# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_efonidipine
_database_code_depnum_ccdc_archive 'CCDC 1060363'
_audit_update_record             
;
2015-07-31 deposited with the CCDC.
2015-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 efonidipine 
;
_chemical_name_common            'NZ-105 free form'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H38 N3 O7 P'
_chemical_formula_weight         631.64

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.9296(5)
_cell_length_b                   13.1794(7)
_cell_length_c                   24.2673(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3175.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      65.67

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    1.210
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8393
_exptl_absorpt_correction_T_max  0.8886
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'TURBO X-RAY SOURCE'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            46156
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         65.67
_reflns_number_total             5382
_reflns_number_gt                4222
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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+0.8891P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    const
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_number_reflns         5382
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_restrained_S_all      0.858
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7649(3) 0.3065(2) 0.83463(13) 0.0374(7) Uani 1 1 d . . .
C2 C 0.6776(3) 0.3546(2) 0.79887(13) 0.0427(7) Uani 1 1 d . . .
H2 H 0.6841 0.4242 0.7933 0.051 Uiso 1 1 calc R . .
C3 C 0.5805(3) 0.2991(3) 0.77133(13) 0.0438(8) Uani 1 1 d . . .
C4 C 0.5662(3) 0.1954(2) 0.77815(14) 0.0452(8) Uani 1 1 d . . .
H4 H 0.5006 0.1593 0.7591 0.054 Uiso 1 1 calc R . .
C5 C 0.6522(4) 0.1478(3) 0.81408(14) 0.0496(9) Uani 1 1 d . . .
H5 H 0.6440 0.0784 0.8198 0.060 Uiso 1 1 calc R . .
C6 C 0.7514(4) 0.2016(2) 0.84200(14) 0.0462(8) Uani 1 1 d . . .
H6 H 0.8093 0.1677 0.8658 0.055 Uiso 1 1 calc R . .
C7 C 0.8755(3) 0.3655(2) 0.86443(12) 0.0382(7) Uani 1 1 d . . .
H7 H 0.8936 0.3313 0.8995 0.046 Uiso 1 1 calc R . .
C8 C 0.8310(3) 0.4727(2) 0.87689(12) 0.0361(7) Uani 1 1 d . . .
C9 C 0.8596(3) 0.5498(2) 0.84118(12) 0.0396(7) Uani 1 1 d . . .
C10 C 1.0293(3) 0.4462(2) 0.79656(12) 0.0385(7) Uani 1 1 d . . .
C11 C 1.0067(3) 0.3662(2) 0.83074(12) 0.0367(7) Uani 1 1 d . . .
C12 C 0.8106(4) 0.6569(2) 0.84256(15) 0.0561(9) Uani 1 1 d . . .
H12A H 0.7140 0.6574 0.8435 0.084 Uiso 1 1 calc R . .
H12B H 0.8413 0.6920 0.8102 0.084 Uiso 1 1 calc R . .
H12C H 0.8451 0.6901 0.8748 0.084 Uiso 1 1 calc R . .
C13 C 1.1435(3) 0.4568(3) 0.75607(13) 0.0467(8) Uani 1 1 d . . .
H13A H 1.2210 0.4839 0.7746 0.070 Uiso 1 1 calc R . .
H13B H 1.1171 0.5018 0.7269 0.070 Uiso 1 1 calc R . .
H13C H 1.1650 0.3915 0.7410 0.070 Uiso 1 1 calc R . .
C14 C 1.1583(3) 0.2563(3) 0.93713(12) 0.0429(7) Uani 1 1 d . . .
H14A H 1.1496 0.2120 0.9688 0.052 Uiso 1 1 calc R . .
H14B H 1.1113 0.3190 0.9454 0.052 Uiso 1 1 calc R . .
C15 C 1.3070(3) 0.2795(2) 0.92781(13) 0.0427(7) Uani 1 1 d . . .
C16 C 1.3175(4) 0.3451(2) 0.87554(13) 0.0466(8) Uani 1 1 d . . .
H16A H 1.2698 0.4084 0.8813 0.056 Uiso 1 1 calc R . .
H16B H 1.4114 0.3610 0.8685 0.056 Uiso 1 1 calc R . .
C17 C 1.3882(4) 0.1824(2) 0.92032(15) 0.0521(8) Uani 1 1 d . . .
H17A H 1.3800 0.1411 0.9527 0.078 Uiso 1 1 calc R . .
H17B H 1.4812 0.1992 0.9145 0.078 Uiso 1 1 calc R . .
