38 120.8(3) . . ?
O7 C29 C38 114.5(2) . . ?
C29 C30 C31 120.0(3) . . ?
C29 C30 H30 120 . . ?
C31 C30 H30 120 . . ?
C32 C31 C36 118.6(2) . . ?
C32 C31 C30 122.0(3) . . ?
C36 C31 C30 119.4(2) . . ?
C33 C32 C31 121.1(3) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C32 C33 C34 121.4(3) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 H33 119.3 . . ?
C35 C34 C33 118.3(2) . . ?
C35 C34 C40 122.1(2) . . ?
C33 C34 C40 119.6(2) . . ?
C34 C35 C36 121.6(3) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C37 C36 C31 118.7(2) . . ?
C37 C36 C35 122.2(3) . . ?
C31 C36 C35 119.1(2) . . ?
C38 C37 C36 120.7(3) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C37 C38 C29 120.5(3) . . ?
C37 C38 H38 119.8 . . ?
C29 C38 H38 119.8 . . ?
O7 C39 H39A 109.5 . . ?
O7 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O7 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C34 C40 C41 110.4(2) . . ?
C34 C40 C42 111.0(2) . . ?
C41 C40 C42 111.4(2) . . ?
C34 C40 H40 108 . . ?
C41 C40 H40 108 . . ?
C42 C40 H40 108 . . ?
O8 C41 O9 123.4(3) . . ?
O8 C41 C40 124.3(3) . . ?
O9 C41 C40 112.3(2) . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O10 C43 C44 125.4(3) . . ?
O10 C43 C52 114.2(2) . . ?
C44 C43 C52 120.4(3) . . ?
C43 C44 C45 119.9(3) . . ?
C43 C44 H44 120 . . ?
C45 C44 H44 120 . . ?
C44 C45 C50 119.9(2) . . ?
C44 C45 C46 122.2(3) . . ?
C50 C45 C46 117.9(2) . . ?
C47 C46 C45 121.0(3) . . ?
C47 C46 H46 119.5 . . ?
C45 C46 H46 119.5 . . ?
C46 C47 C48 121.4(3) . . ?
C46 C47 H47 119.3 . . ?
C48 C47 H47 119.3 . . ?
C49 C48 C47 118.7(3) . . ?
C49 C48 C54 120.7(2) . . ?
C47 C48 C54 120.7(2) . . ?
C48 C49 C50 121.4(3) . . ?
C48 C49 H49 119.3 . . ?
C50 C49 H49 119.3 . . ?
C49 C50 C45 119.6(2) . . ?
C49 C50 C51 122.0(3) . . ?
C45 C50 C51 118.4(2) . . ?
C52 C51 C50 120.7(3) . . ?
C52 C51 H51 119.6 . . ?
C50 C51 H51 119.6 . . ?
C51 C52 C43 120.6(3) . . ?
C51 C52 H52 119.7 . . ?
C43 C52 H52 119.7 . . ?
O10 C53 H53A 109.5 . . ?
O10 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
O10 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C56 C54 C48 112.7(2) . . ?
C56 C54 C55 111.9(2) . . ?
C48 C54 C55 108.3(2) . . ?
C56 C54 H54 107.9 . . ?
C48 C54 H54 107.9 . . ?
C55 C54 H54 107.9 . . ?
O12 C55 O11 123.5(3) . . ?
O12 C55 C54 124.6(3) . . ?
O11 C55 C54 111.9(2) . . ?
C54 C56 H56A 109.5 . . ?
C54 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C54 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
N1 C57 C58 123.4(3) . . ?
N1 C57 H57 118.3 . . ?
C58 C57 H57 118.3 . . ?
C57 C58 C59 119.8(3) . . ?
C57 C58 H58 120.1 . . ?
C59 C58 H58 120.1 . . ?
C60 C59 C58 117.1(3) . . ?
C60 C59 C62 123.3(2) . . ?
C58 C59 C62 119.5(3) . . ?
C61 C60 C59 119.3(3) . . ?
C61 C60 H60 120.3 . . ?
C59 C60 H60 120.3 . . ?
N1 C61 C60 123.6(3) . . ?
N1 C61 H61 118.2 . . ?
C60 C61 H61 118.2 . . ?
C59 C62 C63 117.1(2) . . ?
