#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/88/2228891.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2228891
loop_
_publ_author_name
'Pastrán, Jesús'
'Ineichen, Emilio'
'Agrifoglio, Giuseppe'
'Linden, Anthony'
'Dorta, Romano'
_publ_section_title
;
 (E)-3-(1-Naphthylamino)methylene-(+)-camphor
;
_journal_coeditor_code           SU2235
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o188
_journal_page_last               o189
_journal_paper_doi               10.1107/S1600536810052487
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H23 N O'
_chemical_formula_moiety         'C21 H23 N O'
_chemical_formula_sum            'C21 H23 N O'
_chemical_formula_weight         305.42
_chemical_melting_point          352
_chemical_name_common
;
(E)-3-(1-naphthylamino)methylene-(+)-camphor
;
_chemical_name_systematic
;
(E)-1,7,7-trimethyl-3-[(1-
naphthylamino)methylidene]bicyclo[2.2.1]heptan-2-one
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.672(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.807(2)
_cell_length_b                   11.9688(12)
_cell_length_c                   12.0192(8)
_cell_measurement_reflns_used    3158
_cell_measurement_temperature    160.0(10)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     3408.0(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      160.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21618
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.0722
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.170
_refine_ls_abs_structure_details 'none; 2643 Friedel pairs merged'
_refine_ls_extinction_coef       0.0040(7)
_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   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0737P)²+1.1311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                2227
_reflns_number_total             3170
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2235.cif
_cod_data_source_block           I
_cod_original_cell_volume        3408.1(5)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2228891
_cod_database_fobs_code          2228891
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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
O O1 0.68329(13) 0.4955(3) 0.5734(2) 0.0597(10) Uani d . 1 . .
N N1 0.76542(16) 0.5821(4) 0.2820(3) 0.0467(10) Uani d . 1 . .
H H1 0.7453(18) 0.563(4) 0.204(4) 0.056 Uiso d . 1 . .
C C1 0.82420(18) 0.6018(4) 0.2844(4) 0.0457(12) Uani d . 1 . .
C C2 0.8445(2) 0.6690(4) 0.1988(4) 0.0454(12) Uani d . 1 . .
C C3 0.8088(2) 0.7267(5) 0.1164(4) 0.0542(14) Uani d . 1 . .
H H3 0.7691 0.7240 0.1190 0.065 Uiso calc R 1 . .
C C4 0.8307(2) 0.7866(5) 0.0329(4) 0.0624(15) Uani d . 1 . .
H H4 0.8064 0.8257 -0.0211 0.075 Uiso calc R 1 . .
C C5 0.8888(3) 0.7892(5) 0.0282(5) 0.0674(16) Uani d . 1 . .
H H5 0.9036 0.8278 -0.0316 0.081 Uiso calc R 1 . .
C C6 0.9245(2) 0.7388(5) 0.1057(4) 0.0584(15) Uani d . 1 . .
H H6 0.9641 0.7438 0.1009 0.070 Uiso calc R 1 . .
C C7 0.9041(2) 0.6780(5) 0.1950(4) 0.0508(13) Uani d . 1 . .
C C8 0.9406(2) 0.6296(5) 0.2821(5) 0.0575(14) Uani d . 1 . .
H H8 0.9802 0.6378 0.2817 0.069 Uiso calc R 1 . .
C C9 0.9198(2) 0.5715(5) 0.3664(4) 0.0569(13) Uani d . 1 . .
H H9 0.9449 0.5412 0.4251 0.068 Uiso calc R 1 . .
C C10 0.86094(19) 0.5562(4) 0.3669(4) 0.0514(13) Uani d . 1 . .
H H10 0.8468 0.5140 0.4250 0.062 Uiso calc R 1 . .
C C11 0.74053(18) 0.5505(4) 0.3731(4) 0.0435(12) Uani d . 1 . .
H H11 0.7592 0.5701 0.4439 0.052 Uiso calc R 1 . .
