#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/31/2233190.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_2233190
loop_
_publ_author_name
'Choi, Jong-Ha'
'Subhan, Md Abdus'
'Ryoo, Keon Sang'
'Ng, Seik Weng'
_publ_section_title
;
 3,14-Dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12^]docosane--(naphthalen-1-yl)methanol
 (1/2)
;
_journal_coeditor_code           HG5151
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o102
_journal_paper_doi               10.1107/S160053681105272X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H40 N4, 2C11 H10 O'
_chemical_formula_moiety         'C20 H40 N4, 2(C11 H10 O)'
_chemical_formula_sum            'C42 H60 N4 O2'
_chemical_formula_weight         652.94
_chemical_name_systematic
;
3,14-Dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12^]docosane--
(naphthalen-1-yl)methanol (1/2)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.500(4)
_cell_angle_beta                 97.961(4)
_cell_angle_gamma                96.666(4)
_cell_formula_units_Z            1
_cell_length_a                   8.9706(4)
_cell_length_b                   9.4967(6)
_cell_length_c                   10.5580(5)
_cell_measurement_reflns_used    2968
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2500
_cell_measurement_theta_min      2.7947
_cell_volume                     883.13(8)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6926
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0516P)²+0.3587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                2958
_reflns_number_total             3915
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5151.cif
_cod_data_source_block           I
_cod_database_code               2233190
_cod_database_fobs_code          2233190
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
O O1 0.39115(13) 0.38946(12) 0.62565(11) 0.0246(3) Uani d D 1 1
N N1 0.10202(14) 0.30725(14) 0.49130(12) 0.0167(3) Uani d D 1 1
N N2 0.02690(14) 0.51309(13) 0.31361(12) 0.0169(3) Uani d D 1 1
C C1 0.04567(17) 0.24648(16) 0.70859(14) 0.0187(3) Uani d . 1 1
H H1A 0.1503 0.2922 0.7383 0.022 Uiso calc R 1 1
H H1B 0.0293 0.1613 0.7582 0.022 Uiso calc R 1 1
C C2 0.03614(18) 0.19676(16) 0.56804(14) 0.0195(3) Uani d . 1 1
H H2A 0.0903 0.1121 0.5622 0.023 Uiso calc R 1 1
H H2B -0.0715 0.1684 0.5318 0.023 Uiso calc R 1 1
C C3 0.07600(16) 0.26812(16) 0.35267(14) 0.0165(3) Uani d . 1 1
