#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/79/2227927.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227927
loop_
_publ_author_name
'Sun, Hongshun'
'Xu, Hong'
'Li, Yu-Long'
_publ_section_title
;
 [2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol
;
_journal_coeditor_code           PV2333
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2987
_journal_paper_doi               10.1107/S1600536810043588
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H16 F N O'
_chemical_formula_moiety         'C19 H16 F N O'
_chemical_formula_sum            'C19 H16 F N O'
_chemical_formula_weight         293.33
_chemical_name_systematic
;
[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.069(2)
_cell_length_b                   24.683(5)
_cell_length_c                   13.275(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     3059.7(13)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5865
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'via ψ scan (North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.178
_refine_ls_extinction_coef       0.0222(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0700P)²+1.00P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1660
_reflns_number_gt                3098
_reflns_number_total             5536
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2333.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227927
_cod_database_fobs_code          2227927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.2535(3) 0.75467(12) 1.27963(19) 0.1195(10) Uani d . 1 . .
O O1 0.1866(2) 0.57598(8) 0.91629(15) 0.0484(5) Uani d . 1 . .
H H1A 0.2535 0.5566 0.9596 0.058 Uiso d R 1 . .
N N1 -0.2147(3) 0.62400(12) 0.6641(2) 0.0629(8) Uani d . 1 . .
C C1 0.1723(5) 0.73584(16) 1.1794(3) 0.0755(11) Uani d . 1 . .
C C2 0.2351(4) 0.72914(15) 1.1055(3) 0.0669(10) Uani d . 1 . .
H H2A 0.3308 0.7382 1.1227 0.080 Uiso calc R 1 . .
C C3 0.1544(3) 0.70875(13) 1.0056(3) 0.0555(8) Uani d . 1 . .
H H3A 0.1963 0.7036 0.9547 0.067 Uiso calc R 1 . .
C C4 0.0109(3) 0.69557(12) 0.9784(2) 0.0481(8) Uani d . 1 . .
C C5 -0.0491(4) 0.70487(14) 1.0557(3) 0.0662(10) Uani d . 1 . .
H H5A -0.1456 0.6974 1.0386 0.079 Uiso calc R 1 . .
C C6 0.0312(5) 0.72479(15) 1.1564(3) 0.0795(12) Uani d . 1 . .
H H6A -0.0094 0.7306 1.2079 0.095 Uiso calc R 1 . .
C C7 -0.0722(3) 0.67043(13) 0.8715(2) 0.0484(8) Uani d . 1 . .
C C8 -0.0453(3) 0.61787(12) 0.8492(2) 0.0458(7) Uani d . 1 . .
C C9 -0.1199(3) 0.59642(13) 0.7432(2) 0.0517(8) Uani d . 1 . .
C C10 -0.2455(3) 0.67573(14) 0.6860(3) 0.0586(9) Uani d . 1 . .
C C11 -0.3457(4) 0.70551(17) 0.6010(3) 0.0779(12) Uani d . 1 . .
H H11A -0.3882 0.6897 0.5328 0.093 Uiso calc R 1 . .
C C12 -0.3812(4) 0.7570(2) 0.6169(4) 0.0897(14) Uani d . 1 . .
H H12A -0.4492 0.7758 0.5603 0.108 Uiso calc R 1 . .
C C13 -0.3157(4) 0.78179(17) 0.7183(4) 0.0858(13) Uani d . 1 . .
H H13A -0.3399 0.8172 0.7283 0.103 Uiso calc R 1 . .
C C14 -0.2163(4) 0.75455(15) 0.8030(3) 0.0696(10) Uani d . 1 . .
H H14A -0.1738 0.7714 0.8702 0.083 Uiso calc R 1 . .
C C15 -0.1780(3) 0.70061(13) 0.7883(3) 0.0544(9) Uani d . 1 . .
C C16 0.0571(3) 0.58239(12) 0.9353(2) 0.0442(7) Uani d . 1 . .
H H16A 0.0780 0.5986 1.0062 0.053 Uiso calc R 1 . .
H H16B 0.0138 0.5472 0.9346 0.053 Uiso calc R 1 . .
C C17 -0.0908(4) 0.54001(14) 0.7175(3) 0.0656(10) Uani d . 1 . .
H H17A -0.0118 0.5217 0.7745 0.079 Uiso calc R 1 . .