C C12 0.69145(18) 0.4934(4) 0.3731(3) 0.0436(12) Uani d . 1 . .
C C13 0.65587(19) 0.4306(4) 0.2821(3) 0.0454(12) Uani d . 1 . .
H H13 0.6557 0.4624 0.2051 0.054 Uiso calc R 1 . .
C C14 0.6757(2) 0.3084(4) 0.2953(4) 0.0574(14) Uani d . 1 . .
H H141 0.7173 0.3028 0.2978 0.069 Uiso calc R 1 . .
H H142 0.6583 0.2611 0.2336 0.069 Uiso calc R 1 . .
C C15 0.6547(2) 0.2746(5) 0.4094(4) 0.0595(14) Uani d . 1 . .
H H151 0.6869 0.2576 0.4654 0.071 Uiso calc R 1 . .
H H152 0.6297 0.2084 0.4008 0.071 Uiso calc R 1 . .
C C16 0.62158(19) 0.3793(4) 0.4453(3) 0.0469(12) Uani d . 1 . .
C C17 0.66827(19) 0.4636(4) 0.4773(4) 0.0467(13) Uani d . 1 . .
C C18 0.59773(18) 0.4275(4) 0.3300(3) 0.0459(12) Uani d . 1 . .
C C19 0.5713(2) 0.5429(5) 0.3385(4) 0.0590(14) Uani d . 1 . .
H H191 0.5393 0.5382 0.3836 0.088 Uiso calc R 1 . .
H H192 0.5581 0.5699 0.2634 0.088 Uiso calc R 1 . .
H H193 0.5995 0.5948 0.3738 0.088 Uiso calc R 1 . .
C C20 0.5540(2) 0.3515(5) 0.2652(4) 0.0624(15) Uani d . 1 . .
H H201 0.5440 0.3824 0.1903 0.094 Uiso calc R 1 . .
H H202 0.5202 0.3469 0.3051 0.094 Uiso calc R 1 . .
H H203 0.5700 0.2766 0.2586 0.094 Uiso calc R 1 . .
C C21 0.5823(2) 0.3569(6) 0.5342(4) 0.0631(15) Uani d . 1 . .
H H211 0.5603 0.4243 0.5460 0.095 Uiso calc R 1 . .
H H212 0.6044 0.3362 0.6042 0.095 Uiso calc R 1 . .
H H213 0.5566 0.2956 0.5099 0.095 Uiso calc R 1 . .
O O2 0.69132(15) 0.5802(3) 1.0744(3) 0.0673(11) Uani d . 1 . .
N N2 0.76421(18) 0.5057(4) 0.7714(3) 0.0564(12) Uani d . 1 . .
H H2 0.743(2) 0.502(5) 0.712(4) 0.068 Uiso d . 1 . .
C C31 0.8225(2) 0.4882(5) 0.7702(4) 0.0512(13) Uani d . 1 . .
C C32 0.8415(2) 0.4213(5) 0.6840(4) 0.0554(14) Uani d . 1 . .
C C33 0.8049(2) 0.3591(5) 0.6054(4) 0.0588(14) Uani d . 1 . .
H H33 0.7653 0.3617 0.6100 0.071 Uiso calc R 1 . .
C C34 0.8253(3) 0.2968(5) 0.5246(5) 0.0674(16) Uani d . 1 . .
H H34 0.7998 0.2569 0.4732 0.081 Uiso calc R 1 . .
C C35 0.8829(3) 0.2900(6) 0.5154(5) 0.0750(17) Uani d . 1 . .
H H35 0.8965 0.2475 0.4569 0.090 Uiso calc R 1 . .
C C36 0.9189(3) 0.3432(5) 0.5889(5) 0.0700(16) Uani d . 1 . .
H H36 0.9582 0.3376 0.5822 0.084 Uiso calc R 1 . .
C C37 0.8998(2) 0.4094(5) 0.6788(5) 0.0572(14) Uani d . 1 . .