H17C H 1.3547 0.1457 0.8890 0.078 Uiso 1 1 calc R . .
C18 C 1.3596(4) 0.3389(3) 0.97709(15) 0.0584(10) Uani 1 1 d . . .
H18A H 1.3075 0.3997 0.9816 0.088 Uiso 1 1 calc R . .
H18B H 1.4523 0.3565 0.9711 0.088 Uiso 1 1 calc R . .
H18C H 1.3523 0.2980 1.0097 0.088 Uiso 1 1 calc R . .
C19 C 0.7505(3) 0.4832(2) 0.92674(13) 0.0406(7) Uani 1 1 d . . .
C20 C 0.6283(4) 0.5983(3) 0.98422(14) 0.0555(9) Uani 1 1 d . . .
H20A H 0.6978 0.6166 1.0105 0.067 Uiso 1 1 calc R . .
H20B H 0.5783 0.5410 0.9989 0.067 Uiso 1 1 calc R . .
C21 C 0.5355(4) 0.6865(3) 0.97453(16) 0.0545(9) Uani 1 1 d . . .
H21A H 0.5221 0.7219 1.0091 0.065 Uiso 1 1 calc R . .
H21B H 0.5785 0.7333 0.9492 0.065 Uiso 1 1 calc R . .
C22 C 0.3070(4) 0.6188(2) 0.98691(15) 0.0483(8) Uani 1 1 d . . .
C23 C 0.1830(4) 0.5865(3) 0.96652(15) 0.0554(9) Uani 1 1 d . . .
H23 H 0.1637 0.5935 0.9292 0.066 Uiso 1 1 calc R . .
C24 C 0.0886(4) 0.5442(3) 1.00142(18) 0.0616(10) Uani 1 1 d . . .
H24 H 0.0065 0.5227 0.9870 0.074 Uiso 1 1 calc R . .
C25 C 0.1127(4) 0.5330(3) 1.05690(18) 0.0627(10) Uani 1 1 d . . .
H25 H 0.0493 0.5029 1.0799 0.075 Uiso 1 1 calc R . .
C26 C 0.2335(4) 0.5675(3) 1.07744(16) 0.0586(10) Uani 1 1 d . . .
H26 H 0.2502 0.5627 1.1151 0.070 Uiso 1 1 calc R . .
C27 C 0.3294(4) 0.6088(3) 1.04378(14) 0.0519(9) Uani 1 1 d . . .
H27 H 0.4106 0.6304 1.0588 0.062 Uiso 1 1 calc R . .
C28 C 0.3852(4) 0.6611(3) 0.89300(15) 0.0629(10) Uani 1 1 d . . .
H28A H 0.3460 0.5971 0.8815 0.075 Uiso 1 1 calc R . .
H28B H 0.4721 0.6674 0.8750 0.075 Uiso 1 1 calc R . .
C29 C 0.2953(4) 0.7465(3) 0.87355(13) 0.0533(9) Uani 1 1 d . . .
C30 C 0.3115(4) 0.8433(3) 0.89320(16) 0.0656(11) Uani 1 1 d . . .
H30 H 0.3762 0.8558 0.9201 0.079 Uiso 1 1 calc R . .
C31 C 0.2341(5) 0.9222(3) 0.87402(18) 0.0789(13) Uani 1 1 d . . .
H31 H 0.2481 0.9874 0.8875 0.095 Uiso 1 1 calc R . .
C32 C 0.1383(5) 0.9057(4) 0.83585(18) 0.0749(12) Uani 1 1 d . . .
H32 H 0.0854 0.9592 0.8234 0.090 Uiso 1 1 calc R . .
C33 C 0.1188(5) 0.8103(4) 0.81551(17) 0.0788(13) Uani 1 1 d . . .
H33 H 0.0530 0.7985 0.7890 0.095 Uiso 1 1 calc R . .
C34 C 0.1977(5) 0.7313(3) 0.83464(15) 0.0703(12) Uani 1 1 d . . .
H34 H 0.1841 0.6664 0.8207 0.084 Uiso 1 1 calc R . .
N1 N 0.4901(3) 0.3522(2) 0.73349(12) 0.0524(7) Uani 1 1 d . . .
N2 N 0.9461(3) 0.53069(18) 0.79810(10) 0.0403(6) Uani 1 1 d . . .
H2A H 0.9487 0.5728 0.7710 0.048 Uiso 1 1 calc R . .
