# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Ethenzamide-24Dihydroxybenzoicacid
_database_code_depnum_ccdc_archive 'CCDC 1504465'
_audit_update_record             
;
2016-12-18 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Ethenzamide-24Dihydroxybenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 O4, C9 H11 N O2'
_chemical_formula_sum            'C16 H16 N O6'
_chemical_formula_weight         318.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6638(17)
_cell_length_b                   6.6901(11)
_cell_length_c                   24.670(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.732(8)
_cell_angle_gamma                90
_cell_volume                     1572.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3751
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      24.66

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12804
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.675
_diffrn_reflns_theta_max         26.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3224
_reflns_number_gt                2157
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0995P)²+0.0398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3224
_refine_ls_number_parameters     243
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1627
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.89369(17) 0.5723(2) 0.93113(6) 0.0475(4) Uani 1 1 d . . . . .
C2 C 0.80840(17) 0.2108(2) 0.87926(6) 0.0494(4) Uani 1 1 d . . . . .
C3 C 0.93786(18) 0.7589(3) 0.95893(6) 0.0522(4) Uani 1 1 d . . . . .
C4 C 0.90814(18) 0.3291(3) 0.85963(7) 0.0539(4) Uani 1 1 d . . . . .
H1 H 0.946577 0.287502 0.829403 0.065 Uiso 1 1 calc R U . . .
C5 C 0.94952(18) 0.5078(3) 0.88518(7) 0.0516(4) Uani 1 1 d . . . . .
C6 C 0.75221(19) 0.2717(3) 0.92455(7) 0.0568(5) Uani 1 1 d . . . . .
H3 H 0.686268 0.191986 0.937669 0.068 Uiso 1 1 calc R U . . .
C7 C 0.79354(19) 0.4499(3) 0.95030(7) 0.0535(4) Uani 1 1 d . . . . .
C8 C 0.47950(16) 0.3524(2) 0.79384(6) 0.0452(4) Uani 1 1 d . . . . .
C9 C 0.41301(17) 0.4123(2) 0.83736(6) 0.0505(4) Uani 1 1 d . . . . .
C10 C 0.3076(2) 0.2936(3) 0.85297(8) 0.0663(5) Uani 1 1 d . . . . .
H5 H 0.262618 0.334523 0.881562 0.080 Uiso 1 1 calc R U . . .
C11 C 0.3377(2) 0.0522(3) 0.78430(9) 0.0685(5) Uani 1 1 d . . . . .
H6 H 0.313995 -0.069546 0.766981 0.082 Uiso 1 1 calc R U . . .
C12 C 0.58862(17) 0.4709(2) 0.77110(6) 0.0490(4) Uani 1 1 d . . . . .
C13 C 0.44065(19) 0.1703(3) 0.76844(7) 0.0555(5) Uani 1 1 d . . . . .
H7 H 0.485389 0.127249 0.739993 0.067 Uiso 1 1 calc R U . . .
C14 C 0.4055(3) 0.6412(3) 0.91260(8) 0.0821(7) Uani 1 1 d . . . . .
H8 H 0.425117 0.533578 0.939131 0.098 Uiso 1 1 calc R U . . .
H9 H 0.304826 0.663366 0.905246 0.098 Uiso 1 1 calc R U . . .
C15 C 0.2700(2) 0.1164(3) 0.82621(9) 0.0714(6) Uani 1 1 d . . . . .
H10 H 0.198596 0.039313 0.836400 0.086 Uiso 1 1 calc R U . . .
C16 C 0.4787(3) 0.8259(4) 0.93480(9) 0.0949(8) Uani 1 1 d . . . . .
H12 H 0.451861 0.934475 0.909794 0.142 Uiso 1 1 calc R U . . .
H11 H 0.578321 0.806023 0.939163 0.142 Uiso 1 1 calc R U . . .
H13 H 0.453254 0.856759 0.969832 0.142 Uiso 1 1 calc R U . . .
H14 H 0.703(2) 0.708(3) 0.7785(8) 0.069(5) Uiso 1 1 d . . . . .
H15 H 0.587(2) 0.693(3) 0.8252(10) 0.093(7) Uiso 1 1 d . . . . .
H16 H 0.806(2) 0.000(3) 0.8232(9) 0.081(6) Uiso 1 1 d . . . . .
H17 H 1.074(3) 0.988(5) 0.9650(12) 0.126(9) Uiso 1 1 d . . . . .
N1 N 0.62792(19) 0.6476(2) 0.79204(7) 0.0641(4) Uani 1 1 d . . . . .
O1 O 1.03606(14) 0.8611(2) 0.94132(5) 0.0659(4) Uani 1 1 d D . . . .
O2 O 0.88345(14) 0.81734(18) 0.99926(5) 0.0670(4) Uani 1 1 d . . . . .
O3 O 0.76287(14) 0.03570(18) 0.85576(5) 0.0641(4) Uani 1 1 d . . . . .
O4 O 0.45427(13) 0.58924(18) 0.86293(5) 0.0630(4) Uani 1 1 d . . . . .
O5 O 0.63984(15) 0.40202(18) 0.73179(5) 0.0697(4) Uani 1 1 d . . . . .
H4 H 0.782(3) 0.613(5) 1.0032(11) 0.068(9) Uiso 0.707(4) 1 d . . P A 1
H2 H 1.042(7) 0.720(7) 0.893(2) 0.08(2) Uiso 0.293(4) 1 d D . P A 2
O6A O 0.7407(2) 0.5005(3) 0.99371(7) 0.0681(7) Uani 0.707(4) 1 d . . P A 1
O6B O 1.0376(5) 0.6105(6) 0.86926(16) 0.0577(15) Uani 0.293(4) 1 d D . P A 2


_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
C1 C5 1.403(2) . ?
C1 C7 1.409(2) . ?
C1 C3 1.453(2) . ?