H H3 -0.0335 0.2310 0.3268 0.020 Uiso calc R 1 1
C C4 0.17260(18) 0.15236(17) 0.32043(15) 0.0218(3) Uani d . 1 1
H H4A 0.2808 0.1862 0.3509 0.026 Uiso calc R 1 1
H H4B 0.1442 0.0668 0.3663 0.026 Uiso calc R 1 1
C C5 0.1525(2) 0.11239(18) 0.17690(16) 0.0274(4) Uani d . 1 1
H H5A 0.2219 0.0422 0.1601 0.033 Uiso calc R 1 1
H H5B 0.0473 0.0678 0.1481 0.033 Uiso calc R 1 1
C C6 0.18552(19) 0.24225(18) 0.10128(15) 0.0238(4) Uani d . 1 1
H H6A 0.1632 0.2150 0.0084 0.029 Uiso calc R 1 1
H H6B 0.2943 0.2797 0.1216 0.029 Uiso calc R 1 1
C C7 0.08938(17) 0.35713(17) 0.13392(14) 0.0191(3) Uani d . 1 1
H H7A -0.0191 0.3223 0.1059 0.023 Uiso calc R 1 1
H H7B 0.1155 0.4420 0.0865 0.023 Uiso calc R 1 1
C C8 0.11388(16) 0.39903(16) 0.27810(14) 0.0161(3) Uani d . 1 1
H H8 0.2240 0.4336 0.3040 0.019 Uiso calc R 1 1
C C9 0.06375(17) 0.65060(16) 0.25732(14) 0.0178(3) Uani d . 1 1
H H9 0.0493 0.6339 0.1620 0.021 Uiso calc R 1 1
C C10 0.22827(17) 0.71117(17) 0.30174(16) 0.0237(4) Uani d . 1 1
H H10A 0.2950 0.6423 0.2792 0.036 Uiso calc R 1 1
H H10B 0.2441 0.7308 0.3948 0.036 Uiso calc R 1 1
H H10C 0.2516 0.7994 0.2598 0.036 Uiso calc R 1 1
C C11 0.40299(19) 0.53897(17) 0.62006(16) 0.0249(4) Uani d . 1 1
H H11A 0.3248 0.5626 0.5512 0.030 Uiso calc R 1 1
H H11B 0.5035 0.5735 0.5968 0.030 Uiso calc R 1 1
C C12 0.38426(16) 0.61640(17) 0.74368(15) 0.0201(3) Uani d . 1 1
C C13 0.36862(17) 0.54546(18) 0.85219(15) 0.0220(3) Uani d . 1 1
H H13 0.3698 0.4455 0.8498 0.026 Uiso calc R 1 1
C C14 0.35081(18) 0.61807(19) 0.96724(16) 0.0256(4) Uani d . 1 1
H H14 0.3424 0.5668 1.0417 0.031 Uiso calc R 1 1
C C15 0.34556(18) 0.76033(19) 0.97311(16) 0.0257(4) Uani d . 1 1
H H15 0.3314 0.8074 1.0510 0.031 Uiso calc R 1 1
C C16 0.36112(17) 0.83948(17) 0.86337(15) 0.0217(3) Uani d . 1 1
C C17 0.35874(19) 0.98840(19) 0.86739(17) 0.0276(4) Uani d . 1 1
H H17 0.3427 1.0366 0.9442 0.033 Uiso calc R 1 1
C C18 0.37914(18) 1.06392(19) 0.76259(17) 0.0291(4) Uani d . 1 1
H H18 0.3779 1.1639 0.7669 0.035 Uiso calc R 1 1
C C19 0.40194(18) 0.99358(18) 0.64866(16) 0.0264(4) Uani d . 1 1
H H19 0.4160 1.0463 0.5759 0.032 Uiso calc R 1 1
C C20 0.40408(17) 0.84951(18) 0.64119(15) 0.0230(4) Uani d . 1 1
H H20 0.4200 0.8038 0.5632 0.028 Uiso calc R 1 1
C C21 0.38299(16) 0.76716(17) 0.74774(15) 0.0195(3) Uani d . 1 1
H H1O 0.3056(15) 0.356(2) 0.5834(18) 0.047(6) Uiso d D 1 1
H H1N 0.0599(18) 0.3847(13) 0.5061(17) 0.027(5) Uiso d D 1 1