C59 C62 H62A 108 . . ?
C63 C62 H62A 108 . . ?
C59 C62 H62B 108 . . ?
C63 C62 H62B 108 . . ?
H62A C62 H62B 107.3 . . ?
C64 C63 C62 113.4(2) . . ?
C64 C63 H63A 108.9 . . ?
C62 C63 H63A 108.9 . . ?
C64 C63 H63B 108.9 . . ?
C62 C63 H63B 108.9 . . ?
H63A C63 H63B 107.7 . . ?
C65 C64 C63 115.8(2) . . ?
C65 C64 H64A 108.3 . . ?
C63 C64 H64A 108.3 . . ?
C65 C64 H64B 108.3 . . ?
C63 C64 H64B 108.3 . . ?
H64A C64 H64B 107.4 . . ?
C66 C65 C69 116.1(3) . . ?
C66 C65 C64 120.8(3) . . ?
C69 C65 C64 123.0(3) . . ?
C67 C66 C65 119.9(3) . . ?
C67 C66 H66 120.1 . . ?
C65 C66 H66 120.1 . . ?
N2 C67 C66 124.2(3) . . ?
N2 C67 H67 117.9 . . ?
C66 C67 H67 117.9 . . ?
N2 C68 C69 123.4(3) . . ?
N2 C68 H68 118.3 . . ?
C69 C68 H68 118.3 . . ?
C65 C69 C68 120.0(3) . . ?
C65 C69 H69 120 . . ?
C68 C69 H69 120 . . ?
N3 C70 C71 123.4(3) . . ?
N3 C70 H70 118.3 . . ?
C71 C70 H70 118.3 . . ?
C70 C71 C72 119.6(3) . . ?
C70 C71 H71 120.2 . . ?
C72 C71 H71 120.2 . . ?
C71 C72 C73 117.0(3) . . ?
C71 C72 C75 122.5(3) . . ?
C73 C72 C75 120.5(3) . . ?
C74 C73 C72 120.0(3) . . ?
C74 C73 H73 120 . . ?
C72 C73 H73 120 . . ?
N3 C74 C73 122.8(3) . . ?
N3 C74 H74 118.6 . . ?
C73 C74 H74 118.6 . . ?
C72 C75 C76 114.0(3) . . ?
C72 C75 H75A 108.8 . . ?
C76 C75 H75A 108.8 . . ?
C72 C75 H75B 108.8 . . ?
C76 C75 H75B 108.8 . . ?
H75A C75 H75B 107.6 . . ?
C75 C76 C75 111.4(4) . 2_656 ?
C75 C76 H76A 109.4 . . ?
C75 C76 H76A 109.4 2_656 . ?
C75 C76 H76B 109.4 . . ?
C75 C76 H76B 109.4 2_656 . ?
H76A C76 H76B 108 . . ?
N4 C77 C78 123.0(3) . . ?
N4 C77 H77 118.5 . . ?
C78 C77 H77 118.5 . . ?
C77 C78 C79 120.9(3) . . ?
C77 C78 H78 119.6 . . ?
C79 C78 H78 119.6 . . ?
C78 C79 C80 116.1(3) . . ?
C78 C79 C82 121.7(3) . . ?
C80 C79 C82 122.2(2) . . ?
C81 C80 C79 119.7(3) . . ?
C81 C80 H80 120.2 . . ?
C79 C80 H80 120.2 . . ?
N4 C81 C80 124.0(3) . . ?
N4 C81 H81 118 . . ?
C80 C81 H81 118 . . ?
C79 C82 C83 113.7(3) . . ?
C79 C82 H82A 108.8 . . ?
C83 C82 H82A 108.8 . . ?
C79 C82 H82B 108.8 . . ?
C83 C82 H82B 108.8 . . ?
H82A C82 H82B 107.7 . . ?
C82 C83 C82 112.7(3) 2_655 . ?
C82 C83 H83A 109 2_655 . ?
C82 C83 H83A 109 . . ?
C82 C83 H83B 109 2_655 . ?
C82 C83 H83B 109 . . ?
H83A C83 H83B 107.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9 N4 0.84 1.89 2.687(3) 157.2 .
