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

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

data_PB_form_V
_database_code_depnum_ccdc_archive 'CCDC 1450610'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            Phenobarbital
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2 O3'
_chemical_formula_sum            'C12 H12 N2 O3'
_chemical_formula_weight         232.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   13.0764(3)
_cell_length_b                   6.72680(10)
_cell_length_c                   26.5912(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.083(7)
_cell_angle_gamma                90.00
_cell_volume                     2309.69(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    85(2)
_cell_measurement_reflns_used    10528
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8948
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      85(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'micro-focus Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21487
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         68.22
_reflns_number_total             4150
_reflns_number_gt                2889
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4150
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0876
_refine_ls_wR_factor_ref         0.2379
_refine_ls_wR_factor_gt          0.2194
_refine_ls_goodness_of_fit_ref   1.401
_refine_ls_restrained_S_all      1.401
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50810(19) 1.3150(4) 0.09576(8) 0.0423(6) Uani 1 1 d . . .
O2 O 0.72861(18) 0.8934(3) -0.06917(8) 0.0392(6) Uani 1 1 d . . .
O3 O 0.4486(2) 1.3205(4) 0.25872(9) 0.0454(7) Uani 1 1 d . . .
O4 O 0.50976(18) 0.8123(3) 0.04396(8) 0.0374(6) Uani 1 1 d . . .
O5 O 0.72099(19) 0.3039(4) 0.02008(9) 0.0465(7) Uani 1 1 d . . .
O6 O 0.4920(2) 0.7217(4) 0.17108(9) 0.0519(7) Uani 1 1 d . . .
N7 N 0.5048(2) 1.0192(4) 0.13595(10) 0.0340(7) Uani 1 1 d . . .
H7 H 0.5192 0.9591 0.1085 0.041 Uiso 1 1 calc R . .
N10 N 0.6329(2) 0.8673(4) -0.00583(9) 0.0321(6) Uani 1 1 d . . .
H10 H 0.6136 0.9924 -0.0097 0.039 Uiso 1 1 calc R . .
N11 N 0.6214(2) 0.5642(4) 0.03452(10) 0.0346(7) Uani 1 1 d . . .
H11 H 0.5898 0.4895 0.0545 0.042 Uiso 1 1 calc R . .
N12 N 0.4809(2) 1.3143(4) 0.17796(10) 0.0355(7) Uani 1 1 d . . .
H12 H 0.4777 1.4449 0.1774 0.043 Uiso 1 1 calc R . .
C8 C 0.4988(3) 1.2219(5) 0.13427(12) 0.0344(8) Uani 1 1 d . . .
C9 C 0.4907(3) 0.9009(5) 0.17578(12) 0.0338(8) Uani 1 1 d . . .
C13 C 0.7037(3) 0.4792(5) 0.01484(12) 0.0337(8) Uani 1 1 d . . .
C14 C 0.4674(3) 1.2220(5) 0.22289(12) 0.0359(8) Uani 1 1 d . . .
C15 C 0.7097(3) 0.8011(5) -0.03233(12) 0.0325(8) Uani 1 1 d . . .
C16 C 0.7718(3) 0.6240(5) -0.00961(12) 0.0338(8) Uani 1 1 d . . .
C17 C 0.8551(2) 0.7037(5) 0.03330(11) 0.0323(8) Uani 1 1 d . . .
C18 C 0.5855(3) 0.7526(5) 0.02552(11) 0.0315(7) Uani 1 1 d . . .
C19 C 0.4755(3) 0.9986(5) 0.22590(12) 0.0346(8) Uani 1 1 d . . .
C20 C 0.5698(3) 0.9401(6) 0.26546(12) 0.0391(8) Uani 1 1 d . . .
C21 C 0.8236(3) 0.5153(5) -0.05020(13) 0.0389(8) Uani 1 1 d . . .
H21A H 0.8708 0.6091 -0.0638 0.047 Uiso 1 1 calc R . .
H21B H 0.8662 0.4049 -0.0336 0.047 Uiso 1 1 calc R . .
C22 C 0.6557(3) 1.0638(6) 0.27546(14) 0.0467(9) Uani 1 1 d . . .
H22 H 0.6567 1.1865 0.2579 0.056 Uiso 1 1 calc R . .