C C38 0.9397(2) 0.4604(5) 0.7578(5) 0.0621(15) Uani d . 1 . .
H H38 0.9791 0.4515 0.7537 0.075 Uiso calc R 1 . .
C C39 0.9195(2) 0.5234(5) 0.8409(5) 0.0708(17) Uani d . 1 . .
H H39 0.9455 0.5581 0.8952 0.085 Uiso calc R 1 . .
C C40 0.8608(2) 0.5376(5) 0.8472(4) 0.0582(14) Uani d . 1 . .
H H40 0.8480 0.5817 0.9054 0.070 Uiso calc R 1 . .
C C41 0.7408(2) 0.5355(5) 0.8651(4) 0.0575(14) Uani d . 1 . .
H H41 0.7626 0.5197 0.9339 0.069 Uiso calc R 1 . .
C C42 0.68961(18) 0.5857(4) 0.8730(4) 0.0452(12) Uani d . 1 . .
C C43 0.6461(2) 0.6346(5) 0.7896(4) 0.0547(14) Uani d . 1 . .
H H43 0.6592 0.6503 0.7146 0.066 Uiso calc R 1 . .
C C44 0.5941(2) 0.5569(6) 0.7881(4) 0.0674(16) Uani d . 1 . .
H H441 0.5651 0.5764 0.7263 0.081 Uiso calc R 1 . .
H H442 0.6049 0.4775 0.7811 0.081 Uiso calc R 1 . .
C C45 0.5733(2) 0.5810(5) 0.9029(4) 0.0621(14) Uani d . 1 . .
H H451 0.5747 0.5127 0.9495 0.075 Uiso calc R 1 . .
H H452 0.5341 0.6097 0.8944 0.075 Uiso calc R 1 . .
C C46 0.6151(2) 0.6717(5) 0.9562(4) 0.0524(13) Uani d . 1 . .
C C47 0.6699(2) 0.6078(4) 0.9813(4) 0.0458(12) Uani d . 1 . .
C C48 0.62762(19) 0.7388(5) 0.8533(4) 0.0556(14) Uani d . 1 . .
C C49 0.6746(2) 0.8251(5) 0.8770(5) 0.0661(15) Uani d . 1 . .
H H491 0.6821 0.8616 0.8070 0.099 Uiso calc R 1 . .
H H492 0.7090 0.7877 0.9098 0.099 Uiso calc R 1 . .
H H493 0.6630 0.8812 0.9295 0.099 Uiso calc R 1 . .
C C50 0.5761(2) 0.8006(6) 0.7922(5) 0.0802(18) Uani d . 1 . .
H H501 0.5461 0.7466 0.7704 0.120 Uiso calc R 1 . .
H H502 0.5875 0.8377 0.7253 0.120 Uiso calc R 1 . .
H H503 0.5622 0.8565 0.8423 0.120 Uiso calc R 1 . .
C C51 0.5939(3) 0.7335(6) 1.0546(4) 0.0796(18) Uani d . 1 . .
H H511 0.6229 0.7860 1.0858 0.119 Uiso calc R 1 . .
H H512 0.5857 0.6796 1.1123 0.119 Uiso calc R 1 . .
H H513 0.5594 0.7747 1.0292 0.119 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 for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
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
C11 N1 C1 . . 122.8(4) ?
C11 N1 H1 . . 118(3) ?
C1 N1 H1 . . 115(2) ?
C10 C1 N1 . . 120.5(4) ?
C10 C1 C2 . . 120.6(4) ?
N1 C1 C2 . . 118.9(4) ?
C3 C2 C1 . . 123.7(4) ?
C3 C2 C7 . . 118.0(5) ?
C1 C2 C7 . . 118.3(5) ?
C4 C3 C2 . . 121.2(5) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C3 C4 C5 . . 119.4(5) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
C6 C5 C4 . . 121.8(5) ?