O3 H3A N1 0.84 1.77 2.590(3) 164.4 1_545
O5 H5A N3 0.84 1.78 2.608(3) 168.2 3_455
O11 H11 N2 0.84 1.79 2.623(3) 169.2 3_435


# END of CIF
_chemical_name_systematic        
'co-crystal of naproxen and 1,3-Bis(4-pyridyl)propane'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_mefenamicacidBPEth
_database_code_depnum_ccdc_archive 'CCDC 1864914'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;

_audit_creation_date             2018-02-15T08:36:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C21 H21 N2 O2'
_chemical_formula_weight         333.4

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.450(7)
_cell_length_b                   7.835(7)
_cell_length_c                   16.895(16)
_cell_angle_alpha                94.30(3)
_cell_angle_beta                 93.160(17)
_cell_angle_gamma                117.89(2)
_cell_volume                     864.5(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4014
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.41

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       chip
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.335
_exptl_crystal_size_min          0.125
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             354

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6871
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.99

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_number            15696
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.431
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_number_total             3912
_reflns_number_gt                2909
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.1860P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.02872(16) 0.52410(15) 0.14111(6) 0.0461(3) Uani 1 d . .
H1 H -0.0351 0.407 0.1216 0.069 Uiso 1 calc . .
O2 O 0.22989(18) 0.42160(15) 0.19800(7) 0.0555(3) Uani 1 d . .
N1 N 0.52304(17) 0.65668(16) 0.30901(7) 0.0367(3) Uani 1 d . .
H1A H 0.4456 0.5374 0.286 0.044 Uiso 1 calc . .
N2 N 0.83501(19) 1.15888(18) 0.08185(7) 0.0427(3) Uani 1 d . .
C1 C 0.4728(2) 0.79532(18) 0.28732(8) 0.0306(3) Uani 1 d . .
C2 C 0.3077(2) 0.74896(18) 0.22950(7) 0.0301(3) Uani 1 d . .
C3 C 0.2584(2) 0.8935(2) 0.21092(8) 0.0382(3) Uani 1 d . .
H3 H 0.1458 0.8612 0.1727 0.046 Uiso 1 calc . .
C4 C 0.3677(3) 1.0800(2) 0.24628(9) 0.0479(4) Uani 1 d . .
H4 H 0.3324 1.1769 0.233 0.057 Uiso 1 calc . .
C5 C 0.5312(3) 1.1252(2) 0.30186(9) 0.0470(4) Uani 1 d . .
H5 H 0.6092 1.2552 0.3264 0.056 Uiso 1 calc . .
C6 C 0.5831(2) 0.9872(2) 0.32230(9) 0.0387(3) Uani 1 d . .
H6 H 0.6959 1.0227 0.3609 0.046 Uiso 1 calc . .
C7 C 0.1870(2) 0.55141(19) 0.18923(8) 0.0342(3) Uani 1 d . .
C8 C 0.68756(19) 0.68584(18) 0.36495(8) 0.0321(3) Uani 1 d . .
C9 C 0.68807(19) 0.72814(18) 0.44644(8) 0.0314(3) Uani 1 d . .
C10 C 0.84741(19) 0.74016(18) 0.49912(8) 0.0331(3) Uani 1 d . .
C11 C 0.9993(2) 0.7092(2) 0.46909(9) 0.0383(3) Uani 1 d . .
H11 H 1.1069 0.717 0.5046 0.046 Uiso 1 calc . .
C12 C 0.9973(2) 0.6674(2) 0.38861(9) 0.0419(4) Uani 1 d . .
H12 H 1.1028 0.6458 0.3688 0.05 Uiso 1 calc . .
C13 C 0.8423(2) 0.6566(2) 0.33633(9) 0.0376(3) Uani 1 d . .
H13 H 0.842 0.629 0.2806 0.045 Uiso 1 calc . .
C14 C 0.5196(2) 0.7544(2) 0.47926(9) 0.0403(3) Uani 1 d . .
H14A H 0.5745 0.8872 0.5057 0.06 Uiso 1 calc . .
H14B H 0.4578 0.6616 0.518 0.06 Uiso 1 calc . .
H14C H 0.4158 0.7318 0.4357 0.06 Uiso 1 calc . .
C15 C 0.8492(2) 0.7776(2) 0.58729(9) 0.0427(4) Uani 1 d . .
H15A H 0.9614 0.7652 0.6146 0.064 Uiso 1 calc . .