N3 N 0.4063(3) 0.6584(2) 0.95259(12) 0.0592(8) Uani 1 1 d . . .
O1 O 0.4201(3) 0.3032(2) 0.70240(11) 0.0646(7) Uani 1 1 d . . .
O2 O 0.4867(3) 0.4446(2) 0.73582(14) 0.0814(9) Uani 1 1 d . . .
O3 O 1.0802(2) 0.18351(17) 0.78771(9) 0.0527(6) Uani 1 1 d . . .
O4 O 1.2616(2) 0.29358(15) 0.82819(8) 0.0423(5) Uani 1 1 d . . .
O5 O 1.0949(2) 0.20823(15) 0.88978(8) 0.0408(5) Uani 1 1 d . . .
O6 O 0.7397(3) 0.41799(19) 0.96151(10) 0.0659(7) Uani 1 1 d . . .
O7 O 0.6879(3) 0.57210(18) 0.93172(9) 0.0570(6) Uani 1 1 d . . .
P1 P 1.10970(8) 0.25740(6) 0.83125(3) 0.0386(2) 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 1.381(4) . ?
C1 C6 1.400(4) . ?
C1 C7 1.527(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 N1 1.463(4) . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.512(4) . ?
C7 C11 1.538(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.365(4) . ?
C8 C19 1.457(4) . ?
C9 N2 1.376(4) . ?
C9 C12 1.493(4) . ?
C10 C11 1.360(4) . ?
C10 N2 1.387(4) . ?
C10 C13 1.506(4) . ?
C11 P1 1.762(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O5 1.456(4) . ?
C14 C15 1.524(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C18 1.522(4) . ?
C15 C17 1.524(4) . ?
C15 C16 1.538(4) . ?
C16 O4 1.445(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O6 1.209(4) . ?
C19 O7 1.331(4) . ?
C20 O7 1.447(4) . ?
C20 C21 1.502(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 N3 1.438(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N3 1.392(4) . ?
C22 C23 1.394(5) . ?
C22 C27 1.404(5) . ?
C23 C24 1.381(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.376(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.367(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 N3 1.461(5) . ?
C28 C29 1.513(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C34 1.368(5) . ?
C29 C30 1.371(5) . ?
C30 C31 1.374(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.346(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.364(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.383(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N1 O1 1.212(4) . ?
N1 O2 1.219(4) . ?
N2 H2A 0.8600 . ?
O3 P1 1.466(2) . ?
O4 P1 1.584(2) . ?
O5 P1 1.568(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
C2 C1 C6 118.2(3) . . ?
C2 C1 C7 121.0(3) . . ?
C6 C1 C7 120.7(3) . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 122.4(3) . . ?
C2 C3 N1 118.6(3) . . ?
C4 C3 N1 119.0(3) . . ?
C5 C4 C3 117.6(3) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 C1 111.2(3) . . ?
C8 C7 C11 110.3(2) . . ?
C1 C7 C11 111.1(2) . . ?
C8 C7 H7 108.0 . . ?
C1 C7 H7 108.0 . . ?
C11 C7 H7 108.0 . . ?
C9 C8 C19 124.8(3) . . ?
C9 C8 C7 120.5(3) . . ?
C19 C8 C7 114.5(3) . . ?
C8 C9 N2 118.4(3) . . ?
C8 C9 C12 128.4(3) . . ?
N2 C9 C12 113.2(3) . . ?
C11 C10 N2 120.5(3) . . ?
C11 C10 C13 126.5(3) . . ?
N2 C10 C13 113.0(3) . . ?
C10 C11 C7 118.0(3) . . ?
C10 C11 P1 122.6(2) . . ?
C7 C11 P1 118.9(2) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 C15 112.9(2) . . ?
O5 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
O5 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C18 C15 C17 110.1(3) . . ?
C18 C15 C14 108.6(3) . . ?
C17 C15 C14 111.2(3) . . ?
C18 C15 C16 109.6(3) . . ?
C17 C15 C16 109.7(3) . . ?
C14 C15 C16 107.5(2) . . ?
O4 C16 C15 111.4(2) . . ?
O4 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
O4 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 C19 O7 121.4(3) . . ?
O6 C19 C8 124.1(3) . . ?
O7 C19 C8 114.5(3) . . ?
O7 C20 C21 107.3(3) . . ?
O7 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O7 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?
N3 C21 C20 114.0(3) . . ?
N3 C21 H21A 108.8 . . ?
C20 C21 H21A 108.8 . . ?