C23 C 0.3718(3) 0.9213(6) 0.23963(13) 0.0421(9) Uani 1 1 d . . .
H23A H 0.3734 0.7742 0.2406 0.050 Uiso 1 1 calc R . .
H23B H 0.3645 0.9690 0.2741 0.050 Uiso 1 1 calc R . .
C24 C 0.6564(3) 0.7042(6) 0.32613(14) 0.0497(10) Uani 1 1 d . . .
H24 H 0.6569 0.5799 0.3432 0.060 Uiso 1 1 calc R . .
C25 C 0.8970(3) 0.5840(7) 0.07363(14) 0.0504(10) Uani 1 1 d . . .
H25 H 0.8733 0.4510 0.0752 0.060 Uiso 1 1 calc R . .
C26 C 0.5728(3) 0.7581(6) 0.29063(13) 0.0447(9) Uani 1 1 d . . .
H26 H 0.5160 0.6693 0.2831 0.054 Uiso 1 1 calc R . .
C27 C 0.7477(3) 0.4317(6) -0.09445(13) 0.0466(9) Uani 1 1 d . . .
H27A H 0.7862 0.3659 -0.1185 0.056 Uiso 1 1 calc R . .
H27B H 0.7062 0.5402 -0.1117 0.056 Uiso 1 1 calc R . .
H27C H 0.7020 0.3352 -0.0816 0.056 Uiso 1 1 calc R . .
C28 C 0.2780(3) 0.9884(6) 0.20212(13) 0.0450(9) Uani 1 1 d . . .
H28A H 0.2148 0.9359 0.2127 0.054 Uiso 1 1 calc R . .
H28B H 0.2838 0.9387 0.1680 0.054 Uiso 1 1 calc R . .
H28C H 0.2751 1.1340 0.2015 0.054 Uiso 1 1 calc R . .
C29 C 0.7391(3) 0.8314(7) 0.33672(15) 0.0552(11) Uani 1 1 d . . .
H29 H 0.7959 0.7965 0.3620 0.066 Uiso 1 1 calc R . .
C30 C 1.0078(3) 0.8459(8) 0.11007(15) 0.0586(12) Uani 1 1 d . . .
H30 H 1.0592 0.8949 0.1364 0.070 Uiso 1 1 calc R . .
C31 C 0.9722(3) 0.6538(8) 0.11149(14) 0.0592(12) Uani 1 1 d . . .
H31 H 0.9998 0.5688 0.1388 0.071 Uiso 1 1 calc R . .
C32 C 0.8904(4) 0.8968(6) 0.03245(18) 0.0636(13) Uani 1 1 d . . .
H32 H 0.8615 0.9836 0.0058 0.076 Uiso 1 1 calc R . .
C33 C 0.9677(4) 0.9651(7) 0.07007(19) 0.0725(14) Uani 1 1 d . . .
H33 H 0.9933 1.0965 0.0681 0.087 Uiso 1 1 calc R . .
C34 C 0.7406(3) 1.0075(7) 0.31140(15) 0.0541(11) Uani 1 1 d . . .
H34 H 0.7994 1.0919 0.3182 0.065 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.223(4) . ?
O2 C15 1.218(4) . ?
O3 C14 1.217(4) . ?
O4 C18 1.240(4) . ?
O5 C13 1.204(4) . ?
O6 C9 1.212(4) . ?
N7 C9 1.361(4) . ?
N7 C8 1.366(4) . ?
N7 H7 0.8800 . ?
N10 C18 1.355(4) . ?
N10 C15 1.388(4) . ?
N10 H10 0.8800 . ?
N11 C18 1.359(4) . ?
N11 C13 1.392(4) . ?
N11 H11 0.8800 . ?
N12 C8 1.370(4) . ?
N12 C14 1.382(4) . ?
N12 H12 0.8800 . ?
C9 C19 1.527(4) . ?
C13 C16 1.532(5) . ?
C14 C19 1.508(5) . ?
C15 C16 1.513(5) . ?
C16 C17 1.544(4) . ?
C16 C21 1.546(4) . ?
C17 C32 1.380(5) . ?
C17 C25 1.383(5) . ?
C19 C20 1.540(5) . ?
C19 C23 1.549(5) . ?