H15B H 0.7192 0.6829 0.6042 0.064 Uiso 1 calc . .
H15C H 0.8683 0.9093 0.6009 0.064 Uiso 1 calc . .
C16 C 0.8116(3) 1.0327(2) 0.13372(9) 0.0523(4) Uani 1 d . .
H16 H 0.8478 1.0799 0.1888 0.063 Uiso 1 calc . .
C17 C 0.7383(3) 0.8384(2) 0.11204(10) 0.0517(4) Uani 1 d . .
H17 H 0.7209 0.7532 0.1515 0.062 Uiso 1 calc . .
C18 C 0.6900(2) 0.7673(2) 0.03281(9) 0.0431(4) Uani 1 d . .
C19 C 0.7122(3) 0.8983(2) -0.02078(10) 0.0549(4) Uani 1 d . .
H19 H 0.6776 0.8551 -0.0762 0.066 Uiso 1 calc . .
C20 C 0.7837(3) 1.0903(2) 0.00560(9) 0.0513(4) Uani 1 d . .
H20 H 0.7972 1.1779 -0.0324 0.062 Uiso 1 calc . .
C21 C 0.6141(2) 0.5555(2) 0.00604(11) 0.0520(4) Uani 1 d . .
H21A H 0.6698 0.5426 -0.0446 0.062 Uiso 1 calc . .
H21B H 0.6647 0.4989 0.0465 0.062 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C7 1.3149(19) . ?
O1 H1 0.84 . ?
O2 C7 1.2166(18) . ?
N1 C1 1.3708(19) . ?
N1 C8 1.4232(19) . ?
N1 H1A 0.88 . ?
N2 C20 1.321(2) . ?
N2 C16 1.327(2) . ?
C1 C6 1.394(2) . ?
C1 C2 1.413(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.463(2) . ?
C3 C4 1.363(2) . ?
C3 H3 0.95 . ?
C4 C5 1.382(2) . ?
C4 H4 0.95 . ?
C5 C6 1.368(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C8 C13 1.381(2) . ?
C8 C9 1.391(2) . ?
C9 C10 1.406(2) . ?
C9 C14 1.492(2) . ?
C10 C11 1.378(2) . ?
C10 C15 1.495(2) . ?
C11 C12 1.372(2) . ?
C11 H11 0.95 . ?
C12 C13 1.381(2) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 C17 1.366(3) . ?
C16 H16 0.95 . ?
C17 C18 1.371(2) . ?
C17 H17 0.95 . ?
C18 C19 1.377(2) . ?
C18 C21 1.503(3) . ?
C19 C20 1.367(3) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 C21 1.497(3) 2_665 ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?

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
C7 O1 H1 109.5 . . ?
C1 N1 C8 126.71(11) . . ?
C1 N1 H1A 116.6 . . ?
C8 N1 H1A 116.6 . . ?
C20 N2 C16 117.37(15) . . ?
N1 C1 C6 120.74(14) . . ?
N1 C1 C2 121.44(12) . . ?
C6 C1 C2 117.82(12) . . ?
C3 C2 C1 119.48(12) . . ?
C3 C2 C7 119.56(14) . . ?
C1 C2 C7 120.96(12) . . ?
C4 C3 C2 121.64(15) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.64(14) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.49(14) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 120.92(15) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O2 C7 O1 121.86(13) . . ?
O2 C7 C2 123.19(14) . . ?
O1 C7 C2 114.94(12) . . ?
C13 C8 C9 120.24(12) . . ?
C13 C8 N1 117.54(14) . . ?
C9 C8 N1 122.06(13) . . ?
C8 C9 C10 119.22(13) . . ?
C8 C9 C14 121.39(12) . . ?
C10 C9 C14 119.36(14) . . ?
C11 C10 C9 119.41(14) . . ?
C11 C10 C15 119.68(13) . . ?
C9 C10 C15 120.86(13) . . ?
C12 C11 C10 120.94(13) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.10(14) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.09(15) . . ?
C12 C13 H13 120 . . ?
C8 C13 H13 120 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 123.41(15) . . ?
N2 C16 H16 118.3 . . ?
C17 C16 H16 118.3 . . ?
C16 C17 C18 119.42(16) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 116.99(16) . . ?
C17 C18 C21 121.28(15) . . ?