C2 O3 1.348(2) . ?
C2 C6 1.384(2) . ?
C2 C4 1.395(2) . ?
C3 O2 1.2635(19) . ?
C3 O1 1.303(2) . ?
C4 C5 1.379(2) . ?
C4 H1 0.9300 . ?
C5 O6B 1.210(4) . ?
C6 C7 1.378(2) . ?
C6 H3 0.9300 . ?
C7 O6A 1.307(2) . ?
C8 C13 1.392(2) . ?
C8 C9 1.400(2) . ?
C8 C12 1.502(2) . ?
C9 O4 1.369(2) . ?
C9 C10 1.396(3) . ?
C10 C15 1.375(3) . ?
C10 H5 0.9300 . ?
C11 C13 1.378(3) . ?
C11 C15 1.382(3) . ?
C11 H6 0.9300 . ?
C12 O5 1.2491(19) . ?
C12 N1 1.320(2) . ?
C13 H7 0.9300 . ?
C14 O4 1.428(2) . ?
C14 C16 1.482(3) . ?
C14 H8 0.9700 . ?
C14 H9 0.9700 . ?
C15 H10 0.9300 . ?
C16 H12 0.9600 . ?
C16 H11 0.9600 . ?
C16 H13 0.9600 . ?
N1 H14 0.94(2) . ?
N1 H15 1.01(2) . ?
O1 H17 1.06(3) . ?
O3 H16 1.00(2) . ?
O6A H4 0.87(3) . ?
O6B H2 0.93(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C7 118.16(15) . . ?
C5 C1 C3 121.54(16) . . ?
C7 C1 C3 120.29(15) . . ?
O3 C2 C6 117.32(15) . . ?
O3 C2 C4 122.55(15) . . ?
C6 C2 C4 120.13(15) . . ?
O2 C3 O1 121.59(15) . . ?
O2 C3 C1 120.63(16) . . ?
O1 C3 C1 117.77(15) . . ?
C5 C4 C2 119.78(15) . . ?
C5 C4 H1 120.1 . . ?
C2 C4 H1 120.1 . . ?
O6B C5 C4 120.6(2) . . ?
O6B C5 C1 118.4(2) . . ?
C4 C5 C1 120.97(16) . . ?
C7 C6 C2 120.28(16) . . ?
C7 C6 H3 119.9 . . ?
C2 C6 H3 119.9 . . ?
O6A C7 C6 118.64(17) . . ?
O6A C7 C1 120.67(17) . . ?
C6 C7 C1 120.67(15) . . ?
C13 C8 C9 118.15(15) . . ?
C13 C8 C12 116.52(15) . . ?
C9 C8 C12 125.32(14) . . ?
O4 C9 C10 122.28(15) . . ?
O4 C9 C8 117.72(14) . . ?
C10 C9 C8 120.00(16) . . ?
C15 C10 C9 120.22(18) . . ?
C15 C10 H5 119.9 . . ?
C9 C10 H5 119.9 . . ?
C13 C11 C15 119.30(18) . . ?
C13 C11 H6 120.3 . . ?
C15 C11 H6 120.3 . . ?
O5 C12 N1 120.57(16) . . ?
O5 C12 C8 119.40(15) . . ?
N1 C12 C8 120.02(14) . . ?
C11 C13 C8 121.79(17) . . ?
C11 C13 H7 119.1 . . ?
C8 C13 H7 119.1 . . ?
O4 C14 C16 108.28(18) . . ?
O4 C14 H8 110.0 . . ?
C16 C14 H8 110.0 . . ?
O4 C14 H9 110.0 . . ?
C16 C14 H9 110.0 . . ?
H8 C14 H9 108.4 . . ?
C10 C15 C11 120.50(18) . . ?
C10 C15 H10 119.8 . . ?
C11 C15 H10 119.8 . . ?
C14 C16 H12 109.5 . . ?
C14 C16 H11 109.5 . . ?
H12 C16 H11 109.5 . . ?
C14 C16 H13 109.5 . . ?
H12 C16 H13 109.5 . . ?
H11 C16 H13 109.5 . . ?
C12 N1 H14 115.6(12) . . ?
C12 N1 H15 117.1(13) . . ?
H14 N1 H15 126.3(19) . . ?
C3 O1 H17 116.0(14) . . ?
C2 O3 H16 113.7(13) . . ?
C9 O4 C14 119.55(14) . . ?
C7 O6A H4 102.8(19) . . ?
C5 O6B H2 102(4) . . ?

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
C14 H8 O6A 0.97 2.50 3.056(3) 116.1 3_667
C14 H9 O6B 0.97 2.61 3.541(5) 161.1 1_455
N1 H14 O5 0.94(2) 2.05(2) 2.954(2) 161.8(16) 2_656
N1 H15 O4 1.01(2) 1.84(2) 2.649(2) 134.2(19) .
O3 H16 O5 1.00(2) 1.67(2) 2.6523(18) 169.0(19) 2_646
O1 H17 O2 1.06(3) 1.59(3) 2.6452(18) 175(2) 3_777
O6A H4 O2 0.87(3) 1.69(3) 2.520(2) 158(3) .
O6B H2 O1 0.93(2) 1.53(3) 2.445(4) 165(7) .