C20 C22 1.390(5) . ?
C20 C26 1.393(5) . ?
C21 C27 1.522(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C34 1.398(5) . ?
C22 H22 0.9500 . ?
C23 C28 1.522(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C29 1.373(6) . ?
C24 C26 1.375(5) . ?
C24 H24 0.9500 . ?
C25 C31 1.374(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C34 1.364(6) . ?
C29 H29 0.9500 . ?
C30 C33 1.368(6) . ?
C30 C31 1.376(6) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.383(6) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N7 C8 126.5(3) . . ?
C9 N7 H7 116.7 . . ?
C8 N7 H7 116.7 . . ?
C18 N10 C15 124.6(3) . . ?
C18 N10 H10 117.7 . . ?
C15 N10 H10 117.7 . . ?
C18 N11 C13 125.6(3) . . ?
C18 N11 H11 117.2 . . ?
C13 N11 H11 117.2 . . ?
C8 N12 C14 126.3(3) . . ?
C8 N12 H12 116.9 . . ?
C14 N12 H12 116.9 . . ?
O1 C8 N7 121.8(3) . . ?
O1 C8 N12 122.0(3) . . ?
N7 C8 N12 116.2(3) . . ?
O6 C9 N7 119.7(3) . . ?
O6 C9 C19 121.6(3) . . ?
N7 C9 C19 118.7(3) . . ?
O5 C13 N11 120.0(3) . . ?
O5 C13 C16 124.1(3) . . ?
N11 C13 C16 115.7(3) . . ?
O3 C14 N12 120.1(3) . . ?
O3 C14 C19 121.5(3) . . ?
N12 C14 C19 118.4(3) . . ?
O2 C15 N10 120.0(3) . . ?
O2 C15 C16 123.9(3) . . ?
N10 C15 C16 115.8(3) . . ?
C15 C16 C13 111.0(3) . . ?
C15 C16 C17 107.0(3) . . ?
C13 C16 C17 107.3(2) . . ?
C15 C16 C21 111.1(3) . . ?
C13 C16 C21 110.1(3) . . ?
C17 C16 C21 110.1(3) . . ?
C32 C17 C25 117.9(3) . . ?
C32 C17 C16 120.9(3) . . ?
C25 C17 C16 121.2(3) . . ?
O4 C18 N10 122.0(3) . . ?
O4 C18 N11 120.5(3) . . ?
N10 C18 N11 117.4(3) . . ?
C14 C19 C9 113.6(3) . . ?
C14 C19 C20 109.4(3) . . ?
C9 C19 C20 106.6(3) . . ?
C14 C19 C23 106.9(3) . . ?
C9 C19 C23 107.5(3) . . ?
C20 C19 C23 112.9(3) . . ?
C22 C20 C26 118.2(3) . . ?
C22 C20 C19 120.9(3) . . ?
C26 C20 C19 120.8(3) . . ?
C27 C21 C16 114.2(3) . . ?
C27 C21 H21A 108.7 . . ?
C16 C21 H21A 108.7 . . ?
C27 C21 H21B 108.7 . . ?
C16 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C20 C22 C34 120.0(4) . . ?
C20 C22 H22 120.0 . . ?
C34 C22 H22 120.0 . . ?
C28 C23 C19 113.0(3) . . ?
C28 C23 H23A 109.0 . . ?
C19 C23 H23A 109.0 . . ?
C28 C23 H23B 109.0 . . ?
C19 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C29 C24 C26 119.4(4) . . ?
C29 C24 H24 120.3 . . ?
C26 C24 H24 120.3 . . ?
C31 C25 C17 121.3(4) . . ?
C31 C25 H25 119.4 . . ?
C17 C25 H25 119.4 . . ?
C24 C26 C20 121.4(4) . . ?
C24 C26 H26 119.3 . . ?
C20 C26 H26 119.3 . . ?
C21 C27 H27A 109.5 . . ?
C21 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C21 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C34 C29 C24 120.9(4) . . ?
C34 C29 H29 119.6 . . ?
C24 C29 H29 119.6 . . ?
C33 C30 C31 118.8(4) . . ?
C33 C30 H30 120.6 . . ?
C31 C30 H30 120.6 . . ?
C25 C31 C30 120.4(4) . . ?