N3 C21 H21B 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
N3 C22 C23 121.9(3) . . ?
N3 C22 C27 120.7(3) . . ?
C23 C22 C27 117.4(3) . . ?
C24 C23 C22 120.4(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 121.7(4) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 118.1(4) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C27 C26 C25 121.5(4) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C22 120.9(4) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
N3 C28 C29 114.3(3) . . ?
N3 C28 H28A 108.7 . . ?
C29 C28 H28A 108.7 . . ?
N3 C28 H28B 108.7 . . ?
C29 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C34 C29 C30 117.3(4) . . ?
C34 C29 C28 121.7(4) . . ?
C30 C29 C28 121.0(3) . . ?
C29 C30 C31 121.4(4) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C32 C31 C30 120.4(4) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C33 119.9(4) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C32 C33 C34 119.5(4) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C29 C34 C33 121.5(4) . . ?
C29 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
O1 N1 O2 123.0(3) . . ?
O1 N1 C3 119.2(3) . . ?
O2 N1 C3 117.8(3) . . ?
C9 N2 C10 122.6(2) . . ?
C9 N2 H2A 118.7 . . ?
C10 N2 H2A 118.7 . . ?
C22 N3 C21 120.5(3) . . ?
C22 N3 C28 120.0(3) . . ?
C21 N3 C28 119.2(3) . . ?
C16 O4 P1 118.0(2) . . ?
C14 O5 P1 119.63(18) . . ?
C19 O7 C20 118.7(3) . . ?
O3 P1 O5 111.07(13) . . ?
O3 P1 O4 110.86(13) . . ?
O5 P1 O4 104.85(12) . . ?
O3 P1 C11 114.81(14) . . ?
O5 P1 C11 106.75(13) . . ?
O4 P1 C11 107.93(13) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        65.67
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_efonidipine_hydrochloride_ethanolate
_database_code_depnum_ccdc_archive 'CCDC 1060364'
_audit_update_record             
;
2015-07-31 deposited with the CCDC.
2015-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 efonidipine hydrochloride ethanolate
;
_chemical_name_common            NZ-105
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H45 Cl N3 O8 P'
_chemical_formula_weight         714.17

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4763(11)
_cell_length_b                   11.9281(12)
_cell_length_c                   15.1054(15)
_cell_angle_alpha                87.156(5)
_cell_angle_beta                 78.155(5)
_cell_angle_gamma                64.918(4)
_cell_volume                     1831.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296
_cell_measurement_reflns_used    9998
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      64.75

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             756
_exptl_absorpt_coefficient_mu    1.784
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7757
_exptl_absorpt_correction_T_max  0.8704
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'TURBO X-RAY SOURCE'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            25692
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         65.63
_reflns_number_total             5958
_reflns_number_gt                5362
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. we used SHELXL restraints 