C6 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
C5 C6 C7 . . 121.0(5) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C8 C7 C6 . . 122.5(5) ?
C8 C7 C2 . . 118.9(5) ?
C6 C7 C2 . . 118.5(5) ?
C9 C8 C7 . . 121.3(5) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C8 C9 C10 . . 120.1(5) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C1 C10 C9 . . 120.5(5) ?
C1 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
N1 C11 C12 . . 126.1(4) ?
N1 C11 H11 . . 116.9 ?
C12 C11 H11 . . 116.9 ?
C11 C12 C17 . . 121.5(4) ?
C11 C12 C13 . . 132.2(4) ?
C17 C12 C13 . . 105.4(4) ?
C12 C13 C14 . . 104.7(4) ?
C12 C13 C18 . . 101.5(3) ?
C14 C13 C18 . . 102.4(4) ?
C12 C13 H13 . . 115.5 ?
C14 C13 H13 . . 115.5 ?
C18 C13 H13 . . 115.5 ?
C13 C14 C15 . . 102.4(4) ?
C13 C14 H141 . . 111.3 ?
C15 C14 H141 . . 111.3 ?
C13 C14 H142 . . 111.3 ?
C15 C14 H142 . . 111.3 ?
H141 C14 H142 . . 109.2 ?
C14 C15 C16 . . 104.5(4) ?
C14 C15 H151 . . 110.9 ?
C16 C15 H151 . . 110.9 ?
C14 C15 H152 . . 110.9 ?
C16 C15 H152 . . 110.9 ?
H151 C15 H152 . . 108.9 ?
C21 C16 C17 . . 115.2(4) ?
C21 C16 C18 . . 119.9(4) ?
C17 C16 C18 . . 99.9(4) ?
C21 C16 C15 . . 114.7(5) ?
C17 C16 C15 . . 103.0(4) ?
C18 C16 C15 . . 101.6(4) ?
O1 C17 C12 . . 128.8(5) ?
O1 C17 C16 . . 125.3(4) ?
C12 C17 C16 . . 105.9(4) ?
C19 C18 C20 . . 107.9(4) ?
C19 C18 C13 . . 113.1(4) ?
C20 C18 C13 . . 114.2(4) ?
C19 C18 C16 . . 113.2(4) ?
C20 C18 C16 . . 113.7(4) ?
C13 C18 C16 . . 94.5(3) ?
C18 C19 H191 . . 109.5 ?
C18 C19 H192 . . 109.5 ?
H191 C19 H192 . . 109.5 ?
C18 C19 H193 . . 109.5 ?
H191 C19 H193 . . 109.5 ?
H192 C19 H193 . . 109.5 ?
C18 C20 H201 . . 109.5 ?
C18 C20 H202 . . 109.5 ?
H201 C20 H202 . . 109.5 ?
C18 C20 H203 . . 109.5 ?
H201 C20 H203 . . 109.5 ?
H202 C20 H203 . . 109.5 ?
C16 C21 H211 . . 109.5 ?
C16 C21 H212 . . 109.5 ?
H211 C21 H212 . . 109.5 ?
C16 C21 H213 . . 109.5 ?
H211 C21 H213 . . 109.5 ?
H212 C21 H213 . . 109.5 ?
C41 N2 C31 . . 122.4(4) ?
C41 N2 H2 . . 117(4) ?
C31 N2 H2 . . 120(4) ?
C40 C31 N2 . . 121.5(5) ?
C40 C31 C32 . . 119.9(5) ?
N2 C31 C32 . . 118.6(4) ?
C37 C32 C31 . . 118.6(5) ?
C37 C32 C33 . . 117.4(5) ?
C31 C32 C33 . . 124.0(5) ?
C34 C33 C32 . . 121.5(5) ?
C34 C33 H33 . . 119.2 ?
C32 C33 H33 . . 119.2 ?
C33 C34 C35 . . 121.1(6) ?