C19 C18 C21 121.73(16) . . ?
C20 C19 C18 120.16(16) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
N2 C20 C19 122.61(16) . . ?
N2 C20 H20 118.7 . . ?
C19 C20 H20 118.7 . . ?
C21 C21 C18 112.02(17) 2_665 . ?
C21 C21 H21A 109.2 2_665 . ?
C18 C21 H21A 109.2 . . ?
C21 C21 H21B 109.2 2_665 . ?
C18 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.84 1.77 2.612(3) 178.4 1_445
N1 H1A O2 0.88 1.95 2.636(2) 134.2 .

_chemical_name_systematic        
'co-crystal of mefenamic acid and 1,2-Bis(4-pyridyl)ethane'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_naproxenAzo
_database_code_depnum_ccdc_archive 'CCDC 1864926'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_naproxenAzo         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: These reflections were not collected using only omega scans.
;
# end Validation Reply Form

_audit_creation_date             2018-02-16T12:45:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C38 H36 N4 O6'
_chemical_formula_weight         644.71
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   15.483(7)
_cell_length_b                   5.745(2)
_cell_length_c                   19.668(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.025(8)
_cell_angle_gamma                90
_cell_volume                     1643.5(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5422
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      26.84

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       blade
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.095
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             680

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6912
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.992

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_number            19374
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.102
_diffrn_reflns_theta_max         27.14
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_number_total             7221
_reflns_number_gt                6035
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7221
_refine_ls_number_parameters     439
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.05
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 2299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.91184(10) 0.8971(3) 1.15472(8) 0.0223(4) Uani 1 d . .
O2 O 0.73563(12) 0.4857(3) 0.69067(10) 0.0296(4) Uani 1 d . .
H2A H 0.68 0.4632 0.6663 0.044 Uiso 1 calc . .
O3 O 0.70219(12) 0.8499(3) 0.65040(10) 0.0379(5) Uani 1 d . .
O4 O -0.40880(10) 0.3813(3) -0.15025(8) 0.0226(4) Uani 1 d . .
O5 O -0.22250(11) 0.0741(3) 0.31238(9) 0.0318(4) Uani 1 d . .
H5A H -0.1676 0.0612 0.3399 0.048 Uiso 1 calc . .
O6 O -0.21021(13) 0.4232(4) 0.36484(11) 0.0507(6) Uani 1 d . .
N1 N 0.55774(13) 0.4063(4) 0.61539(10) 0.0261(5) Uani 1 d . .
N2 N 0.27365(13) 0.3232(4) 0.50996(10) 0.0242(5) Uani 1 d . .
N3 N 0.24733(13) 0.1158(4) 0.49484(9) 0.0247(5) Uani 1 d . .
N4 N -0.03879(13) 0.0518(4) 0.39218(10) 0.0264(5) Uani 1 d . .
C1 C 0.89703(14) 0.8531(4) 1.08300(12) 0.0178(5) Uani 1 d . .
C2 C 0.93545(14) 0.6416(4) 1.07024(12) 0.0191(5) Uani 1 d . .
H2 H 0.9674 0.5442 1.1099 0.023 Uiso 1 calc . .
C3 C 0.92731(13) 0.5754(4) 1.00179(11) 0.0181(5) Uani 1 d . .
H3 H 0.9516 0.4298 0.9942 0.022 Uiso 1 calc . .
C4 C 0.88292(14) 0.7216(4) 0.94169(11) 0.0154(5) Uani 1 d . .
C5 C 0.88261(14) 0.6710(4) 0.87103(12) 0.0175(5) Uani 1 d . .
H5 H 0.9096 0.53 0.8629 0.021 Uiso 1 calc . .
C6 C 0.84459(14) 0.8196(4) 0.81443(12) 0.0188(5) Uani 1 d . .
C7 C 0.80092(15) 1.0258(4) 0.82639(12) 0.0197(5) Uani 1 d . .
H7 H 0.7723 1.1275 0.787 0.024 Uiso 1 calc . .
C8 C 0.79954(14) 1.0801(4) 0.89400(11) 0.0182(5) Uani 1 d . .
H8 H 0.7694 1.218 0.9005 0.022 Uiso 1 calc . .
C9 C 0.84244(14) 0.9337(4) 0.95429(12) 0.0162(5) Uani 1 d . .