C25 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C17 C32 C33 120.6(4) . . ?
C17 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C30 C33 C32 120.9(4) . . ?
C30 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C29 C34 C22 120.0(4) . . ?
C29 C34 H34 120.0 . . ?
C22 C34 H34 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N7 C8 O1 -176.6(3) . . . . ?
C9 N7 C8 N12 2.8(5) . . . . ?
C14 N12 C8 O1 178.7(3) . . . . ?
C14 N12 C8 N7 -0.7(5) . . . . ?
C8 N7 C9 O6 175.6(3) . . . . ?
C8 N7 C9 C19 -5.6(5) . . . . ?
C18 N11 C13 O5 -170.8(3) . . . . ?
C18 N11 C13 C16 13.2(4) . . . . ?
C8 N12 C14 O3 -177.6(3) . . . . ?
C8 N12 C14 C19 1.7(5) . . . . ?
C18 N10 C15 O2 160.4(3) . . . . ?
C18 N10 C15 C16 -24.9(4) . . . . ?
O2 C15 C16 C13 -150.0(3) . . . . ?
N10 C15 C16 C13 35.6(4) . . . . ?
O2 C15 C16 C17 93.2(4) . . . . ?
N10 C15 C16 C17 -81.2(3) . . . . ?
O2 C15 C16 C21 -27.1(4) . . . . ?
N10 C15 C16 C21 158.5(3) . . . . ?
O5 C13 C16 C15 154.1(3) . . . . ?
N11 C13 C16 C15 -30.1(4) . . . . ?
O5 C13 C16 C17 -89.3(4) . . . . ?
N11 C13 C16 C17 86.5(3) . . . . ?
O5 C13 C16 C21 30.5(4) . . . . ?
N11 C13 C16 C21 -153.6(3) . . . . ?
C15 C16 C17 C32 -25.8(4) . . . . ?
C13 C16 C17 C32 -145.0(4) . . . . ?
C21 C16 C17 C32 95.1(4) . . . . ?
C15 C16 C17 C25 154.5(3) . . . . ?
C13 C16 C17 C25 35.3(4) . . . . ?
C21 C16 C17 C25 -84.6(4) . . . . ?
C15 N10 C18 O4 -172.0(3) . . . . ?
C15 N10 C18 N11 5.2(4) . . . . ?
C13 N11 C18 O4 178.2(3) . . . . ?
C13 N11 C18 N10 0.9(4) . . . . ?
O3 C14 C19 C9 175.2(3) . . . . ?
N12 C14 C19 C9 -4.1(4) . . . . ?
O3 C14 C19 C20 -65.8(4) . . . . ?
N12 C14 C19 C20 114.9(3) . . . . ?
O3 C14 C19 C23 56.8(4) . . . . ?
N12 C14 C19 C23 -122.5(3) . . . . ?
O6 C9 C19 C14 -175.3(3) . . . . ?
N7 C9 C19 C14 5.8(4) . . . . ?
O6 C9 C19 C20 64.1(4) . . . . ?
N7 C9 C19 C20 -114.7(3) . . . . ?
O6 C9 C19 C23 -57.2(4) . . . . ?
N7 C9 C19 C23 123.9(3) . . . . ?
C14 C19 C20 C22 -28.7(4) . . . . ?
C9 C19 C20 C22 94.5(4) . . . . ?
C23 C19 C20 C22 -147.6(3) . . . . ?
C14 C19 C20 C26 154.0(3) . . . . ?
C9 C19 C20 C26 -82.8(4) . . . . ?
C23 C19 C20 C26 35.0(4) . . . . ?
C15 C16 C21 C27 -61.2(4) . . . . ?
C13 C16 C21 C27 62.2(4) . . . . ?
C17 C16 C21 C27 -179.7(3) . . . . ?
C26 C20 C22 C34 -2.4(5) . . . . ?
C19 C20 C22 C34 -179.8(3) . . . . ?
C14 C19 C23 C28 56.5(4) . . . . ?
C9 C19 C23 C28 -65.8(4) . . . . ?
C20 C19 C23 C28 176.9(3) . . . . ?
C32 C17 C25 C31 -0.7(6) . . . . ?
C16 C17 C25 C31 179.1(3) . . . . ?