C C18 -0.1149(4) 0.52291(16) 0.6044(3) 0.0720(11) Uani d . 1 . .
H H18A -0.1488 0.5501 0.5476 0.086 Uiso calc R 1 . .
H H18B -0.0495 0.4965 0.5945 0.086 Uiso calc R 1 . .
C C19 -0.2152(4) 0.50415(16) 0.6537(3) 0.0748(11) Uani d . 1 . .
H H19A -0.2110 0.4663 0.6745 0.090 Uiso calc R 1 . .
H H19B -0.3103 0.5200 0.6277 0.090 Uiso calc R 1 . .
F F2 -0.9501(3) 0.66225(11) 0.39541(17) 0.1052(8) Uani d . 1 . .
O O2 -0.5786(2) 0.65058(9) 0.94408(17) 0.0597(6) Uani d . 1 . .
H H2B -0.6423 0.6278 0.9302 0.090 Uiso calc R 1 . .
N N2 -0.3504(2) 0.50285(10) 0.93101(18) 0.0451(6) Uani d . 1 . .
C C20 -0.8499(4) 0.63914(14) 0.4840(3) 0.0646(10) Uani d . 1 . .
C C21 -0.8889(4) 0.62502(15) 0.5687(3) 0.0680(10) Uani d . 1 . .
H H21A -0.9808 0.6318 0.5664 0.082 Uiso calc R 1 . .
C C22 -0.7874(3) 0.60039(14) 0.6577(3) 0.0584(9) Uani d . 1 . .
H H22A -0.8115 0.5904 0.7162 0.070 Uiso calc R 1 . .
C C23 -0.6507(3) 0.59032(12) 0.6613(2) 0.0432(7) Uani d . 1 . .
C C24 -0.6163(4) 0.60645(14) 0.5742(3) 0.0620(9) Uani d . 1 . .
H H24A -0.5242 0.6006 0.5760 0.074 Uiso calc R 1 . .
C C25 -0.7164(4) 0.63104(15) 0.4851(3) 0.0719(11) Uani d . 1 . .
H H25A -0.6928 0.6419 0.4268 0.086 Uiso calc R 1 . .
C C26 -0.5441(3) 0.56122(12) 0.7552(2) 0.0415(7) Uani d . 1 . .
C C27 -0.4757(3) 0.58558(11) 0.8541(2) 0.0417(7) Uani d . 1 . .
C C28 -0.3783(3) 0.55476(12) 0.9413(2) 0.0439(7) Uani d . 1 . .
C C29 -0.4175(3) 0.47784(12) 0.8325(2) 0.0419(7) Uani d . 1 . .
C C30 -0.3911(3) 0.42248(12) 0.8223(2) 0.0517(8) Uani d . 1 . .
H H30A -0.3277 0.4038 0.8817 0.062 Uiso calc R 1 . .
C C31 -0.4569(3) 0.39590(14) 0.7268(3) 0.0565(9) Uani d . 1 . .
H H31A -0.4373 0.3594 0.7212 0.068 Uiso calc R 1 . .
C C32 -0.5536(4) 0.42303(14) 0.6370(3) 0.0567(9) Uani d . 1 . .
H H32A -0.5986 0.4046 0.5719 0.068 Uiso calc R 1 . .
C C33 -0.5820(3) 0.47647(13) 0.6448(2) 0.0505(8) Uani d . 1 . .
H H33A -0.6470 0.4942 0.5847 0.061 Uiso calc R 1 . .
C C34 -0.5145(3) 0.50553(12) 0.7426(2) 0.0423(7) Uani d . 1 . .
C C35 -0.5051(3) 0.64418(12) 0.8719(2) 0.0501(8) Uani d . 1 . .
H H35A -0.4149 0.6636 0.9008 0.060 Uiso calc R 1 . .
H H35B -0.5619 0.6603 0.8025 0.060 Uiso calc R 1 . .
C C36 -0.3029(3) 0.58073(13) 1.0480(2) 0.0537(8) Uani d . 1 . .
H H36A -0.3322 0.6181 1.0535 0.064 Uiso calc R 1 . .
C C37 -0.2562(3) 0.54946(14) 1.1518(2) 0.0580(9) Uani d . 1 . .
H H37A -0.2621 0.5673 1.2151 0.070 Uiso calc R 1 . .