C10 C 0.84898(14) 0.9958(4) 1.02619(11) 0.0167(5) Uani 1 d . .
H10 H 0.8206 1.1338 1.0348 0.02 Uiso 1 calc . .
C11 C 0.87534(16) 1.1081(5) 1.17194(12) 0.0255(5) Uani 1 d . .
H11A H 0.8997 1.2406 1.1528 0.038 Uiso 1 calc . .
H11B H 0.8931 1.1227 1.2246 0.038 Uiso 1 calc . .
H11C H 0.8082 1.1058 1.1503 0.038 Uiso 1 calc . .
C12 C 0.85057(15) 0.7685(4) 0.74004(12) 0.0221(5) Uani 1 d . .
H12 H 0.8907 0.6289 0.7443 0.026 Uiso 1 calc . .
C13 C 0.75536(16) 0.7100(4) 0.68853(13) 0.0230(5) Uani 1 d . .
C14 C 0.89253(17) 0.9714(4) 0.71162(13) 0.0283(6) Uani 1 d . .
H14A H 0.897 0.9295 0.6646 0.042 Uiso 1 calc . .
H14B H 0.954 1.0052 0.746 0.042 Uiso 1 calc . .
H14C H 0.8535 1.1093 0.7061 0.042 Uiso 1 calc . .
C15 C 0.52546(17) 0.2101(5) 0.57811(12) 0.0262(5) Uani 1 d . .
H15 H 0.5682 0.0923 0.5775 0.031 Uiso 1 calc . .
C16 C 0.43367(16) 0.1710(4) 0.54086(12) 0.0243(5) Uani 1 d . .
H16 H 0.4135 0.0315 0.5142 0.029 Uiso 1 calc . .
C17 C 0.37121(16) 0.3422(4) 0.54345(12) 0.0221(5) Uani 1 d . .
C18 C 0.40348(17) 0.5499(4) 0.57998(12) 0.0262(6) Uani 1 d . .
H18 H 0.3625 0.6722 0.5805 0.031 Uiso 1 calc . .
C19 C 0.49677(16) 0.5720(5) 0.61529(12) 0.0287(6) Uani 1 d . .
H19 H 0.5191 0.7121 0.6409 0.034 Uiso 1 calc . .
C20 C 0.14940(15) 0.0997(4) 0.46228(11) 0.0227(5) Uani 1 d . .
C21 C 0.11470(17) -0.0928(5) 0.41920(13) 0.0289(6) Uani 1 d . .
H21 H 0.1544 -0.2113 0.4133 0.035 Uiso 1 calc . .
C22 C 0.02003(16) -0.1073(5) 0.38473(13) 0.0299(6) Uani 1 d . .
H22 H -0.004 -0.2373 0.3543 0.036 Uiso 1 calc . .
C23 C -0.00371(17) 0.2340(4) 0.43580(12) 0.0270(6) Uani 1 d . .
H23 H -0.045 0.3475 0.442 0.032 Uiso 1 calc . .
C24 C 0.08892(16) 0.2644(4) 0.47193(13) 0.0260(6) Uani 1 d . .
H24 H 0.111 0.3948 0.5027 0.031 Uiso 1 calc . .
C25 C -0.39419(14) 0.3497(4) -0.07787(11) 0.0177(5) Uani 1 d . .
C26 C -0.43212(14) 0.1409(4) -0.06221(12) 0.0190(5) Uani 1 d . .
H26 H -0.4628 0.0366 -0.1003 0.023 Uiso 1 calc . .
C27 C -0.42506(13) 0.0880(4) 0.00709(11) 0.0178(5) Uani 1 d . .
H27 H -0.4495 -0.0549 0.0168 0.021 Uiso 1 calc . .
C28 C -0.38180(14) 0.2433(4) 0.06480(11) 0.0157(5) Uani 1 d . .
C29 C -0.38134(14) 0.2047(4) 0.13626(11) 0.0179(5) Uani 1 d . .
H29 H -0.4082 0.0666 0.1466 0.022 Uiso 1 calc . .
C30 C -0.34274(14) 0.3630(4) 0.19085(11) 0.0194(5) Uani 1 d . .
C31 C -0.29955(14) 0.5640(4) 0.17546(12) 0.0206(5) Uani 1 d . .