C33 C34 H34 . . 119.4 ?
C35 C34 H34 . . 119.4 ?
C36 C35 C34 . . 119.7(6) ?
C36 C35 H35 . . 120.1 ?
C34 C35 H35 . . 120.1 ?
C35 C36 C37 . . 121.9(6) ?
C35 C36 H36 . . 119.1 ?
C37 C36 H36 . . 119.1 ?
C32 C37 C38 . . 121.9(5) ?
C32 C37 C36 . . 118.2(5) ?
C38 C37 C36 . . 119.9(5) ?
C39 C38 C37 . . 117.7(5) ?
C39 C38 H38 . . 121.1 ?
C37 C38 H38 . . 121.1 ?
C38 C39 C40 . . 121.5(5) ?
C38 C39 H39 . . 119.3 ?
C40 C39 H39 . . 119.3 ?
C31 C40 C39 . . 120.5(5) ?
C31 C40 H40 . . 119.8 ?
C39 C40 H40 . . 119.8 ?
N2 C41 C42 . . 128.0(5) ?
N2 C41 H41 . . 116.0 ?
C42 C41 H41 . . 116.0 ?
C41 C42 C47 . . 120.8(4) ?
C41 C42 C43 . . 133.6(4) ?
C47 C42 C43 . . 105.5(4) ?
C42 C43 C44 . . 105.9(4) ?
C42 C43 C48 . . 101.3(4) ?
C44 C43 C48 . . 102.9(4) ?
C42 C43 H43 . . 115.0 ?
C44 C43 H43 . . 115.0 ?
C48 C43 H43 . . 115.0 ?
C45 C44 C43 . . 101.8(4) ?
C45 C44 H441 . . 111.4 ?
C43 C44 H441 . . 111.4 ?
C45 C44 H442 . . 111.4 ?
C43 C44 H442 . . 111.4 ?
H441 C44 H442 . . 109.3 ?
C44 C45 C46 . . 104.4(4) ?
C44 C45 H451 . . 110.9 ?
C46 C45 H451 . . 110.9 ?
C44 C45 H452 . . 110.9 ?
C46 C45 H452 . . 110.9 ?
H451 C45 H452 . . 108.9 ?
C47 C46 C51 . . 115.8(4) ?
C47 C46 C48 . . 101.1(4) ?
C51 C46 C48 . . 118.6(5) ?
C47 C46 C45 . . 103.4(4) ?
C51 C46 C45 . . 114.1(4) ?
C48 C46 C45 . . 101.6(4) ?
O2 C47 C42 . . 128.7(5) ?
O2 C47 C46 . . 126.1(4) ?
C42 C47 C46 . . 105.2(4) ?
C46 C48 C49 . . 113.7(4) ?
C46 C48 C43 . . 93.7(4) ?
C49 C48 C43 . . 113.4(4) ?
C46 C48 C50 . . 115.1(4) ?
C49 C48 C50 . . 107.2(5) ?
C43 C48 C50 . . 113.5(4) ?
C48 C49 H491 . . 109.5 ?
C48 C49 H492 . . 109.5 ?
H491 C49 H492 . . 109.5 ?
C48 C49 H493 . . 109.5 ?
H491 C49 H493 . . 109.5 ?
H492 C49 H493 . . 109.5 ?
C48 C50 H501 . . 109.5 ?
C48 C50 H502 . . 109.5 ?
H501 C50 H502 . . 109.5 ?
C48 C50 H503 . . 109.5 ?
H501 C50 H503 . . 109.5 ?
H502 C50 H503 . . 109.5 ?
C46 C51 H511 . . 109.5 ?
C46 C51 H512 . . 109.5 ?
H511 C51 H512 . . 109.5 ?
C46 C51 H513 . . 109.5 ?
H511 C51 H513 . . 109.5 ?
H512 C51 H513 . . 109.5 ?
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
O1 C17 . 1.235(5) ?