H H37B -0.2758 0.5109 1.1474 0.070 Uiso calc R 1 . .
C C38 -0.1478(3) 0.56916(14) 1.1108(2) 0.0567(9) Uani d . 1 . .
H H38A -0.1012 0.5427 1.0812 0.068 Uiso calc R 1 . .
H H38B -0.0874 0.5991 1.1490 0.068 Uiso calc R 1 . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 O1 H1A . . 119.2 ?
C9 N1 C10 . . 117.9(3) ?
F1 C1 C2 . . 118.4(4) ?
F1 C1 C6 . . 118.8(4) ?
C2 C1 C6 . . 122.7(4) ?
C1 C2 C3 . . 118.4(3) ?
C1 C2 H2A . . 120.8 ?
C3 C2 H2A . . 120.8 ?
C2 C3 C4 . . 121.5(3) ?
C2 C3 H3A . . 119.3 ?
C4 C3 H3A . . 119.3 ?
C5 C4 C3 . . 117.7(3) ?
C5 C4 C7 . . 121.9(3) ?
C3 C4 C7 . . 120.3(3) ?
C6 C5 C4 . . 121.3(3) ?
C6 C5 H5A . . 119.4 ?
C4 C5 H5A . . 119.4 ?
C1 C6 C5 . . 118.3(3) ?
C1 C6 H6A . . 120.8 ?
C5 C6 H6A . . 120.8 ?
C8 C7 C15 . . 118.4(3) ?
C8 C7 C4 . . 120.8(3) ?
C15 C7 C4 . . 120.8(3) ?
C7 C8 C9 . . 119.2(3) ?
C7 C8 C16 . . 121.2(3) ?
C9 C8 C16 . . 119.5(3) ?
N1 C9 C8 . . 123.6(3) ?
N1 C9 C17 . . 116.6(3) ?
C8 C9 C17 . . 119.9(3) ?
N1 C10 C11 . . 117.9(4) ?
N1 C10 C15 . . 122.9(3) ?
C11 C10 C15 . . 119.1(4) ?
C12 C11 C10 . . 121.0(4) ?
C12 C11 H11A . . 119.5 ?
C10 C11 H11A . . 119.5 ?
C11 C12 C13 . . 120.1(4) ?
C11 C12 H12A . . 119.9 ?
C13 C12 H12A . . 119.9 ?
C14 C13 C12 . . 120.8(4) ?
C14 C13 H13A . . 119.6 ?
C12 C13 H13A . . 119.6 ?
C13 C14 C15 . . 120.0(4) ?
C13 C14 H14A . . 120.0 ?
C15 C14 H14A . . 120.0 ?
C10 C15 C14 . . 118.8(3) ?
C10 C15 C7 . . 118.0(3) ?
C14 C15 C7 . . 123.2(3) ?
O1 C16 C8 . . 110.1(2) ?
O1 C16 H16A . . 109.7 ?
C8 C16 H16A . . 109.7 ?
O1 C16 H16B . . 109.7 ?
C8 C16 H16B . . 109.7 ?
H16A C16 H16B . . 108.2 ?
C9 C17 C18 . . 121.6(3) ?
C9 C17 C19 . . 119.0(3) ?
C18 C17 C19 . . 58.7(2) ?
C9 C17 H17A . . 115.3 ?
C18 C17 H17A . . 115.3 ?
C19 C17 H17A . . 115.3 ?
C19 C18 C17 . . 61.3(2) ?
C19 C18 H18A . . 117.6 ?
C17 C18 H18A . . 117.6 ?
C19 C18 H18B . . 117.6 ?
C17 C18 H18B . . 117.6 ?
H18A C18 H18B . . 114.7 ?
C18 C19 C17 . . 60.0(2) ?
C18 C19 H19A . . 117.8 ?
C17 C19 H19A . . 117.8 ?
C18 C19 H19B . . 117.8 ?
C17 C19 H19B . . 117.8 ?
H19A C19 H19B . . 114.9 ?
C35 O2 H2B . . 109.5 ?
C28 N2 C29 . . 118.9(2) ?
C25 C20 F2 . . 119.1(3) ?
C25 C20 C21 . . 122.8(3) ?
F2 C20 C21 . . 118.1(3) ?
C20 C21 C22 . . 117.9(3) ?