H31 H -0.2706 0.6713 0.2132 0.025 Uiso 1 calc . .
C32 C -0.29885(14) 0.6061(4) 0.10698(11) 0.0181(5) Uani 1 d . .
H32 H -0.2693 0.7419 0.0981 0.022 Uiso 1 calc . .
C33 C -0.34155(14) 0.4507(4) 0.04909(11) 0.0155(5) Uani 1 d . .
C34 C -0.34786(14) 0.5008(4) -0.02323(11) 0.0166(5) Uani 1 d . .
H34 H -0.3203 0.6375 -0.0338 0.02 Uiso 1 calc . .
C35 C -0.37378(16) 0.5904(5) -0.17026(12) 0.0258(5) Uani 1 d . .
H35A H -0.3882 0.5932 -0.2228 0.039 Uiso 1 calc . .
H35B H -0.307 0.5965 -0.1461 0.039 Uiso 1 calc . .
H35C H -0.4021 0.7252 -0.1556 0.039 Uiso 1 calc . .
C36 C -0.34889(16) 0.3293(4) 0.26603(12) 0.0239(5) Uani 1 d . .
H36 H -0.3875 0.1885 0.2645 0.029 Uiso 1 calc . .
C37 C -0.25360(17) 0.2840(5) 0.32016(13) 0.0270(6) Uani 1 d . .
C38 C -0.39466(17) 0.5370(5) 0.28842(13) 0.0311(6) Uani 1 d . .
H38A H -0.3583 0.6777 0.2897 0.047 Uiso 1 calc . .
H38B H -0.3982 0.5086 0.3365 0.047 Uiso 1 calc . .
H38C H -0.4568 0.5579 0.2534 0.047 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.373(3) . ?
O1 C11 1.426(3) . ?
O2 C13 1.328(3) . ?
O2 H2A 0.84 . ?
O3 C13 1.210(3) . ?
O4 C25 1.375(3) . ?
O4 C35 1.428(3) . ?
O5 C37 1.326(3) . ?
O5 H5A 0.84 . ?
O6 C37 1.208(3) . ?
N1 C19 1.340(3) . ?
N1 C15 1.344(3) . ?
N2 N3 1.261(3) . ?
N2 C17 1.431(3) . ?
N3 C20 1.433(3) . ?
N4 C22 1.333(3) . ?
N4 C23 1.344(3) . ?
C1 C10 1.380(3) . ?
C1 C2 1.413(3) . ?
C2 C3 1.363(3) . ?
C2 H2 0.95 . ?
C3 C4 1.421(3) . ?
C3 H3 0.95 . ?
C4 C5 1.418(3) . ?
C4 C9 1.430(3) . ?
C5 C6 1.366(3) . ?
C5 H5 0.95 . ?
C6 C7 1.423(3) . ?
C6 C12 1.526(3) . ?
C7 C8 1.373(3) . ?
C7 H7 0.95 . ?
C8 C9 1.420(3) . ?
C8 H8 0.95 . ?
C9 C10 1.428(3) . ?
C10 H10 0.95 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 C13 1.513(3) . ?
C12 C14 1.530(3) . ?
C12 H12 1 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 C16 1.376(3) . ?
C15 H15 0.95 . ?
C16 C17 1.392(3) . ?
C16 H16 0.95 . ?
C17 C18 1.394(3) . ?
C18 C19 1.378(3) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 C21 1.384(3) . ?
C20 C24 1.389(3) . ?
C21 C22 1.391(3) . ?
C21 H21 0.95 . ?
C22 H22 0.95 . ?
C23 C24 1.376(3) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
C25 C34 1.376(3) . ?
C25 C26 1.415(3) . ?
C26 C27 1.364(3) . ?
C26 H26 0.95 . ?
C27 C28 1.419(3) . ?
C27 H27 0.95 . ?
C28 C29 1.421(3) . ?
C28 C33 1.427(3) . ?
C29 C30 1.378(3) . ?
C29 H29 0.95 . ?
C30 C31 1.418(3) . ?
C30 C36 1.526(3) . ?
C31 C32 1.372(3) . ?
C31 H31 0.95 . ?
C32 C33 1.420(3) . ?
C32 H32 0.95 . ?
C33 C34 1.421(3) . ?
C34 H34 0.95 . ?
C35 H35A 0.98 . ?