C29 C24 C26 C20 -0.6(6) . . . . ?
C22 C20 C26 C24 2.7(5) . . . . ?
C19 C20 C26 C24 -179.8(3) . . . . ?
C26 C24 C29 C34 -2.0(6) . . . . ?
C17 C25 C31 C30 0.0(6) . . . . ?
C33 C30 C31 C25 -0.7(7) . . . . ?
C25 C17 C32 C33 2.0(7) . . . . ?
C16 C17 C32 C33 -177.7(4) . . . . ?
C31 C30 C33 C32 2.1(7) . . . . ?
C17 C32 C33 C30 -2.8(8) . . . . ?
C24 C29 C34 C22 2.4(6) . . . . ?
C20 C22 C34 C29 -0.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        68.22
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.098
_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_PB_form_XV
_database_code_depnum_ccdc_archive 'CCDC 1450611'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            Phenobarbital
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2 O3'
_chemical_formula_sum            'C12 H12 N2 O3'
_chemical_formula_weight         232.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   14.5744(4)
_cell_length_b                   6.88000(19)
_cell_length_c                   22.9964(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.987(7)
_cell_angle_gamma                90.00
_cell_volume                     2300.31(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    95(2)
_cell_measurement_reflns_used    5246
_cell_measurement_theta_min      6.7
_cell_measurement_theta_max      54.2

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9439
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_process_details   
; 
 T. Higashi, (1995). Program for Absorption Correction.
 Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
; 
 T. Higashi, (1995). Program for Absorption Correction.
 Rigaku Corporation, Tokyo, Japan.
;

_diffrn_ambient_temperature      95(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'rigaku RAXIS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9546
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1185
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         6.72
_diffrn_reflns_theta_max         54.24
_reflns_number_total             2768
_reflns_number_gt                1260
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'Crystal Structure 3.8'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'Crystal Structure 3.8'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0003P)²+16.1750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       0.00145(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2768
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1831
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.2328
_refine_ls_wR_factor_gt          0.1570
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.171
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7340(2) -0.1309(5) 1.13091(18) 0.0363(12) Uani 1 1 d . . .
O2 O 0.7733(2) 0.4668(5) 1.05568(16) 0.0425(12) Uani 1 1 d . . .
O3 O 0.4548(3) -0.2893(5) 0.63800(19) 0.0484(13) Uani 1 1 d . . .
O4 O 0.4303(2) -0.1890(5) 0.83723(19) 0.0395(12) Uani 1 1 d . . .
O5 O 0.2587(2) 0.1577(5) 0.70316(17) 0.0407(12) Uani 1 1 d . . .
O7 O 0.7811(3) -0.0986(5) 0.9387(2) 0.0510(14) Uani 1 1 d . . .
N1 N 0.3633(3) -0.0536(6) 0.6709(2) 0.0398(14) Uani 1 1 d . . .
H23 H 0.3437 -0.0274 0.6357 0.048 Uiso 1 1 calc R . .
N7 N 0.3538(3) -0.0010(6) 0.7706(2) 0.0350(13) Uani 1 1 d . . .
H22 H 0.3295 0.0611 0.7981 0.042 Uiso 1 1 calc R . .
N9 N 0.7491(3) 0.1714(6) 1.0923(2) 0.0378(14) Uani 1 1 d . . .
H18 H 0.7413 0.2235 1.1256 0.045 Uiso 1 1 calc R . .
N10 N 0.7576(3) -0.1107(6) 1.0345(2) 0.0384(14) Uani 1 1 d . . .
H19 H 0.7583 -0.2355 1.0326 0.046 Uiso 1 1 calc R . .
C11 C 0.7576(4) 0.2123(7) 0.9851(3) 0.0337(17) Uani 1 1 d . . .
C12 C 0.4833(4) -0.1958(7) 0.7387(3) 0.0314(16) Uani 1 1 d . . .
C13 C 0.7665(4) -0.0103(8) 0.9825(4) 0.043(2) Uani 1 1 d . . .
C14 C 0.7477(4) -0.0303(9) 1.0884(3) 0.0344(17) Uani 1 1 d . . .
C15 C 0.3230(4) 0.0432(9) 0.7156(3) 0.0339(17) Uani 1 1 d . . .