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_Ethenzamide-35Dihydroxybenzoicacid-dihydrate
_database_code_depnum_ccdc_archive 'CCDC 1504466'
_audit_update_record             
;
2016-12-18 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT306_Ethenzamide-35Dihydroxybenzoicacid-dihydrate 
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O16 Check
RESPONSE: H atoms are not included due to disorder
;
# Added during the CSD deposition process: Sunday 18 December 2016 06:54 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Ethenzamide-35Dihydroxybenzoicacid dihydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N O2, 3(C7 H6 O4), 2(H2 O)'
_chemical_formula_sum            'C30 H33 N O16'
_chemical_formula_weight         663.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1756(12)
_cell_length_b                   11.7633(14)
_cell_length_c                   12.2009(14)
_cell_angle_alpha                95.319(8)
_cell_angle_beta                 102.434(7)
_cell_angle_gamma                100.852(7)
_cell_volume                     1523.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2162
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      20.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21929
_diffrn_reflns_av_unetI/netI     0.1180
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.726
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6190
_reflns_number_gt                2693
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1042P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6190
_refine_ls_number_parameters     465
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1767
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.2191
_refine_ls_wR_factor_gt          0.1688
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7911(3) 0.3423(3) 0.0738(3) 0.0408(10) Uani 1 1 d . . . . .
C2 C 0.7385(4) 0.2798(3) 0.1500(3) 0.0436(10) Uani 1 1 d . . . . .
C3 C 0.8021(4) 0.2917(4) 0.2623(4) 0.0548(12) Uani 1 1 d . . . . .
H3 H 0.765973 0.250646 0.312773 0.066 Uiso 1 1 calc R U . . .
C4 C 0.9183(4) 0.3638(4) 0.2991(4) 0.0604(13) Uani 1 1 d . . . . .
H4 H 0.961131 0.370843 0.374530 0.073 Uiso 1 1 calc R U . . .
C5 C 0.9722(4) 0.4258(4) 0.2262(4) 0.0605(13) Uani 1 1 d . . . . .
H5 H 1.050904 0.475181 0.251921 0.073 Uiso 1 1 calc R U . . .
C6 C 0.9097(4) 0.4143(4) 0.1161(3) 0.0512(11) Uani 1 1 d . . . . .
H6 H 0.947414 0.456175 0.066996 0.061 Uiso 1 1 calc R U . . .
C7 C 0.7336(4) 0.3369(4) -0.0477(3) 0.0462(11) Uani 1 1 d . . . . .
C8 C 0.5636(4) 0.1442(4) 0.1863(4) 0.0532(12) Uani 1 1 d . . . . .
H11C H 0.561376 0.196885 0.251535 0.064 Uiso 1 1 calc R U . . .
H8B H 0.609999 0.086132 0.212366 0.064 Uiso 1 1 calc R U . . .
C9 C 0.4346(4) 0.0872(4) 0.1219(4) 0.0773(16) Uani 1 1 d . . . . .
H9C H 0.438290 0.037182 0.056505 0.116 Uiso 1 1 calc R U . . .
H9B H 0.389268 0.145873 0.098262 0.116 Uiso 1 1 calc R U . . .
H9A H 0.392630 0.041631 0.169340 0.116 Uiso 1 1 calc R U . . .
C10 C 0.5741(3) 0.3767(3) 0.4966(3) 0.0358(9) Uani 1 1 d . . . . .
C11 C 0.6551(3) 0.4551(3) 0.4532(3) 0.0402(10) Uani 1 1 d . . . . .
H11 H 0.734268 0.491478 0.497188 0.048 Uiso 1 1 calc R U . . .
C12 C 0.6165(3) 0.4780(3) 0.3442(3) 0.0393(10) Uani 1 1 d . . . . .
C13 C 0.4984(3) 0.4245(3) 0.2780(3) 0.0419(10) Uani 1 1 d . . . . .
H13 H 0.472579 0.440524 0.204464 0.050 Uiso 1 1 calc R U . . .
C14 C 0.4195(3) 0.3465(3) 0.3234(3) 0.0392(10) Uani 1 1 d . . . . .
C15 C 0.4558(3) 0.3222(3) 0.4312(3) 0.0382(10) Uani 1 1 d . . . . .
H15 H 0.402001 0.269739 0.460535 0.046 Uiso 1 1 calc R U . . .
C16 C 0.6093(3) 0.3540(3) 0.6148(3) 0.0387(10) Uani 1 1 d . . . . .
C17 C 0.8363(3) -0.0316(3) 0.2820(3) 0.0383(9) Uani 1 1 d . . . . .
C18 C 0.9492(3) 0.0371(3) 0.3468(3) 0.0403(10) Uani 1 1 d . . . . .
H18 H 0.971015 0.038158 0.424966 0.048 Uiso 1 1 calc R U . . .
C19 C 1.0276(3) 0.1031(4) 0.2933(3) 0.0436(10) Uani 1 1 d . . . . .
C20 C 0.9977(4) 0.1036(4) 0.1784(3) 0.0489(11) Uani 1 1 d . . . . .
H20 H 1.052098 0.149366 0.143957 0.059 Uiso 1 1 calc R U . . .
C21 C 0.8846(4) 0.0345(4) 0.1138(3) 0.0465(11) Uani 1 1 d . . . . .
C22 C 0.8052(4) -0.0325(4) 0.1662(3) 0.0460(11) Uani 1 1 d . . . . .
H22 H 0.729906 -0.078794 0.123223 0.055 Uiso 1 1 calc R U . . .
C23 C 0.7548(4) -0.1041(4) 0.3409(4) 0.0443(10) Uani 1 1 d . . . . .
C24 C 0.2026(3) 0.8557(3) 0.3672(3) 0.0368(9) Uani 1 1 d . . . . .
C25 C 0.1630(3) 0.8573(3) 0.2527(3) 0.0394(10) Uani 1 1 d . . . . .
H25 H 0.213494 0.902307 0.214293 0.047 Uiso 1 1 calc R U . . .
C26 C 0.0457(3) 0.7901(3) 0.1951(3) 0.0394(10) Uani 1 1 d . . . . .
C27 C -0.0299(3) 0.7259(3) 0.2525(3) 0.0410(10) Uani 1 1 d . . . . .
H27 H -0.108174 0.681828 0.213589 0.049 Uiso 1 1 calc R U . . .
C28 C 0.0100(3) 0.7265(3) 0.3676(3) 0.0423(10) Uani 1 1 d . . . . .