N1 C11 . 1.351(6) ?
N1 C1 . 1.416(6) ?
N1 H1 . 1.03(4) ?
C1 C10 . 1.370(6) ?
C1 C2 . 1.427(6) ?
C2 C3 . 1.419(7) ?
C2 C7 . 1.429(6) ?
C3 C4 . 1.378(7) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.391(8) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.341(8) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.421(7) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.416(7) ?
C8 C9 . 1.362(7) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.414(6) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 C12 . 1.353(6) ?
C11 H11 . 0.9500 ?
C12 C17 . 1.462(6) ?
C12 C13 . 1.516(6) ?
C13 C14 . 1.541(7) ?
C13 C18 . 1.551(6) ?
C13 H13 . 1.0000 ?
C14 C15 . 1.559(7) ?
C14 H141 . 0.9900 ?
C14 H142 . 0.9900 ?
C15 C16 . 1.563(7) ?
C15 H151 . 0.9900 ?
C15 H152 . 0.9900 ?
C16 C21 . 1.512(6) ?
C16 C17 . 1.522(7) ?
C16 C18 . 1.555(6) ?
C18 C19 . 1.526(7) ?
C18 C20 . 1.535(6) ?
C19 H191 . 0.9800 ?
C19 H192 . 0.9800 ?
C19 H193 . 0.9800 ?
C20 H201 . 0.9800 ?
C20 H202 . 0.9800 ?
C20 H203 . 0.9800 ?
C21 H211 . 0.9800 ?
C21 H212 . 0.9800 ?
C21 H213 . 0.9800 ?
O2 C47 . 1.229(5) ?
N2 C41 . 1.353(6) ?
N2 C31 . 1.404(6) ?
N2 H2 . 0.83(5) ?
C31 C40 . 1.368(7) ?
C31 C32 . 1.419(7) ?
C32 C37 . 1.404(7) ?
C32 C33 . 1.430(7) ?
C33 C34 . 1.353(7) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.390(8) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.331(8) ?
C35 H35 . 0.9500 ?
C36 C37 . 1.449(8) ?
C36 H36 . 0.9500 ?
C37 C38 . 1.413(8) ?
C38 C39 . 1.375(7) ?
C38 H38 . 0.9500 ?
C39 C40 . 1.418(7) ?
C39 H39 . 0.9500 ?
C40 H40 . 0.9500 ?
C41 C42 . 1.371(7) ?
C41 H41 . 0.9500 ?
C42 C47 . 1.451(6) ?
C42 C43 . 1.488(6) ?
C43 C44 . 1.547(8) ?
C43 C48 . 1.551(7) ?
C43 H43 . 1.0000 ?
C44 C45 . 1.540(7) ?
C44 H441 . 0.9900 ?
C44 H442 . 0.9900 ?
C45 C46 . 1.566(8) ?
C45 H451 . 0.9900 ?
C45 H452 . 0.9900 ?
C46 C47 . 1.516(7) ?
C46 C51 . 1.523(7) ?
C46 C48 . 1.528(7) ?
C48 C49 . 1.529(7) ?
C48 C50 . 1.553(7) ?
C49 H491 . 0.9800 ?
C49 H492 . 0.9800 ?
C49 H493 . 0.9800 ?
C50 H501 . 0.9800 ?
C50 H502 . 0.9800 ?
C50 H503 . 0.9800 ?
C51 H511 . 0.9800 ?
C51 H512 . 0.9800 ?
C51 H513 . 0.9800 ?
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
_geom_hbond_publ_flag
N1 H1 O2 1_554 1.03(4) 1.93(4) 2.909(5) 157(4) yes
N2 H2 O1 . 0.83(5) 2.08(5) 2.913(5) 174(5) yes
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
C11 N1 C1 C10 . . . . 21.3(7) ?
C11 N1 C1 C2 . . . . -159.3(4) ?
C10 C1 C2 C3 . . . . -174.3(5) ?