C20 C21 H21A . . 121.1 ?
C22 C21 H21A . . 121.1 ?
C21 C22 C23 . . 121.2(3) ?
C21 C22 H22A . . 119.4 ?
C23 C22 H22A . . 119.4 ?
C22 C23 C24 . . 118.5(3) ?
C22 C23 C26 . . 120.8(3) ?
C24 C23 C26 . . 120.7(3) ?
C25 C24 C23 . . 120.9(3) ?
C25 C24 H24A . . 119.5 ?
C23 C24 H24A . . 119.5 ?
C20 C25 C24 . . 118.7(3) ?
C20 C25 H25A . . 120.7 ?
C24 C25 H25A . . 120.7 ?
C27 C26 C34 . . 118.7(3) ?
C27 C26 C23 . . 122.4(3) ?
C34 C26 C23 . . 118.9(3) ?
C26 C27 C28 . . 119.3(3) ?
C26 C27 C35 . . 120.7(3) ?
C28 C27 C35 . . 119.9(3) ?
N2 C28 C27 . . 122.6(3) ?
N2 C28 C36 . . 117.6(3) ?
C27 C28 C36 . . 119.8(3) ?
N2 C29 C34 . . 121.9(3) ?
N2 C29 C30 . . 119.0(3) ?
C34 C29 C30 . . 119.1(3) ?
C31 C30 C29 . . 121.0(3) ?
C31 C30 H30A . . 119.5 ?
C29 C30 H30A . . 119.5 ?
C30 C31 C32 . . 120.4(3) ?
C30 C31 H31A . . 119.8 ?
C32 C31 H31A . . 119.8 ?
C33 C32 C31 . . 119.9(3) ?
C33 C32 H32A . . 120.0 ?
C31 C32 H32A . . 120.0 ?
C32 C33 C34 . . 121.2(3) ?
C32 C33 H33A . . 119.4 ?
C34 C33 H33A . . 119.4 ?
C29 C34 C33 . . 118.4(3) ?
C29 C34 C26 . . 118.6(3) ?
C33 C34 C26 . . 123.0(3) ?
O2 C35 C27 . . 113.1(2) ?
O2 C35 H35A . . 109.0 ?
C27 C35 H35A . . 109.0 ?
O2 C35 H35B . . 109.0 ?
C27 C35 H35B . . 109.0 ?
H35A C35 H35B . . 107.8 ?
C28 C36 C37 . . 122.1(3) ?
C28 C36 C38 . . 120.3(3) ?
C37 C36 C38 . . 59.0(2) ?
C28 C36 H36A . . 114.7 ?
C37 C36 H36A . . 114.7 ?
C38 C36 H36A . . 114.7 ?
C38 C37 C36 . . 60.7(2) ?
C38 C37 H37A . . 117.7 ?
C36 C37 H37A . . 117.7 ?
C38 C37 H37B . . 117.7 ?
C36 C37 H37B . . 117.7 ?
H37A C37 H37B . . 114.8 ?
C37 C38 C36 . . 60.4(2) ?
C37 C38 H38A . . 117.7 ?
C36 C38 H38A . . 117.7 ?
C37 C38 H38B . . 117.7 ?
C36 C38 H38B . . 117.7 ?
H38A C38 H38B . . 114.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C1 . 1.357(4) ?
O1 C16 . 1.426(3) ?
O1 H1A . 0.8501 ?
N1 C9 . 1.315(4) ?
N1 C10 . 1.370(4) ?
C1 C2 . 1.361(5) ?
C1 C6 . 1.365(5) ?
C2 C3 . 1.366(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.391(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.390(4) ?
C4 C7 . 1.487(4) ?
C5 C6 . 1.370(5) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 C8 . 1.380(4) ?
C7 C15 . 1.424(4) ?
C8 C9 . 1.425(4) ?
C8 C16 . 1.502(4) ?
C9 C17 . 1.488(4) ?
C10 C11 . 1.407(4) ?
C10 C15 . 1.413(5) ?
C11 C12 . 1.359(6) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.399(6) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.370(5) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.420(5) ?
C14 H14A . 0.9300 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.490(4) ?
C17 C19 . 1.508(5) ?
C17 H17A . 0.9800 ?
C18 C19 . 1.469(5) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
F2 C20 . 1.356(4) ?