C29 C 0.1275(3) 0.7909(3) 0.4260(3) 0.0420(10) Uani 1 1 d . . . . .
H29 H 0.155424 0.790544 0.503464 0.050 Uiso 1 1 calc R U . . .
C30 C 0.3306(4) 0.9225(4) 0.4268(3) 0.0428(10) Uani 1 1 d . . . . .
H1A H 0.607(5) 0.214(5) -0.042(5) 0.097(19) Uiso 1 1 d . . . . .
H4A H 0.729(5) 0.407(4) 0.754(5) 0.098(18) Uiso 1 1 d . . . . .
H6A H 0.265(5) 0.260(4) 0.294(4) 0.074(17) Uiso 1 1 d . . . . .
H8A H 0.605(5) -0.190(5) 0.313(5) 0.10(2) Uiso 1 1 d . . . . .
H10A H 0.895(4) 0.078(4) -0.023(4) 0.070(17) Uiso 1 1 d . . . . .
H14A H -0.141(5) 0.628(4) 0.366(4) 0.091(16) Uiso 1 1 d . . . . .
H1B H 0.612(5) 0.244(4) -0.176(5) 0.098(18) Uiso 1 1 d . . . . .
H9D H 1.149(5) 0.159(4) 0.418(5) 0.09(2) Uiso 1 1 d . . . . .
N1 N 0.6350(4) 0.2514(4) -0.0980(4) 0.0670(13) Uani 1 1 d . . . . .
O1 O 0.7769(3) 0.4101(2) -0.1049(2) 0.0577(9) Uani 1 1 d . . . . .
O2 O 0.6214(2) 0.2082(3) 0.1090(2) 0.0541(8) Uani 1 1 d . . . . .
O3 O 0.5446(2) 0.2844(2) 0.6577(2) 0.0529(8) Uani 1 1 d . . . . .
O4 O 0.7191(2) 0.4167(2) 0.6742(3) 0.0480(8) Uani 1 1 d . . . . .
O5 O 0.6969(2) 0.5566(2) 0.3028(2) 0.0574(8) Uani 1 1 d . . . . .
H5A H 0.663570 0.562968 0.237480 0.086 Uiso 1 1 calc R U . . .
O6 O 0.3039(3) 0.2965(3) 0.2539(3) 0.0583(9) Uani 1 1 d . . . . .
O7 O 0.7821(3) -0.1170(3) 0.4386(3) 0.0612(9) Uani 1 1 d . . . . .
O8 O 0.6430(3) -0.1549(3) 0.2739(3) 0.0743(12) Uani 1 1 d . . . . .
O9 O 1.1409(3) 0.1715(3) 0.3522(3) 0.0673(11) Uani 1 1 d . . . . .
O10 O 0.8503(3) 0.0310(3) 0.0002(3) 0.0803(13) Uani 1 1 d . . . . .
O11 O 0.3950(3) 0.9858(3) 0.3751(2) 0.0624(9) Uani 1 1 d . . . . .
O12 O 0.3692(2) 0.9095(2) 0.5304(2) 0.0556(8) Uani 1 1 d . . . . .
H12 H 0.440140 0.949536 0.555648 0.083 Uiso 1 1 calc R U . . .
O13 O 0.0107(2) 0.7922(2) 0.0807(2) 0.0547(8) Uani 1 1 d . . . . .
H13A H -0.059386 0.750501 0.055035 0.082 Uiso 1 1 calc R U . . .
O14 O -0.0613(3) 0.6650(3) 0.4287(2) 0.0670(10) Uani 1 1 d . . . . .
O15 O 0.2100(3) 0.3554(3) 0.0382(2) 0.0581(8) Uani 1 1 d D . . . .
O16 O 0.3961(3) 0.4073(3) 0.9155(3) 0.0898(12) Uani 1 1 d . . . . .
H15A H 0.228(6) 0.323(5) 0.109(3) 0.14(3) Uiso 1 1 d D . . . .
H15B H 0.290(7) 0.382(9) 0.012(10) 0.33(6) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.394(5) . ?
C1 C2 1.397(5) . ?
C1 C7 1.473(5) . ?
C2 O2 1.377(4) . ?
C2 C3 1.382(5) . ?
C3 C4 1.368(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.355(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.251(4) . ?
C7 N1 1.334(5) . ?
C8 O2 1.443(4) . ?
C8 C9 1.481(6) . ?
C8 H11C 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9C 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9A 0.9600 . ?
C10 C15 1.388(5) . ?
C10 C11 1.391(5) . ?
C10 C16 1.474(5) . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 O5 1.373(4) . ?
C12 C13 1.387(5) . ?
C13 C14 1.387(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(5) . ?
C14 O6 1.372(4) . ?
C15 H15 0.9300 . ?
C16 O3 1.219(4) . ?
C16 O4 1.324(4) . ?
C17 C22 1.378(5) . ?
C17 C18 1.392(5) . ?
C17 C23 1.475(5) . ?
C18 C19 1.373(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(5) . ?
C19 O9 1.373(4) . ?
C20 C21 1.395(5) . ?
C20 H20 0.9300 . ?
C21 O10 1.351(5) . ?
C21 C22 1.375(5) . ?
C22 H22 0.9300 . ?
C23 O7 1.197(4) . ?
C23 O8 1.333(5) . ?
C24 C25 1.375(5) . ?
C24 C29 1.386(5) . ?
C24 C30 1.489(5) . ?
C25 C26 1.395(5) . ?
C25 H25 0.9300 . ?
C26 O13 1.370(4) . ?
C26 C27 1.374(5) . ?
C27 C28 1.377(5) . ?
C27 H27 0.9300 . ?
C28 O14 1.361(4) . ?
C28 C29 1.389(5) . ?
C29 H29 0.9300 . ?
C30 O11 1.246(5) . ?
C30 O12 1.277(5) . ?