N1 C1 C2 C3 . . . . 6.2(7) ?
C10 C1 C2 C7 . . . . 6.2(7) ?
N1 C1 C2 C7 . . . . -173.2(4) ?
C1 C2 C3 C4 . . . . -177.2(5) ?
C7 C2 C3 C4 . . . . 2.2(7) ?
C2 C3 C4 C5 . . . . 0.9(8) ?
C3 C4 C5 C6 . . . . -2.8(9) ?
C4 C5 C6 C7 . . . . 1.5(9) ?
C5 C6 C7 C8 . . . . -176.0(5) ?
C5 C6 C7 C2 . . . . 1.7(8) ?
C3 C2 C7 C8 . . . . 174.3(5) ?
C1 C2 C7 C8 . . . . -6.2(7) ?
C3 C2 C7 C6 . . . . -3.5(7) ?
C1 C2 C7 C6 . . . . 176.0(4) ?
C6 C7 C8 C9 . . . . -179.8(5) ?
C2 C7 C8 C9 . . . . 2.5(8) ?
C7 C8 C9 C10 . . . . 1.5(8) ?
N1 C1 C10 C9 . . . . 177.1(5) ?
C2 C1 C10 C9 . . . . -2.4(8) ?
C8 C9 C10 C1 . . . . -1.6(8) ?
C1 N1 C11 C12 . . . . -155.0(5) ?
N1 C11 C12 C17 . . . . -179.9(5) ?
N1 C11 C12 C13 . . . . 12.9(9) ?
C11 C12 C13 C14 . . . . 94.2(6) ?
C17 C12 C13 C14 . . . . -74.5(4) ?
C11 C12 C13 C18 . . . . -159.5(5) ?
C17 C12 C13 C18 . . . . 31.8(5) ?
C12 C13 C14 C15 . . . . 67.9(4) ?
C18 C13 C14 C15 . . . . -37.7(4) ?
C13 C14 C15 C16 . . . . 3.6(5) ?
C14 C15 C16 C21 . . . . 162.2(4) ?
C14 C15 C16 C17 . . . . -71.8(4) ?
C14 C15 C16 C18 . . . . 31.4(5) ?
C11 C12 C17 O1 . . . . 10.6(8) ?
C13 C12 C17 O1 . . . . -179.2(5) ?
C11 C12 C17 C16 . . . . -167.4(5) ?
C13 C12 C17 C16 . . . . 2.8(5) ?
C21 C16 C17 O1 . . . . 15.9(7) ?
C18 C16 C17 O1 . . . . 145.8(5) ?
C15 C16 C17 O1 . . . . -109.7(5) ?
C21 C16 C17 C12 . . . . -166.0(4) ?
C18 C16 C17 C12 . . . . -36.1(5) ?
C15 C16 C17 C12 . . . . 68.4(4) ?
C12 C13 C18 C19 . . . . 65.7(5) ?
C14 C13 C18 C19 . . . . 173.7(4) ?
C12 C13 C18 C20 . . . . -170.4(4) ?
C14 C13 C18 C20 . . . . -62.4(5) ?
C12 C13 C18 C16 . . . . -51.9(4) ?
C14 C13 C18 C16 . . . . 56.2(4) ?
C21 C16 C18 C19 . . . . 62.3(6) ?
C17 C16 C18 C19 . . . . -64.5(4) ?
C15 C16 C18 C19 . . . . -170.2(4) ?
C21 C16 C18 C20 . . . . -61.2(6) ?
C17 C16 C18 C20 . . . . 171.9(4) ?
C15 C16 C18 C20 . . . . 66.3(5) ?
C21 C16 C18 C13 . . . . 179.8(5) ?
C17 C16 C18 C13 . . . . 53.0(4) ?
C15 C16 C18 C13 . . . . -52.7(4) ?
C41 N2 C31 C40 . . . . -24.4(8) ?