 and constraints commands of the following lines. 
 comands at the refinement.  
 sadi 0.01 C2EA O1EA C2EB O1EB
 sadi 0.01 C2EA C1EA C2EB C1EB
 EADP O1EA O1EB
 EADP C2EA C2EB
 EADP C1EA C1EB
 DFIX 1.43 0.01 O1EA C2EA  O1EB C2EB
 DFIX 1.54 0.01 C1EA C2EA  C1EB C2EB
 ISOR 0.02 C2EA C1EA C2EB C1EB O1EA O1EB 
;

_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+0.6811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    const
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5958
_refine_ls_number_parameters     455
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.091
_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
C1 C 0.46966(18) 0.25064(18) 0.89974(13) 0.0283(4) Uani 1 1 d . A 4
C2 C 0.57785(19) 0.25631(19) 0.84199(14) 0.0325(4) Uani 1 1 d . A 4
H2 H 0.5671 0.3113 0.7952 0.039 Uiso 1 1 calc R A 4
C3 C 0.7018(2) 0.1784(2) 0.85556(15) 0.0368(5) Uani 1 1 d . A 4
C4 C 0.7229(2) 0.0949(2) 0.92286(16) 0.0413(5) Uani 1 1 d . A 4
H4 H 0.8077 0.0434 0.9300 0.050 Uiso 1 1 calc R A 4
C5 C 0.6147(2) 0.0893(2) 0.97994(15) 0.0381(5) Uani 1 1 d . A 4
H5 H 0.6264 0.0331 1.0259 0.046 Uiso 1 1 calc R A 4
C6 C 0.4895(2) 0.16686(19) 0.96882(14) 0.0325(4) Uani 1 1 d . A 4
H6 H 0.4174 0.1631 1.0080 0.039 Uiso 1 1 calc R A 4
C7 C 0.33001(18) 0.33543(18) 0.88879(13) 0.0280(4) Uani 1 1 d . A 4
H7 H 0.3355 0.3811 0.8335 0.034 Uiso 1 1 calc R A 4
C8 C 0.25842(18) 0.42899(18) 0.96880(13) 0.0295(4) Uani 1 1 d . A 4
C9 C 0.16566(19) 0.41624(18) 1.03478(13) 0.0320(4) Uani 1 1 d . A 4
C10 C 0.16070(19) 0.25386(18) 0.94736(13) 0.0307(4) Uani 1 1 d . A 4
C11 C 0.25474(18) 0.25850(18) 0.87894(13) 0.0301(4) Uani 1 1 d . A 4
C12 C 0.1013(2) 0.4914(2) 1.12218(15) 0.0420(5) Uani 1 1 d . A 4
H12A H 0.1132 0.5666 1.1172 0.063 Uiso 1 1 calc R A 4
H12B H 0.1405 0.4446 1.1702 0.063 Uiso 1 1 calc R A 4
H12C H 0.0092 0.5110 1.1350 0.063 Uiso 1 1 calc R A 4
C13 C 0.0856(2) 0.1764(2) 0.94962(15) 0.0385(5) Uani 1 1 d . A 4
H13A H 0.0029 0.2252 0.9326 0.058 Uiso 1 1 calc R A 4
H13B H 0.0702 0.1482 1.0097 0.058 Uiso 1 1 calc R A 4
H13C H 0.1356 0.1062 0.9080 0.058 Uiso 1 1 calc R A 4
C14 C 0.2791(2) 0.3322(2) 0.66634(15) 0.0429(5) Uani 1 1 d . A 4
H14A H 0.3254 0.3633 0.6177 0.052 Uiso 1 1 calc R A 4
H14B H 0.2302 0.3978 0.7128 0.052 Uiso 1 1 calc R A 4
C15 C 0.1838(2) 0.2982(2) 0.63018(14) 0.0400(5) Uani 1 1 d . A 4
C16 C 0.1131(2) 0.2475(2) 0.70696(15) 0.0401(5) Uani 1 1 d . A 4
H16A H 0.0600 0.3126 0.7533 0.048 Uiso 1 1 calc R A 4
H16B H 0.0549 0.2219 0.6839 0.048 Uiso 1 1 calc R A 4
C17 C 0.2565(3) 0.2022(3) 0.55152(16) 0.0527(6) Uani 1 1 d . A 4
H17A H 0.3232 0.1303 0.5713 0.079 Uiso 1 1 calc R A 4
H17B H 0.2966 0.2369 0.5026 0.079 Uiso 1 1 calc R A 4
H17C H 0.1955 0.1790 0.5313 0.079 Uiso 1 1 calc R A 4
C18 C 0.0815(3) 0.4159(3) 0.5999(2) 0.0671(8) Uani 1 1 d . A 4
H18A H 0.0196 0.3964 0.5774 0.101 Uiso 1 1 calc R A 4
H18B H 0.1241 0.4510 0.5530 0.101 Uiso 1 1 calc R A 4
H18C H 0.0362 0.4744 0.6504 0.101 Uiso 1 1 calc R A 4
C19 C 0.2965(2) 0.53080(19) 0.97416(14) 0.0333(4) Uani 1 1 d . A 4
C20 C 0.4461(2) 0.6129(2) 0.90130(15) 0.0394(5) Uani 1 1 d . A 4