H H2N -0.0694(12) 0.4833(19) 0.2849(16) 0.028(5) Uiso d D 1 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'
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
C11 O1 H1O . . 107.1(15)
C2 N1 C3 . . 113.32(11)
C2 N1 H1N . . 107.1(12)
C3 N1 H1N . . 109.4(12)
C8 N2 C9 . . 115.46(11)
C8 N2 H2N . . 106.5(12)
C9 N2 H2N . . 106.9(12)
C2 C1 C9 . 2_566 117.65(13)
C2 C1 H1A . . 107.9
C9 C1 H1A 2_566 . 107.9
C2 C1 H1B . . 107.9
C9 C1 H1B 2_566 . 107.9
H1A C1 H1B . . 107.2
N1 C2 C1 . . 112.57(12)
N1 C2 H2A . . 109.1
C1 C2 H2A . . 109.1
N1 C2 H2B . . 109.1
C1 C2 H2B . . 109.1
H2A C2 H2B . . 107.8
N1 C3 C8 . . 109.94(11)
N1 C3 C4 . . 110.78(13)
C8 C3 C4 . . 109.82(12)
N1 C3 H3 . . 108.8
C8 C3 H3 . . 108.8
C4 C3 H3 . . 108.8
C5 C4 C3 . . 112.30(14)
C5 C4 H4A . . 109.1
C3 C4 H4A . . 109.1
C5 C4 H4B . . 109.1
C3 C4 H4B . . 109.1
H4A C4 H4B . . 107.9
C6 C5 C4 . . 111.15(13)
C6 C5 H5A . . 109.4
C4 C5 H5A . . 109.4
C6 C5 H5B . . 109.4
C4 C5 H5B . . 109.4
H5A C5 H5B . . 108.0
C5 C6 C7 . . 110.49(13)
C5 C6 H6A . . 109.6
C7 C6 H6A . . 109.6
C5 C6 H6B . . 109.6
C7 C6 H6B . . 109.6
H6A C6 H6B . . 108.1
C6 C7 C8 . . 111.94(13)
C6 C7 H7A . . 109.2
C8 C7 H7A . . 109.2
C6 C7 H7B . . 109.2
C8 C7 H7B . . 109.2
H7A C7 H7B . . 107.9
N2 C8 C3 . . 110.00(11)
N2 C8 C7 . . 113.85(13)
C3 C8 C7 . . 109.72(12)
N2 C8 H8 . . 107.7
C3 C8 H8 . . 107.7
C7 C8 H8 . . 107.7
N2 C9 C10 . . 110.88(13)
N2 C9 C1 . 2_566 109.54(12)
C10 C9 C1 . 2_566 111.64(13)
N2 C9 H9 . . 108.2
C10 C9 H9 . . 108.2
C1 C9 H9 2_566 . 108.2
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
O1 C11 C12 . . 113.97(13)
O1 C11 H11A . . 108.8
C12 C11 H11A . . 108.8
O1 C11 H11B . . 108.8
C12 C11 H11B . . 108.8
H11A C11 H11B . . 107.7
C13 C12 C21 . . 119.27(15)
C13 C12 C11 . . 121.36(15)
C21 C12 C11 . . 119.36(14)
C12 C13 C14 . . 121.18(16)
C12 C13 H13 . . 119.4
C14 C13 H13 . . 119.4
C15 C14 C13 . . 120.84(16)
C15 C14 H14 . . 119.6
C13 C14 H14 . . 119.6
C14 C15 C16 . . 120.42(15)
C14 C15 H15 . . 119.8
C16 C15 H15 . . 119.8
C17 C16 C15 . . 121.61(15)
C17 C16 C21 . . 119.41(15)
C15 C16 C21 . . 118.96(15)
C18 C17 C16 . . 121.05(16)
C18 C17 H17 . . 119.5
C16 C17 H17 . . 119.5
C17 C18 C19 . . 119.87(16)
C17 C18 H18 . . 120.1
C19 C18 H18 . . 120.1
C20 C19 C18 . . 120.63(16)
C20 C19 H19 . . 119.7
C18 C19 H19 . . 119.7
C19 C20 C21 . . 121.27(15)
C19 C20 H20 . . 119.4
C21 C20 H20 . . 119.4
C20 C21 C16 . . 117.77(15)
C20 C21 C12 . . 122.93(14)