N1 H1A 0.92(6) . ?
N1 H1B 0.92(6) . ?
O4 H4A 0.98(6) . ?
O5 H5A 0.8200 . ?
O6 H6A 0.82(5) . ?
O8 H8A 0.80(6) . ?
O9 H9D 0.81(6) . ?
O10 H10A 0.78(5) . ?
O12 H12 0.8200 . ?
O13 H13A 0.8200 . ?
O14 H14A 1.03(5) . ?
O15 H15A 0.97(2) . ?
O15 H15B 1.02(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.0(4) . . ?
C6 C1 C7 117.3(3) . . ?
C2 C1 C7 125.8(3) . . ?
O2 C2 C3 122.0(4) . . ?
O2 C2 C1 117.5(3) . . ?
C3 C2 C1 120.5(4) . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 119.3(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 122.5(4) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
O1 C7 N1 119.4(4) . . ?
O1 C7 C1 121.1(4) . . ?
N1 C7 C1 119.5(4) . . ?
O2 C8 C9 106.3(4) . . ?
O2 C8 H11C 110.5 . . ?
C9 C8 H11C 110.5 . . ?
O2 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H11C C8 H8B 108.7 . . ?
C8 C9 H9C 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9C C9 H9B 109.5 . . ?
C8 C9 H9A 109.5 . . ?
H9C C9 H9A 109.5 . . ?
H9B C9 H9A 109.5 . . ?
C15 C10 C11 120.6(3) . . ?
C15 C10 C16 118.4(3) . . ?
C11 C10 C16 120.9(3) . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
O5 C12 C11 118.5(3) . . ?
O5 C12 C13 120.7(3) . . ?
C11 C12 C13 120.9(3) . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 O6 122.5(3) . . ?
C15 C14 C13 121.3(3) . . ?
O6 C14 C13 116.2(3) . . ?
C14 C15 C10 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
O3 C16 O4 120.9(3) . . ?
O3 C16 C10 124.4(3) . . ?
O4 C16 C10 114.7(3) . . ?
C22 C17 C18 120.0(3) . . ?
C22 C17 C23 122.1(3) . . ?
C18 C17 C23 117.9(3) . . ?
C19 C18 C17 118.7(4) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C20 C19 C18 121.9(3) . . ?
C20 C19 O9 116.5(3) . . ?
C18 C19 O9 121.6(4) . . ?
C19 C20 C21 119.1(3) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
O10 C21 C22 118.6(3) . . ?
O10 C21 C20 121.8(3) . . ?
C22 C21 C20 119.6(4) . . ?
C21 C22 C17 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
O7 C23 O8 121.6(4) . . ?
O7 C23 C17 125.4(4) . . ?
O8 C23 C17 113.0(4) . . ?
C25 C24 C29 121.3(3) . . ?
C25 C24 C30 118.4(3) . . ?
C29 C24 C30 120.2(3) . . ?
C24 C25 C26 118.8(3) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
O13 C26 C27 122.5(3) . . ?
O13 C26 C25 117.0(3) . . ?
C27 C26 C25 120.5(3) . . ?
C26 C27 C28 120.2(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
O14 C28 C27 122.6(3) . . ?
O14 C28 C29 117.2(3) . . ?
C27 C28 C29 120.2(3) . . ?
C24 C29 C28 119.0(3) . . ?
C24 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
O11 C30 O12 123.3(3) . . ?
O11 C30 C24 119.9(4) . . ?
O12 C30 C24 116.7(4) . . ?
C7 N1 H1A 108(3) . . ?
C7 N1 H1B 116(3) . . ?
H1A N1 H1B 137(5) . . ?
C2 O2 C8 118.7(3) . . ?
C16 O4 H4A 109(3) . . ?
C12 O5 H5A 109.5 . . ?
C14 O6 H6A 105(4) . . ?
C23 O8 H8A 106(4) . . ?
C19 O9 H9D 106(4) . . ?
C21 O10 H10A 113(4) . . ?
C30 O12 H12 109.5 . . ?
C26 O13 H13A 109.5 . . ?
C28 O14 H14A 101(3) . . ?
H15A O15 H15B 111(7) . . ?

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
C9 H9A O11 0.96 2.65 3.498(6) 147.6 1_545
N1 H1A O2 0.92(6) 1.83(6) 2.652(5) 148(5) .
O4 H4A O1 0.98(6) 1.68(6) 2.644(4) 167(5) 1_556
O6 H6A O9 0.82(5) 1.88(5) 2.678(4) 165(5) 1_455
O8 H8A O3 0.80(6) 1.94(6) 2.682(4) 153(6) 2_656
O10 H10A O13 0.78(5) 1.97(5) 2.745(4) 172(5) 2_665
O14 H14A O5 1.03(5) 1.81(5) 2.800(4) 159(4) 1_455
N1 H1B O3 0.92(6) 2.14(6) 3.020(5) 160(4) 1_554
O9 H9D O7 0.81(6) 1.91(6) 2.689(5) 160(5) 2_756
O5 H5A O16 0.82 1.93 2.746(4) 172.8 2_666
O12 H12 O11 0.82 1.84 2.645(4) 168.9 2_676
O13 H13A O15 0.82 1.95 2.753(4) 166.1 2_565
O15 H15A O6 0.97(2) 1.87(3) 2.816(4) 163(6) .