C41 N2 C31 C32 . . . . 158.1(5) ?
C40 C31 C32 C37 . . . . -1.3(7) ?
N2 C31 C32 C37 . . . . 176.1(5) ?
C40 C31 C32 C33 . . . . 174.7(5) ?
N2 C31 C32 C33 . . . . -7.8(8) ?
C37 C32 C33 C34 . . . . -4.1(7) ?
C31 C32 C33 C34 . . . . 179.9(5) ?
C32 C33 C34 C35 . . . . 0.5(8) ?
C33 C34 C35 C36 . . . . 1.8(9) ?
C34 C35 C36 C37 . . . . -0.4(9) ?
C31 C32 C37 C38 . . . . 1.2(8) ?
C33 C32 C37 C38 . . . . -175.2(5) ?
C31 C32 C37 C36 . . . . -178.5(5) ?
C33 C32 C37 C36 . . . . 5.2(7) ?
C35 C36 C37 C32 . . . . -3.1(8) ?
C35 C36 C37 C38 . . . . 177.2(6) ?
C32 C37 C38 C39 . . . . -0.3(8) ?
C36 C37 C38 C39 . . . . 179.3(5) ?
C37 C38 C39 C40 . . . . -0.4(8) ?
N2 C31 C40 C39 . . . . -176.7(5) ?
C32 C31 C40 C39 . . . . 0.7(8) ?
C38 C39 C40 C31 . . . . 0.2(9) ?
C31 N2 C41 C42 . . . . 159.3(5) ?
N2 C41 C42 C47 . . . . 177.4(5) ?
N2 C41 C42 C43 . . . . -7.6(10) ?
C41 C42 C43 C44 . . . . 112.2(6) ?
C47 C42 C43 C44 . . . . -72.2(5) ?
C41 C42 C43 C48 . . . . -140.7(6) ?
C47 C42 C43 C48 . . . . 34.8(5) ?
C42 C43 C44 C45 . . . . 70.0(5) ?
C48 C43 C44 C45 . . . . -35.9(5) ?
C43 C44 C45 C46 . . . . 1.1(5) ?
C44 C45 C46 C47 . . . . -70.1(5) ?
C44 C45 C46 C51 . . . . 163.3(5) ?
C44 C45 C46 C48 . . . . 34.5(5) ?
C41 C42 C47 O2 . . . . -5.9(9) ?
C43 C42 C47 O2 . . . . 177.8(5) ?
C41 C42 C47 C46 . . . . 175.3(5) ?
C43 C42 C47 C46 . . . . -0.9(6) ?
C51 C46 C47 O2 . . . . 17.8(8) ?
C48 C46 C47 O2 . . . . 147.4(5) ?
C45 C46 C47 O2 . . . . -107.8(6) ?
C51 C46 C47 C42 . . . . -163.4(5) ?
C48 C46 C47 C42 . . . . -33.8(5) ?
C45 C46 C47 C42 . . . . 71.0(5) ?
C47 C46 C48 C49 . . . . -65.4(5) ?
C51 C46 C48 C49 . . . . 62.4(6) ?
C45 C46 C48 C49 . . . . -171.7(4) ?
C47 C46 C48 C43 . . . . 52.2(4) ?
C51 C46 C48 C43 . . . . 179.9(5) ?
C45 C46 C48 C43 . . . . -54.2(4) ?
C47 C46 C48 C50 . . . . 170.3(5) ?
C51 C46 C48 C50 . . . . -61.9(7) ?
C45 C46 C48 C50 . . . . 64.0(6) ?
C42 C43 C48 C46 . . . . -53.2(4) ?
C44 C43 C48 C46 . . . . 56.2(4) ?
C42 C43 C48 C49 . . . . 64.7(5) ?
C44 C43 C48 C49 . . . . 174.1(4) ?
C42 C43 C48 C50 . . . . -172.7(4) ?
C44 C43 C48 C50 . . . . -63.3(5) ?