C16 C 0.7622(4) 0.2920(10) 1.0461(3) 0.0383(17) Uani 1 1 d . . .
C17 C 0.5915(4) 0.0401(8) 0.6908(3) 0.0424(18) Uani 1 1 d . . .
H24 H 0.5652 0.0032 0.6545 0.051 Uiso 1 1 calc R . .
C18 C 0.8365(4) 0.2969(7) 0.9522(3) 0.0406(17) Uani 1 1 d . . .
H16 H 0.8294 0.4369 0.9495 0.049 Uiso 1 1 calc R . .
H17 H 0.8332 0.2450 0.9129 0.049 Uiso 1 1 calc R . .
C19 C 0.6747(4) 0.1460(8) 0.8004(3) 0.0419(18) Uani 1 1 d . . .
H1 H 0.7023 0.1820 0.8365 0.050 Uiso 1 1 calc R . .
C20 C 0.5627(4) -0.0420(8) 0.7423(3) 0.0346(16) Uani 1 1 d . . .
C21 C 0.6621(4) 0.1815(8) 0.6963(3) 0.0456(19) Uani 1 1 d . . .
H2 H 0.6809 0.2439 0.6633 0.055 Uiso 1 1 calc R . .
C22 C 0.4865(4) 0.3791(10) 0.9138(3) 0.0501(19) Uani 1 1 d . . .
H3 H 0.4282 0.4168 0.8990 0.060 Uiso 1 1 calc R . .
C23 C 0.6041(4) 0.0096(8) 0.7963(3) 0.0412(18) Uani 1 1 d . . .
H4 H 0.5846 -0.0474 0.8299 0.049 Uiso 1 1 calc R . .
C24 C 0.4344(4) -0.1923(9) 0.6796(3) 0.0387(18) Uani 1 1 d . . .
C25 C 0.5892(4) 0.1334(8) 0.9526(3) 0.0408(17) Uani 1 1 d . . .
H5 H 0.5994 0.0054 0.9644 0.049 Uiso 1 1 calc R . .
C26 C 0.4215(4) -0.1381(8) 0.7874(3) 0.0407(19) Uani 1 1 d . . .
C27 C 0.6608(4) 0.2659(9) 0.9578(3) 0.0420(18) Uani 1 1 d . . .
C28 C 0.5242(3) -0.3975(7) 0.7519(3) 0.0427(18) Uani 1 1 d . . .
H20 H 0.5569 -0.3955 0.7901 0.051 Uiso 1 1 calc R . .
H21 H 0.5683 -0.4274 0.7235 0.051 Uiso 1 1 calc R . .
C29 C 0.7027(4) 0.2265(8) 0.7497(3) 0.0429(18) Uani 1 1 d . . .
H6 H 0.7511 0.3149 0.7521 0.051 Uiso 1 1 calc R . .
C30 C 0.6431(4) 0.4604(8) 0.9408(3) 0.0440(18) Uani 1 1 d . . .
H7 H 0.6901 0.5520 0.9443 0.053 Uiso 1 1 calc R . .
C31 C 0.5025(4) 0.1894(9) 0.9299(3) 0.054(2) Uani 1 1 d . . .
H8 H 0.4552 0.0985 0.9256 0.065 Uiso 1 1 calc R . .
C32 C 0.5567(5) 0.5142(9) 0.9193(3) 0.054(2) Uani 1 1 d . . .
H9 H 0.5452 0.6426 0.9084 0.064 Uiso 1 1 calc R . .
C33 C 0.4505(3) -0.5598(7) 0.7505(3) 0.0504(19) Uani 1 1 d . . .
H10 H 0.4280 -0.5736 0.7885 0.060 Uiso 1 1 calc R . .
H11 H 0.4772 -0.6802 0.7391 0.060 Uiso 1 1 calc R . .
H12 H 0.4004 -0.5260 0.7230 0.060 Uiso 1 1 calc R . .
C34 C 0.9319(4) 0.2493(7) 0.9826(3) 0.060(2) Uani 1 1 d . . .
H13 H 0.9504 0.3523 1.0091 0.072 Uiso 1 1 calc R . .
H14 H 0.9761 0.2362 0.9538 0.072 Uiso 1 1 calc R . .