C35 H35B 0.98 . ?
C35 H35C 0.98 . ?
C36 C37 1.517(3) . ?
C36 C38 1.527(3) . ?
C36 H36 1 . ?
C38 H38A 0.98 . ?
C38 H38B 0.98 . ?
C38 H38C 0.98 . ?

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 C11 117.39(17) . . ?
C13 O2 H2A 109.5 . . ?
C25 O4 C35 116.95(17) . . ?
C37 O5 H5A 109.5 . . ?
C19 N1 C15 117.7(2) . . ?
N3 N2 C17 112.7(2) . . ?
N2 N3 C20 111.9(2) . . ?
C22 N4 C23 117.5(2) . . ?
O1 C1 C10 125.2(2) . . ?
O1 C1 C2 114.12(19) . . ?
C10 C1 C2 120.7(2) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 122.2(2) . . ?
C5 C4 C9 119.34(19) . . ?
C3 C4 C9 118.38(19) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 118.8(2) . . ?
C5 C6 C12 120.7(2) . . ?
C7 C6 C12 120.5(2) . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.1(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 122.2(2) . . ?
C8 C9 C4 117.9(2) . . ?
C10 C9 C4 119.85(19) . . ?
C1 C10 C9 119.3(2) . . ?
C1 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C6 108.65(18) . . ?
C13 C12 C14 111.3(2) . . ?
C6 C12 C14 112.12(19) . . ?
C13 C12 H12 108.2 . . ?
C6 C12 H12 108.2 . . ?
C14 C12 H12 108.2 . . ?
O3 C13 O2 123.3(2) . . ?
O3 C13 C12 124.6(2) . . ?
O2 C13 C12 112.1(2) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 123.4(2) . . ?
N1 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C15 C16 C17 118.0(2) . . ?
C15 C16 H16 121 . . ?
C17 C16 H16 121 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 N2 124.5(2) . . ?
C18 C17 N2 116.0(2) . . ?
C19 C18 C17 117.9(2) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
N1 C19 C18 123.5(2) . . ?
N1 C19 H19 118.3 . . ?
C18 C19 H19 118.3 . . ?
C21 C20 C24 119.3(2) . . ?
C21 C20 N3 117.1(2) . . ?
C24 C20 N3 123.7(2) . . ?
C20 C21 C22 118.0(2) . . ?
C20 C21 H21 121 . . ?
C22 C21 H21 121 . . ?
N4 C22 C21 123.4(2) . . ?
N4 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?
N4 C23 C24 123.4(2) . . ?
N4 C23 H23 118.3 . . ?
C24 C23 H23 118.3 . . ?
C23 C24 C20 118.3(2) . . ?
C23 C24 H24 120.8 . . ?
C20 C24 H24 120.8 . . ?
O4 C25 C34 125.6(2) . . ?
O4 C25 C26 113.82(19) . . ?
C34 C25 C26 120.57(19) . . ?
C27 C26 C25 120.6(2) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 120.9(2) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C27 C28 C29 122.3(2) . . ?
C27 C28 C33 118.26(19) . . ?
C29 C28 C33 119.35(19) . . ?
C30 C29 C28 121.4(2) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 C31 118.8(2) . . ?
C29 C30 C36 121.1(2) . . ?
C31 C30 C36 120.0(2) . . ?
C32 C31 C30 121.1(2) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C33 121.2(2) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C32 C33 C34 121.9(2) . . ?
C32 C33 C28 118.01(19) . . ?
C34 C33 C28 120.02(19) . . ?
C25 C34 C33 119.5(2) . . ?
C25 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
O4 C35 H35A 109.5 . . ?
O4 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O4 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 C30 109.47(18) . . ?
C37 C36 C38 111.6(2) . . ?
C30 C36 C38 111.7(2) . . ?
C37 C36 H36 108 . . ?
C30 C36 H36 108 . . ?
C38 C36 H36 108 . . ?
O6 C37 O5 123.5(2) . . ?
O6 C37 C36 124.2(2) . . ?
O5 C37 C36 112.3(2) . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A N1 0.84 1.84 2.682(3) 178 .
O5 H5A N4 0.84 1.91 2.741(3) 172.3 .

_chemical_name_systematic        "co-crystal of naproxen and 4,4'-azopyridine"
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