H20A H 0.5355 0.5783 0.8665 0.047 Uiso 1 1 calc R A 4
H20B H 0.4491 0.6286 0.9630 0.047 Uiso 1 1 calc R A 4
C21 C 0.3683(2) 0.7332(2) 0.86246(15) 0.0418(5) Uani 1 1 d . A 4
H21A H 0.4131 0.7866 0.8609 0.050 Uiso 1 1 calc R A 4
H21B H 0.2832 0.7733 0.9026 0.050 Uiso 1 1 calc R A 4
C22 C 0.4636(2) 0.6353(2) 0.70613(14) 0.0365(5) Uani 1 1 d . A 4
C23 C 0.5809(2) 0.6462(3) 0.69279(18) 0.0504(6) Uani 1 1 d . A 4
H23 H 0.5875 0.7089 0.7228 0.060 Uiso 1 1 calc R A 4
C24 C 0.6885(3) 0.5620(3) 0.6338(2) 0.0623(8) Uani 1 1 d . A 4
H24 H 0.7685 0.5676 0.6246 0.075 Uiso 1 1 calc R A 4
C25 C 0.6786(3) 0.4706(3) 0.5886(2) 0.0671(8) Uani 1 1 d . A 4
H25 H 0.7517 0.4144 0.5492 0.081 Uiso 1 1 calc R A 4
C26 C 0.5609(3) 0.4619(3) 0.6016(2) 0.0635(7) Uani 1 1 d . A 4
H26 H 0.5542 0.4003 0.5704 0.076 Uiso 1 1 calc R A 4
C27 C 0.4522(2) 0.5442(2) 0.66083(17) 0.0456(5) Uani 1 1 d . A 4
H27 H 0.3724 0.5381 0.6699 0.055 Uiso 1 1 calc R A 4
C28 C 0.2894(3) 0.8514(2) 0.73236(16) 0.0453(5) Uani 1 1 d . A 4
H28A H 0.2058 0.9001 0.7718 0.054 Uiso 1 1 calc R A 4
H28B H 0.3478 0.8904 0.7346 0.054 Uiso 1 1 calc R A 4
C29 C 0.2684(2) 0.8534(2) 0.63672(16) 0.0445(5) Uani 1 1 d . A 4
C30 C 0.1555(3) 0.8526(3) 0.6203(2) 0.0612(7) Uani 1 1 d . A 4
H30 H 0.0923 0.8484 0.6682 0.073 Uiso 1 1 calc R A 4
C31 C 0.1354(4) 0.8579(3) 0.5330(2) 0.0777(9) Uani 1 1 d . A 4
H31 H 0.0594 0.8560 0.5221 0.093 Uiso 1 1 calc R A 4
C32 C 0.2273(4) 0.8659(3) 0.4624(2) 0.0785(10) Uani 1 1 d . A 4
H32 H 0.2129 0.8704 0.4036 0.094 Uiso 1 1 calc R A 4
C33 C 0.3405(4) 0.8674(3) 0.4777(2) 0.0722(9) Uani 1 1 d . A 4
H33 H 0.4031 0.8722 0.4295 0.087 Uiso 1 1 calc R A 4
C34 C 0.3609(3) 0.8616(2) 0.56578(19) 0.0561(7) Uani 1 1 d . A 4
H34 H 0.4370 0.8632 0.5767 0.067 Uiso 1 1 calc R A 4
Cl1 Cl 0.11385(5) 0.66034(6) 0.80659(4) 0.0517(2) Uani 1 1 d . B 4
N1 N 0.81633(19) 0.1854(2) 0.79482(15) 0.0524(5) Uani 1 1 d . A 4
N2 N 0.12300(16) 0.32713(16) 1.02516(11) 0.0346(4) Uani 1 1 d . A 4
H2A H 0.0697 0.3162 1.0701 0.041 Uiso 1 1 calc R A 4
N3 N 0.34731(17) 0.72161(16) 0.76827(12) 0.0353(4) Uani 1 1 d . A 4
H3 H 0.2850 0.6921 0.7741 0.042 Uiso 1 1 calc R A 4
O1 O 0.92555(17) 0.1101(2) 0.80322(17) 0.0774(7) Uani 1 1 d . A 4
O2 O 0.79783(19) 0.2665(3) 0.73992(15) 0.0838(8) Uani 1 1 d . A 4
O3 O 0.41929(16) 0.03351(15) 0.79284(12) 0.0522(4) Uani 1 1 d . A 4
O4 O 0.20502(14) 0.14332(13) 0.74662(10) 0.0358(3) Uani 1 1 d . A 4
O5 O 0.37386(14) 0.22714(15) 0.70404(10) 0.0388(4) Uani 1 1 d . A 4
O6 O 0.25508(17) 0.61222(15) 1.03241(11) 0.0479(4) Uani 1 1 d . A 4
O7 O 0.39254(14) 0.52382(13) 0.90130(9) 0.0341(3) Uani 1 1 d . A 4
P1 P 0.31888(5) 0.15717(5) 0.78118(3) 0.03255(17) Uani 1 1 d . A 4
C1EA C 0.8161(12) 0.8056(12) 0.6810(6) 0.114(3) Uani 0.50 1 d PDU C 1
H1E1 H 0.8845 0.7249 0.6853 0.170 Uiso 0.50 1 calc PR C 1
H1E2 H 0.8530 0.8562 0.6456 0.170 Uiso 0.50 1 calc PR C 1
H1E3 H 0.7522 0.7980 0.6525 0.170 Uiso 0.50 1 calc PR C 1
C2EA C 0.751(2) 0.8648(10) 0.7745(8) 0.071(2) Uani 0.50 1 d PDU C 1
H2E1 H 0.8142 0.8384 0.8137 0.085 Uiso 0.50 1 calc PR C 1