O15 H15B O16 1.02(2) 1.85(5) 2.824(4) 159(11) 1_554

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_Ethenzamide-35Dihydroxybenzoicacid
_database_code_depnum_ccdc_archive 'CCDC 1504467'
_audit_update_record             
;
2016-12-18 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Ethenzamide-35Dihydroxybenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N O2, C7 H6 O4'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           73
_space_group_name_H-M_alt        'I b c a'
_space_group_name_Hall           '-I 2b 2c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, -z+1/2'
'-x+1/2, y, -z'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, -z+1'
'-x+1, y+1/2, -z+1/2'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'-x, y, z-1/2'
'x-1/2, -y, z'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'x+1/2, y, -z+1/2'

_cell_length_a                   14.9229(8)
_cell_length_b                   18.9781(13)
_cell_length_c                   21.8605(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6191.1(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4300
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.65

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             2688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9822
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13375
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.547
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3322
_reflns_number_gt                2320
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0767P)²+5.1982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3322
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1428
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.86808(15) 0.81411(13) 0.01272(11) 0.0526(6) Uani 1 1 d . . . . .
C2 C 0.87742(16) 0.74687(13) 0.03744(11) 0.0527(6) Uani 1 1 d . . . . .
C3 C 0.87730(19) 0.73760(15) 0.10094(12) 0.0670(7) Uani 1 1 d . . . . .
H3 H 0.884319 0.692595 0.117073 0.080 Uiso 1 1 calc R U . . .
C4 C 0.86715(19) 0.79302(17) 0.13928(14) 0.0716(8) Uani 1 1 d . . . . .
H4 H 0.868066 0.785581 0.181321 0.086 Uiso 1 1 calc R U . . .
C5 C 0.85576(18) 0.85870(17) 0.11748(14) 0.0691(7) Uani 1 1 d . . . . .
H5 H 0.847577 0.896298 0.144194 0.083 Uiso 1 1 calc R U . . .
C6 C 0.85633(17) 0.86978(14) 0.05474(15) 0.0685(8) Uani 1 1 d . . . . .
H6 H 0.848737 0.915322 0.039927 0.082 Uiso 1 1 calc R U . . .
C7 C 0.87260(15) 0.83341(15) -0.05371(13) 0.0596(7) Uani 1 1 d . . . . .
C8 C 0.8925(3) 0.62207(15) 0.02428(16) 0.0866(10) Uani 1 1 d . . . . .
H8A H 0.946225 0.617975 0.049008 0.104 Uiso 1 1 calc R U . . .
H8B H 0.840997 0.612781 0.050113 0.104 Uiso 1 1 calc R U . . .
C9 C 0.8954(4) 0.5725(2) -0.0252(2) 0.1324(17) Uani 1 1 d . . . . .
H9A H 0.840048 0.574447 -0.047532 0.199 Uiso 1 1 calc R U . . .
H9B H 0.903710 0.525871 -0.009118 0.199 Uiso 1 1 calc R U . . .
H9C H 0.944197 0.583978 -0.051943 0.199 Uiso 1 1 calc R U . . .
C10 C 0.75821(11) 0.58388(10) 0.19837(8) 0.0323(4) Uani 1 1 d . . . . .
C11 C 0.80439(11) 0.53014(10) 0.16841(8) 0.0338(4) Uani 1 1 d . . . . .
H11 H 0.773831 0.496405 0.145667 0.041 Uiso 1 1 calc R U . . .
C12 C 0.89703(11) 0.52822(10) 0.17336(8) 0.0324(4) Uani 1 1 d . . . . .
C13 C 0.94230(11) 0.57842(10) 0.20763(8) 0.0340(4) Uani 1 1 d . . . . .
H13 H 1.004490 0.577081 0.210119 0.041 Uiso 1 1 calc R U . . .
C14 C 0.89527(11) 0.63037(10) 0.23807(8) 0.0323(4) Uani 1 1 d . . . . .
C15 C 0.80263(11) 0.63396(10) 0.23316(8) 0.0345(4) Uani 1 1 d . . . . .
H15 H 0.770855 0.669447 0.252913 0.041 Uiso 1 1 calc R U . . .
C16 C 0.65866(12) 0.58871(10) 0.19358(9) 0.0377(5) Uani 1 1 d . . . . .
H1A H 0.8879(19) 0.7867(16) -0.1310(17) 0.072(9) Uiso 1 1 d . . . . .
H4A H 0.564(2) 0.5381(15) 0.1650(12) 0.073(8) Uiso 1 1 d . . . . .
H5A H 0.913(2) 0.4452(16) 0.1234(14) 0.080(9) Uiso 1 1 d . . . . .
H6A H 0.991(2) 0.6676(17) 0.2780(13) 0.097(11) Uiso 1 1 d . . . . .
H1B H 0.891(2) 0.741(2) -0.0855(17) 0.098(13) Uiso 1 1 d . . . . .
N1 N 0.88202(19) 0.78311(19) -0.09414(14) 0.0790(8) Uani 1 1 d . . . . .
O1 O 0.86798(13) 0.89609(11) -0.06850(11) 0.0853(7) Uani 1 1 d . . . . .
O2 O 0.88635(14) 0.69197(9) -0.00143(9) 0.0738(6) Uani 1 1 d . . . . .
O3 O 0.61646(9) 0.64036(9) 0.20869(8) 0.0556(5) Uani 1 1 d . . . . .
O4 O 0.62141(10) 0.53126(9) 0.17155(8) 0.0558(5) Uani 1 1 d . . . . .
O5 O 0.94701(9) 0.47713(8) 0.14565(7) 0.0463(4) Uani 1 1 d . . . . .
O6 O 0.93724(10) 0.67993(8) 0.27337(7) 0.0466(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.393(3) . ?
C1 C6 1.411(4) . ?
C1 C7 1.499(4) . ?
C2 O2 1.351(3) . ?
C2 C3 1.399(3) . ?
C3 C4 1.353(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.345(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.235(3) . ?
C7 N1 1.308(4) . ?
C8 C9 1.433(5) . ?
C8 O2 1.444(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.386(3) . ?
C10 C11 1.394(3) . ?
C10 C16 1.492(2) . ?
C11 C12 1.387(2) . ?
C11 H11 0.9300 . ?
C12 O5 1.365(2) . ?
C12 C13 1.388(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 O6 1.368(2) . ?