C16 C21 C12 . . 119.29(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C11 . 1.4159(19)
O1 H1O . 0.852(9)
N1 C2 . 1.4730(19)
N1 C3 . 1.4739(19)
N1 H1N . 0.883(9)
N2 C8 . 1.4712(19)
N2 C9 . 1.4798(19)
N2 H2N . 0.884(9)
C1 C2 . 1.525(2)
C1 C9 2_566 1.529(2)
C1 H1A . 0.9900
C1 H1B . 0.9900
C2 H2A . 0.9900
C2 H2B . 0.9900
C3 C8 . 1.531(2)
C3 C4 . 1.531(2)
C3 H3 . 1.0000
C4 C5 . 1.527(2)
C4 H4A . 0.9900
C4 H4B . 0.9900
C5 C6 . 1.521(2)
C5 H5A . 0.9900
C5 H5B . 0.9900
C6 C7 . 1.523(2)
C6 H6A . 0.9900
C6 H6B . 0.9900
C7 C8 . 1.536(2)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 H8 . 1.0000
C9 C10 . 1.522(2)
C9 C1 2_566 1.529(2)
C9 H9 . 1.0000
C10 H10A . 0.9800
C10 H10B . 0.9800
C10 H10C . 0.9800
C11 C12 . 1.509(2)
C11 H11A . 0.9900
C11 H11B . 0.9900
C12 C13 . 1.370(2)
C12 C21 . 1.432(2)
C13 C14 . 1.408(2)
C13 H13 . 0.9500
C14 C15 . 1.356(2)
C14 H14 . 0.9500
C15 C16 . 1.422(2)
C15 H15 . 0.9500
C16 C17 . 1.416(2)
C16 C21 . 1.423(2)
C17 C18 . 1.366(3)
C17 H17 . 0.9500
C18 C19 . 1.402(2)
C18 H18 . 0.9500
C19 C20 . 1.369(2)
C19 H19 . 0.9500
C20 C21 . 1.419(2)
C20 H20 . 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1o N1 0.850(10) 1.940(10) 2.786(2) 171(2)
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_4
_geom_torsion
C3 N1 C2 C1 . . -172.40(12)
C9 C1 C2 N1 2_566 . 74.70(17)
C2 N1 C3 C8 . . 166.81(12)
C2 N1 C3 C4 . . -71.62(16)
N1 C3 C4 C5 . . -178.15(12)
C8 C3 C4 C5 . . -56.50(16)
C3 C4 C5 C6 . . 55.34(18)
C4 C5 C6 C7 . . -54.34(19)
C5 C6 C7 C8 . . 56.62(17)
C9 N2 C8 C3 . . 174.49(11)
C9 N2 C8 C7 . . -61.91(16)
N1 C3 C8 N2 . . -55.05(15)
C4 C3 C8 N2 . . -177.19(12)
N1 C3 C8 C7 . . 178.97(11)
C4 C3 C8 C7 . . 56.83(16)
C6 C7 C8 N2 . . 178.14(12)
C6 C7 C8 C3 . . -58.10(16)
C8 N2 C9 C10 . . -62.00(16)
C8 N2 C9 C1 . 2_566 174.34(12)
O1 C11 C12 C13 . . 4.5(2)
O1 C11 C12 C21 . . -175.56(13)
C21 C12 C13 C14 . . 0.2(2)
C11 C12 C13 C14 . . -179.85(14)
C12 C13 C14 C15 . . 1.3(2)
C13 C14 C15 C16 . . -1.3(2)
C14 C15 C16 C17 . . -178.88(15)
C14 C15 C16 C21 . . -0.3(2)
C15 C16 C17 C18 . . 177.67(15)
C21 C16 C17 C18 . . -0.9(2)
C16 C17 C18 C19 . . 0.4(2)
C17 C18 C19 C20 . . 0.0(2)
C18 C19 C20 C21 . . 0.2(2)
C19 C20 C21 C16 . . -0.7(2)
C19 C20 C21 C12 . . 179.92(14)
C17 C16 C21 C20 . . 1.0(2)
C15 C16 C21 C20 . . -177.60(14)
C17 C16 C21 C12 . . -179.56(14)
C15 C16 C21 C12 . . 1.8(2)
C13 C12 C21 C20 . . 177.61(14)
C11 C12 C21 C20 . . -2.3(2)
C13 C12 C21 C16 . . -1.8(2)
C11 C12 C21 C16 . . 178.28(13)