H15 H 0.9284 0.1297 1.0039 0.072 Uiso 1 1 calc R . .


_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 C14 1.226(6) . ?
O2 C16 1.232(6) . ?
O3 C24 1.220(6) . ?
O4 C26 1.197(7) . ?
O5 C15 1.242(6) . ?
O7 C13 1.207(7) . ?
N1 C15 1.387(6) . ?
N1 C24 1.413(6) . ?
N7 C15 1.348(6) . ?
N7 C26 1.400(6) . ?
N9 C16 1.373(6) . ?
N9 C14 1.391(6) . ?
N10 C14 1.375(7) . ?
N10 C13 1.394(7) . ?
C11 C16 1.502(7) . ?
C11 C18 1.534(6) . ?
C11 C13 1.539(7) . ?
C11 C27 1.549(7) . ?
C12 C24 1.491(7) . ?
C12 C28 1.532(6) . ?
C12 C26 1.538(8) . ?
C12 C20 1.566(7) . ?
C17 C20 1.403(7) . ?
C17 C21 1.416(7) . ?
C18 C34 1.547(6) . ?
C19 C29 1.377(7) . ?
C19 C23 1.390(6) . ?
C20 C23 1.388(7) . ?
C21 C29 1.361(7) . ?
C22 C31 1.372(7) . ?
C22 C32 1.381(7) . ?
C25 C27 1.384(7) . ?
C25 C31 1.389(7) . ?
C27 C30 1.412(7) . ?
C28 C33 1.548(6) . ?
C30 C32 1.372(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N1 C24 124.4(6) . . ?
C15 N7 C26 126.4(6) . . ?
C16 N9 C14 123.7(6) . . ?
C14 N10 C13 126.6(5) . . ?
C16 C11 C18 109.6(5) . . ?
C16 C11 C13 113.6(5) . . ?
C18 C11 C13 106.9(4) . . ?
C16 C11 C27 105.7(5) . . ?
C18 C11 C27 113.7(5) . . ?
C13 C11 C27 107.3(5) . . ?
C24 C12 C28 110.4(5) . . ?
C24 C12 C26 113.1(5) . . ?
C28 C12 C26 109.2(5) . . ?
C24 C12 C20 110.0(5) . . ?
C28 C12 C20 109.0(4) . . ?
C26 C12 C20 104.8(5) . . ?
O7 C13 N10 119.8(6) . . ?
O7 C13 C11 123.6(6) . . ?
N10 C13 C11 116.6(6) . . ?
O1 C14 N10 121.7(6) . . ?
O1 C14 N9 121.0(6) . . ?
N10 C14 N9 117.2(6) . . ?
O5 C15 N7 123.7(6) . . ?
O5 C15 N1 119.1(6) . . ?
N7 C15 N1 117.1(6) . . ?
O2 C16 N9 118.4(6) . . ?
O2 C16 C11 121.4(6) . . ?
N9 C16 C11 120.2(6) . . ?
C20 C17 C21 117.3(6) . . ?
C11 C18 C34 112.2(5) . . ?
C29 C19 C23 118.4(6) . . ?
C23 C20 C17 121.0(6) . . ?
C23 C20 C12 119.6(6) . . ?
C17 C20 C12 119.4(6) . . ?
C29 C21 C17 120.3(6) . . ?
C31 C22 C32 120.4(6) . . ?
C20 C23 C19 120.4(6) . . ?
O3 C24 N1 118.4(6) . . ?
O3 C24 C12 125.3(6) . . ?
N1 C24 C12 116.0(6) . . ?
C27 C25 C31 120.7(5) . . ?
O4 C26 N7 119.2(6) . . ?
O4 C26 C12 126.4(6) . . ?
N7 C26 C12 114.2(6) . . ?
C25 C27 C30 118.6(5) . . ?
C25 C27 C11 122.5(5) . . ?
C30 C27 C11 118.8(5) . . ?
C12 C28 C33 112.9(4) . . ?
C21 C29 C19 122.4(6) . . ?
C32 C30 C27 120.1(6) . . ?
C22 C31 C25 119.9(6) . . ?
C30 C32 C22 120.4(6) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        54.24
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.143
_exptl_crystal_recrystallization_method 'From the Melt'