C14 C15 1.388(2) . ?
C15 H15 0.9300 . ?
C16 O3 1.211(2) . ?
C16 O4 1.315(2) . ?
N1 H1A 0.81(4) . ?
N1 H1B 0.84(4) . ?
O4 H4A 0.87(3) . ?
O5 H5A 0.93(3) . ?
O6 H6A 0.84(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.5(2) . . ?
C2 C1 C7 126.5(2) . . ?
C6 C1 C7 117.0(2) . . ?
O2 C2 C1 118.2(2) . . ?
O2 C2 C3 121.8(2) . . ?
C1 C2 C3 120.0(2) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 122.1(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
O1 C7 N1 122.1(3) . . ?
O1 C7 C1 119.1(3) . . ?
N1 C7 C1 118.7(2) . . ?
C9 C8 O2 108.1(3) . . ?
C9 C8 H8A 110.1 . . ?
O2 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
O2 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 121.53(16) . . ?
C15 C10 C16 118.20(16) . . ?
C11 C10 C16 120.27(16) . . ?
C12 C11 C10 118.36(17) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
O5 C12 C11 121.91(16) . . ?
O5 C12 C13 117.47(15) . . ?
C11 C12 C13 120.62(16) . . ?
C14 C13 C12 120.19(16) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O6 C14 C13 121.99(15) . . ?
O6 C14 C15 117.75(16) . . ?
C13 C14 C15 120.26(16) . . ?
C10 C15 C14 119.02(16) . . ?
C10 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
O3 C16 O4 123.44(17) . . ?
O3 C16 C10 123.26(18) . . ?
O4 C16 C10 113.31(17) . . ?
C7 N1 H1A 128(2) . . ?
C7 N1 H1B 124(3) . . ?
H1A N1 H1B 107(3) . . ?
C2 O2 C8 118.0(2) . . ?
C16 O4 H4A 110.5(19) . . ?
C12 O5 H5A 113.6(18) . . ?
C14 O6 H6A 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
N1 H1A O6 0.81(4) 2.31(4) 3.092(3) 163(3) 15_564
O4 H4A O5 0.87(3) 1.83(3) 2.6681(19) 162(3) 11_565
O5 H5A O1 0.93(3) 1.66(3) 2.569(2) 165(3) 12
O6 H6A O3 0.84(4) 1.97(4) 2.805(2) 178(3) 16
N1 H1B O2 0.84(4) 2.06(4) 2.665(3) 129(3) .

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_Ethenzamide-Ferulicacid
_database_code_depnum_ccdc_archive 'CCDC 1504468'
_audit_update_record             
;
2016-12-18 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Ethenzamide Ferulic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 O4, C9 H11 N O2'
_chemical_formula_sum            'C19 H21 N O6'
_chemical_formula_weight         359.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   15.539(2)
_cell_length_b                   7.4265(10)
_cell_length_c                   31.796(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3669.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2486
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      20.96

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28799
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.281
_diffrn_reflns_theta_max         26.437
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3757
_reflns_number_gt                2078
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0783P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3757
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1617
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.28318(14) 0.0948(3) 0.26490(7) 0.0419(5) Uani 1 1 d . . . . .
C2 C 0.19297(15) 0.0921(3) 0.26440(8) 0.0463(6) Uani 1 1 d . . . . .
C3 C 0.14931(17) 0.1479(3) 0.22874(8) 0.0567(7) Uani 1 1 d . . . . .
H3 H 0.089469 0.146037 0.228342 0.068 Uiso 1 1 calc R U . . .
C4 C 0.19369(19) 0.2057(3) 0.19401(9) 0.0613(7) Uani 1 1 d . . . . .
H4 H 0.163551 0.242329 0.170233 0.074 Uiso 1 1 calc R U . . .
C5 C 0.28176(18) 0.2104(3) 0.19387(8) 0.0567(7) Uani 1 1 d . . . . .
H5 H 0.311705 0.250369 0.170328 0.068 Uiso 1 1 calc R U . . .
C6 C 0.32497(16) 0.1546(3) 0.22929(7) 0.0507(6) Uani 1 1 d . . . . .
H6 H 0.384810 0.157331 0.229220 0.061 Uiso 1 1 calc R U . . .
C7 C 0.33835(15) 0.0374(3) 0.30074(7) 0.0451(6) Uani 1 1 d . . . . .
C8 C 0.05958(16) 0.0359(4) 0.30168(10) 0.0689(8) Uani 1 1 d . . . . .
H8A H 0.035336 -0.042093 0.280274 0.083 Uiso 1 1 calc R U . . .
H8B H 0.038825 0.157430 0.296929 0.083 Uiso 1 1 calc R U . . .
C9 C 0.03371(18) -0.0275(4) 0.34442(11) 0.0843(10) Uani 1 1 d . . . . .
H9A H 0.051745 -0.150069 0.348161 0.126 Uiso 1 1 calc R U . . .
H9B H -0.027706 -0.020038 0.347202 0.126 Uiso 1 1 calc R U . . .
H9C H 0.060461 0.046912 0.365365 0.126 Uiso 1 1 calc R U . . .
C10 C 0.73079(14) 0.8992(3) 0.44333(7) 0.0411(6) Uani 1 1 d . . . . .
C11 C 0.71442(14) 0.8393(3) 0.48426(7) 0.0447(6) Uani 1 1 d . . . . .
H11 H 0.657935 0.823922 0.493236 0.054 Uiso 1 1 calc R U . . .
C12 C 0.78062(14) 0.8032(3) 0.51108(7) 0.0477(6) Uani 1 1 d . . . . .
C13 C 0.86553(14) 0.8255(4) 0.49800(8) 0.0550(7) Uani 1 1 d . . . . .
C14 C 0.88213(15) 0.8885(4) 0.45836(8) 0.0586(7) Uani 1 1 d . . . . .