O2 C35 . 1.421(3) ?
O2 H2B . 0.8200 ?
N2 C28 . 1.330(4) ?
N2 C29 . 1.373(3) ?
C20 C25 . 1.354(5) ?
C20 C21 . 1.367(5) ?
C21 C22 . 1.381(4) ?
C21 H21A . 0.9300 ?
C22 C23 . 1.381(4) ?
C22 H22A . 0.9300 ?
C23 C24 . 1.384(4) ?
C23 C26 . 1.490(4) ?
C24 C25 . 1.375(4) ?
C24 H24A . 0.9300 ?
C25 H25A . 0.9300 ?
C26 C27 . 1.373(4) ?
C26 C34 . 1.429(4) ?
C27 C28 . 1.425(4) ?
C27 C35 . 1.513(4) ?
C28 C36 . 1.479(4) ?
C29 C34 . 1.405(4) ?
C29 C30 . 1.408(4) ?
C30 C31 . 1.360(4) ?
C30 H30A . 0.9300 ?
C31 C32 . 1.396(4) ?
C31 H31A . 0.9300 ?
C32 C33 . 1.362(4) ?
C32 H32A . 0.9300 ?
C33 C34 . 1.416(4) ?
C33 H33A . 0.9300 ?
C35 H35A . 0.9700 ?
C35 H35B . 0.9700 ?
C36 C37 . 1.493(4) ?
C36 C38 . 1.498(4) ?
C36 H36A . 0.9800 ?
C37 C38 . 1.472(4) ?
C37 H37A . 0.9700 ?
C37 H37B . 0.9700 ?
C38 H38A . 0.9700 ?
C38 H38B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1A N2 3_567 0.85 2.0390 2.849(3) 159
O2 H2B O1 1_455 0.82 2.0990 2.909(3) 170
C30 H30A O1 3_567 0.93 2.5700 3.307(3) 136
C37 H37B O1 3_567 0.97 2.5860 3.372(4) 138
C36 H36A O2 . 0.98 2.4920 3.117(4) 121
C17 H17A O1 . 0.98 2.5520 3.168(4) 121
C12 H12A O2 4_575 0.93 2.423 3.318(5) 161
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F1 C1 C2 C3 . . . . 178.2(3) ?
C6 C1 C2 C3 . . . . -2.3(6) ?
C1 C2 C3 C4 . . . . 0.7(5) ?
C2 C3 C4 C5 . . . . 1.3(5) ?
C2 C3 C4 C7 . . . . -176.4(3) ?
C3 C4 C5 C6 . . . . -1.9(5) ?
C7 C4 C5 C6 . . . . 175.7(3) ?
F1 C1 C6 C5 . . . . -178.8(4) ?
C2 C1 C6 C5 . . . . 1.7(6) ?
C4 C5 C6 C1 . . . . 0.5(6) ?
C5 C4 C7 C8 . . . . -107.4(4) ?
C3 C4 C7 C8 . . . . 70.2(4) ?
C5 C4 C7 C15 . . . . 74.9(4) ?
C3 C4 C7 C15 . . . . -107.6(3) ?
C15 C7 C8 C9 . . . . 2.3(4) ?
C4 C7 C8 C9 . . . . -175.5(3) ?
C15 C7 C8 C16 . . . . -175.6(3) ?
C4 C7 C8 C16 . . . . 6.6(4) ?
C10 N1 C9 C8 . . . . -1.6(5) ?
C10 N1 C9 C17 . . . . 178.9(3) ?
C7 C8 C9 N1 . . . . -0.2(5) ?
C16 C8 C9 N1 . . . . 177.7(3) ?
C7 C8 C9 C17 . . . . 179.3(3) ?
C16 C8 C9 C17 . . . . -2.7(4) ?
C9 N1 C10 C11 . . . . 179.2(3) ?
C9 N1 C10 C15 . . . . 1.3(5) ?
N1 C10 C11 C12 . . . . 180.0(3) ?
C15 C10 C11 C12 . . . . -2.0(5) ?
C10 C11 C12 C13 . . . . 1.5(6) ?
C11 C12 C13 C14 . . . . -0.7(6) ?
C12 C13 C14 C15 . . . . 0.3(5) ?
N1 C10 C15 C14 . . . . 179.5(3) ?