H2E2 H 0.7148 0.9543 0.7720 0.085 Uiso 0.50 1 calc PR C 1
O1EA O 0.650(3) 0.827(3) 0.808(4) 0.083(3) Uani 0.50 1 d PDU C 1
C1EB C 0.7602(12) 0.9040(12) 0.6984(6) 0.114(3) Uani 0.50 1 d PDU D 2
H1E4 H 0.6968 0.9039 0.6658 0.170 Uiso 0.50 1 calc PR D 2
H1E5 H 0.8454 0.8730 0.6592 0.170 Uiso 0.50 1 calc PR D 2
H1E6 H 0.7363 0.9870 0.7195 0.170 Uiso 0.50 1 calc PR D 2
C2EB C 0.764(2) 0.8228(10) 0.7779(8) 0.071(2) Uani 0.50 1 d PDU D 2
H2E3 H 0.8147 0.7364 0.7581 0.085 Uiso 0.50 1 calc PR D 2
H2E4 H 0.8040 0.8425 0.8217 0.085 Uiso 0.50 1 calc PR D 2
O1EB O 0.634(3) 0.844(3) 0.817(4) 0.083(3) Uani 0.50 1 d PDU D 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 C2 1.389(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.529(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 N1 1.471(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.526(3) . ?
C7 C11 1.533(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.355(3) . ?
C8 C19 1.465(3) . ?
C9 N2 1.370(3) . ?
C9 C12 1.499(3) . ?
C10 C11 1.350(3) . ?
C10 N2 1.380(3) . ?
C10 C13 1.503(3) . ?
C11 P1 1.778(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O5 1.451(3) . ?
C14 C15 1.518(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C18 1.522(3) . ?
C15 C16 1.525(3) . ?
C15 C17 1.529(3) . ?
C16 O4 1.446(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O6 1.210(3) . ?
C19 O7 1.366(2) . ?
C20 O7 1.435(2) . ?
C20 C21 1.498(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 N3 1.513(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C27 1.378(3) . ?
C22 C23 1.380(3) . ?
C22 N3 1.462(3) . ?
C23 C24 1.384(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.382(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.510(3) . ?
C28 N3 1.525(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.373(4) . ?
C29 C34 1.376(4) . ?
C30 C31 1.378(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.369(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.373(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.391(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N1 O2 1.220(3) . ?
N1 O1 1.222(3) . ?
N2 H2A 0.8600 . ?
N3 H3 0.9100 . ?
O3 P1 1.4667(17) . ?
O4 P1 1.5744(14) . ?
O5 P1 1.5814(16) . ?
C1EA C2EA 1.506(7) . ?
C1EA H1E1 0.9600 . ?
C1EA H1E2 0.9600 . ?
C1EA H1E3 0.9600 . ?
C2EA O1EA 1.409(8) . ?
C2EA H2E1 0.9700 . ?
C2EA H2E2 0.9700 . ?
C1EB C2EB 1.501(7) . ?
C1EB H1E4 0.9600 . ?
C1EB H1E5 0.9600 . ?
C1EB H1E6 0.9600 . ?
C2EB O1EB 1.407(8) . ?
C2EB H2E3 0.9700 . ?
C2EB H2E4 0.9700 . ?

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 119.17(18) . . ?
C2 C1 C7 120.91(18) . . ?
C6 C1 C7 119.92(17) . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 123.0(2) . . ?
C4 C3 N1 118.58(19) . . ?
C2 C3 N1 118.4(2) . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.93(19) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C1 110.49(15) . . ?
C8 C7 C11 110.93(16) . . ?
C1 C7 C11 110.28(16) . . ?
C8 C7 H7 108.3 . . ?
C1 C7 H7 108.3 . . ?
C11 C7 H7 108.3 . . ?
C9 C8 C19 120.71(18) . . ?
C9 C8 C7 121.24(18) . . ?
C19 C8 C7 118.01(17) . . ?
C8 C9 N2 120.04(18) . . ?
C8 C9 C12 126.3(2) . . ?