H14 H 0.938639 0.907157 0.449759 0.070 Uiso 1 1 calc R U . . .
C15 C 0.81516(15) 0.9243(3) 0.43119(7) 0.0489(6) Uani 1 1 d . . . . .
H15 H 0.827050 0.966031 0.404231 0.059 Uiso 1 1 calc R U . . .
C16 C 0.66088(14) 0.9310(3) 0.41395(7) 0.0429(6) Uani 1 1 d . . . . .
H16 H 0.675517 0.982338 0.388244 0.052 Uiso 1 1 calc R U . . .
C17 C 0.57881(15) 0.8946(4) 0.42000(7) 0.0521(6) Uani 1 1 d . . . . .
H17 H 0.563580 0.845411 0.445848 0.063 Uiso 1 1 calc R U . . .
C18 C 0.51004(15) 0.9246(3) 0.38987(7) 0.0479(6) Uani 1 1 d . . . . .
C19 C 0.68800(18) 0.7275(5) 0.56843(8) 0.0725(8) Uani 1 1 d . . . . .
H19A H 0.659257 0.841740 0.566890 0.109 Uiso 1 1 calc R U . . .
H19B H 0.691101 0.689257 0.597226 0.109 Uiso 1 1 calc R U . . .
H19C H 0.656530 0.640114 0.552352 0.109 Uiso 1 1 calc R U . . .
H1A H 0.251(2) -0.022(4) 0.3376(9) 0.080(10) Uiso 1 1 d . . . . .
H3A H 0.488(2) 1.005(4) 0.3372(11) 0.104(11) Uiso 1 1 d . . . . .
H6A H 0.915(3) 0.751(6) 0.5471(14) 0.136(17) Uiso 1 1 d . . . . .
H1B H 0.3373(19) -0.048(4) 0.3579(9) 0.075(9) Uiso 1 1 d . . . . .
N1 N 0.30316(17) -0.0174(4) 0.33606(7) 0.0663(7) Uani 1 1 d . . . . .
O1 O 0.41786(10) 0.0416(3) 0.29703(5) 0.0630(5) Uani 1 1 d . . . . .
O2 O 0.15198(10) 0.0318(2) 0.29979(5) 0.0575(5) Uani 1 1 d . . . . .
O3 O 0.53478(11) 0.9863(3) 0.35308(6) 0.0642(6) Uani 1 1 d . . . . .
O4 O 0.43481(10) 0.8915(3) 0.39771(5) 0.0654(6) Uani 1 1 d . . . . .
O5 O 0.77233(11) 0.7444(3) 0.55190(5) 0.0652(5) Uani 1 1 d . . . . .
O6 O 0.93221(12) 0.7894(3) 0.52427(8) 0.0875(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.379(3) . ?
C1 C2 1.402(3) . ?
C1 C7 1.488(3) . ?
C2 O2 1.368(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.242(3) . ?
C7 N1 1.314(3) . ?
C8 O2 1.437(3) . ?
C8 C9 1.493(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.379(3) . ?
C10 C11 1.399(3) . ?
C10 C16 1.452(3) . ?
C11 C12 1.363(3) . ?
C11 H11 0.9300 . ?
C12 O5 1.376(3) . ?
C12 C13 1.393(3) . ?
C13 O6 1.358(3) . ?
C13 C14 1.369(3) . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.318(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.452(3) . ?
C17 H17 0.9300 . ?
C18 O4 1.220(3) . ?
C18 O3 1.314(3) . ?
C19 O5 1.417(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 H1A 0.81(3) . ?
N1 H1B 0.90(3) . ?
O3 H3A 0.89(4) . ?
O6 H6A 0.83(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.8(2) . . ?
C6 C1 C7 116.7(2) . . ?
C2 C1 C7 125.5(2) . . ?
O2 C2 C3 122.9(2) . . ?
O2 C2 C1 117.4(2) . . ?
C3 C2 C1 119.7(2) . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 122.7(2) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
O1 C7 N1 120.2(2) . . ?
O1 C7 C1 119.6(2) . . ?
N1 C7 C1 120.2(2) . . ?
O2 C8 C9 107.5(2) . . ?
O2 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
O2 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.4(2) . . ?
C15 C10 C16 120.6(2) . . ?
C11 C10 C16 121.0(2) . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 O5 125.6(2) . . ?
C11 C12 C13 120.3(2) . . ?
O5 C12 C13 114.1(2) . . ?
O6 C13 C14 119.3(2) . . ?
O6 C13 C12 121.0(2) . . ?
C14 C13 C12 119.6(2) . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C17 C16 C10 126.6(2) . . ?
C17 C16 H16 116.7 . . ?
C10 C16 H16 116.7 . . ?
C16 C17 C18 125.7(2) . . ?
C16 C17 H17 117.1 . . ?
C18 C17 H17 117.1 . . ?
O4 C18 O3 122.2(2) . . ?
O4 C18 C17 122.6(2) . . ?
O3 C18 C17 115.2(2) . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 N1 H1A 119(2) . . ?
C7 N1 H1B 119.4(18) . . ?
H1A N1 H1B 122(3) . . ?
C2 O2 C8 119.5(2) . . ?
C18 O3 H3A 109(2) . . ?
C12 O5 C19 117.67(19) . . ?
C13 O6 H6A 111(3) . . ?

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
C17 H17 O6 0.93 2.46 3.193(3) 135.3 2_466
N1 H1A O2 0.81(3) 2.00(3) 2.642(3) 137(3) .
O3 H3A O1 0.89(4) 1.70(4) 2.578(2) 166(3) 1_565
O6 H6A O4 0.83(4) 2.07(4) 2.821(3) 150(4) 2_566
O6 H6A O5 0.83(4) 2.21(4) 2.656(3) 114(4) .
N1 H1B O4 0.90(3) 2.02(3) 2.913(3) 168(2) 1_545

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.052