C11 C10 C15 C14 . . . . 1.6(5) ?
N1 C10 C15 C7 . . . . 0.8(5) ?
C11 C10 C15 C7 . . . . -177.2(3) ?
C13 C14 C15 C10 . . . . -0.8(5) ?
C13 C14 C15 C7 . . . . 177.9(3) ?
C8 C7 C15 C10 . . . . -2.5(4) ?
C4 C7 C15 C10 . . . . 175.3(3) ?
C8 C7 C15 C14 . . . . 178.8(3) ?
C4 C7 C15 C14 . . . . -3.4(4) ?
C7 C8 C16 O1 . . . . -106.7(3) ?
C9 C8 C16 O1 . . . . 75.4(3) ?
N1 C9 C17 C18 . . . . 25.2(5) ?
C8 C9 C17 C18 . . . . -154.4(3) ?
N1 C9 C17 C19 . . . . -43.9(5) ?
C8 C9 C17 C19 . . . . 136.5(3) ?
C9 C17 C18 C19 . . . . -107.0(4) ?
C9 C17 C19 C18 . . . . 111.4(4) ?
C25 C20 C21 C22 . . . . -1.5(6) ?
F2 C20 C21 C22 . . . . 178.6(3) ?
C20 C21 C22 C23 . . . . 0.0(5) ?
C21 C22 C23 C24 . . . . 1.2(5) ?
C21 C22 C23 C26 . . . . -176.9(3) ?
C22 C23 C24 C25 . . . . -1.2(5) ?
C26 C23 C24 C25 . . . . 176.9(3) ?
F2 C20 C25 C24 . . . . -178.5(3) ?
C21 C20 C25 C24 . . . . 1.5(6) ?
C23 C24 C25 C20 . . . . -0.1(6) ?
C22 C23 C26 C27 . . . . -75.3(4) ?
C24 C23 C26 C27 . . . . 106.6(4) ?
C22 C23 C26 C34 . . . . 103.1(3) ?
C24 C23 C26 C34 . . . . -75.0(4) ?
C34 C26 C27 C28 . . . . -0.4(4) ?
C23 C26 C27 C28 . . . . 178.0(3) ?
C34 C26 C27 C35 . . . . -179.1(3) ?
C23 C26 C27 C35 . . . . -0.7(4) ?
C29 N2 C28 C27 . . . . 0.1(4) ?
C29 N2 C28 C36 . . . . -179.3(3) ?
C26 C27 C28 N2 . . . . 0.0(4) ?
C35 C27 C28 N2 . . . . 178.7(3) ?
C26 C27 C28 C36 . . . . 179.4(3) ?
C35 C27 C28 C36 . . . . -1.9(4) ?
C28 N2 C29 C34 . . . . 0.1(4) ?
C28 N2 C29 C30 . . . . -178.3(3) ?
N2 C29 C30 C31 . . . . 179.0(3) ?
C34 C29 C30 C31 . . . . 0.6(5) ?
C29 C30 C31 C32 . . . . -0.7(5) ?
C30 C31 C32 C33 . . . . 0.2(5) ?
C31 C32 C33 C34 . . . . 0.3(5) ?
N2 C29 C34 C33 . . . . -178.4(3) ?
C30 C29 C34 C33 . . . . -0.1(4) ?
N2 C29 C34 C26 . . . . -0.4(4) ?
C30 C29 C34 C26 . . . . 177.9(3) ?
C32 C33 C34 C29 . . . . -0.4(4) ?
C32 C33 C34 C26 . . . . -178.3(3) ?
C27 C26 C34 C29 . . . . 0.6(4) ?
C23 C26 C34 C29 . . . . -177.9(2) ?
C27 C26 C34 C33 . . . . 178.5(3) ?
C23 C26 C34 C33 . . . . 0.0(4) ?
C26 C27 C35 O2 . . . . 111.6(3) ?
C28 C27 C35 O2 . . . . -67.0(3) ?
N2 C28 C36 C37 . . . . -29.2(4) ?
C27 C28 C36 C37 . . . . 151.3(3) ?
N2 C28 C36 C38 . . . . 41.0(4) ?
C27 C28 C36 C38 . . . . -138.4(3) ?
C28 C36 C37 C38 . . . . 108.6(3) ?
C28 C36 C38 C37 . . . . -111.5(3) ?