N2 C9 C12 113.62(18) . . ?
C11 C10 N2 120.05(18) . . ?
C11 C10 C13 127.02(19) . . ?
N2 C10 C13 112.92(17) . . ?
C10 C11 C7 121.21(18) . . ?
C10 C11 P1 122.59(16) . . ?
C7 C11 P1 115.31(14) . . ?
O5 C14 C15 112.02(18) . . ?
O5 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
O5 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C18 108.2(2) . . ?
C14 C15 C16 108.68(18) . . ?
C18 C15 C16 108.0(2) . . ?
C14 C15 C17 110.59(19) . . ?
C18 C15 C17 110.8(2) . . ?
C16 C15 C17 110.5(2) . . ?
O4 C16 C15 111.54(17) . . ?
O4 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
O4 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
O6 C19 O7 121.03(19) . . ?
O6 C19 C8 128.60(19) . . ?
O7 C19 C8 110.36(17) . . ?
O7 C20 C21 113.10(17) . . ?
O7 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
O7 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 N3 114.74(18) . . ?
C20 C21 H21A 108.6 . . ?
N3 C21 H21A 108.6 . . ?
C20 C21 H21B 108.6 . . ?
N3 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C27 C22 C23 121.2(2) . . ?
C27 C22 N3 118.20(19) . . ?
C23 C22 N3 120.6(2) . . ?
C22 C23 C24 118.6(3) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 119.1(2) . . ?
C22 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
C29 C28 N3 113.80(18) . . ?
C29 C28 H28A 108.8 . . ?
N3 C28 H28A 108.8 . . ?
C29 C28 H28B 108.8 . . ?
N3 C28 H28B 108.8 . . ?
H28A C28 H28B 107.7 . . ?
C30 C29 C34 119.7(3) . . ?
C30 C29 C28 120.6(2) . . ?
C34 C29 C28 119.6(2) . . ?
C29 C30 C31 120.3(3) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C32 C31 C30 120.0(3) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C33 120.4(3) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C34 119.5(3) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C29 C34 C33 120.0(3) . . ?
C29 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
O2 N1 O1 123.4(2) . . ?
O2 N1 C3 118.7(2) . . ?
O1 N1 C3 117.8(2) . . ?
C9 N2 C10 123.66(17) . . ?
C9 N2 H2A 118.2 . . ?
C10 N2 H2A 118.2 . . ?
C22 N3 C21 114.53(17) . . ?
C22 N3 C28 112.97(17) . . ?
C21 N3 C28 108.02(16) . . ?
C22 N3 H3 107.0 . . ?
C21 N3 H3 107.0 . . ?
C28 N3 H3 107.0 . . ?
C16 O4 P1 119.39(13) . . ?
C14 O5 P1 117.62(13) . . ?
C19 O7 C20 116.24(16) . . ?
O3 P1 O4 109.00(9) . . ?
O3 P1 O5 111.66(10) . . ?
O4 P1 O5 104.60(8) . . ?
O3 P1 C11 114.84(10) . . ?
O4 P1 C11 110.66(8) . . ?
O5 P1 C11 105.58(9) . . ?
C2EA C1EA H1E1 109.5 . . ?
C2EA C1EA H1E2 109.5 . . ?
H1E1 C1EA H1E2 109.5 . . ?
C2EA C1EA H1E3 109.5 . . ?
H1E1 C1EA H1E3 109.5 . . ?
H1E2 C1EA H1E3 109.5 . . ?
O1EA C2EA C1EA 107(3) . . ?
O1EA C2EA H2E1 110.3 . . ?
C1EA C2EA H2E1 110.3 . . ?
O1EA C2EA H2E2 110.3 . . ?
C1EA C2EA H2E2 110.3 . . ?
H2E1 C2EA H2E2 108.5 . . ?
C2EB C1EB H1E4 109.5 . . ?
C2EB C1EB H1E5 109.5 . . ?
H1E4 C1EB H1E5 109.5 . . ?
C2EB C1EB H1E6 109.5 . . ?
H1E4 C1EB H1E6 109.5 . . ?
H1E5 C1EB H1E6 109.5 . . ?
O1EB C2EB C1EB 108(3) . . ?
O1EB C2EB H2E3 110.1 . . ?
C1EB C2EB H2E3 110.1 . . ?
O1EB C2EB H2E4 110.1 . . ?
C1EB C2EB H2E4 110.1 . . ?
H2E3 C2EB H2E4 108.4 . . ?

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        65.63
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.050
