#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239087.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_2239087
loop_
_publ_author_name
'Gayathri, K.'
'Sathya, S.'
'Usha, G.'
'Ramanjaneya Reddy, G.'
'Balasubramanian, S.'
_publ_section_title
;
 5,5,7,12,12,14-Hexamethyl-1,8-bis(4-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o50
_journal_paper_doi               10.1107/S1600536813031164
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C30 H46 N6 O4'
_chemical_formula_moiety         'C30 H46 N6 O4'
_chemical_formula_sum            'C30 H46 N6 O4'
_chemical_formula_weight         554.73
_chemical_name_systematic
5,5,7,12,12,14-Hexamethyl-1,8-bis(4-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane
_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                107.742(2)
_cell_angle_beta                 104.898(2)
_cell_angle_gamma                102.372(2)
_cell_formula_units_Z            1
_cell_length_a                   8.6407(4)
_cell_length_b                   9.1433(3)
_cell_length_c                   11.0008(5)
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      31.120
_cell_measurement_theta_min      0.986
_cell_volume                     758.45(6)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18201
_diffrn_reflns_theta_full        31.12
_diffrn_reflns_theta_max         31.12
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0506
_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)+(0.1167P)²+0.0862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1848
_reflns_number_gt                3340
_reflns_number_total             4819
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vm2199sup1.cif
_cod_data_source_block           I
_cod_database_code               2239087
_cod_database_fobs_code          2239087
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
C C1 0.17573(15) 0.33128(15) 0.19940(12) 0.0405(3) Uani d . 1 1
H H1 0.1959 0.3975 0.2942 0.049 Uiso calc R 1 1
C C2 0.26370(18) 0.93648(14) 0.50435(14) 0.0469(3) Uani d . 1 1
C C3 0.19243(17) 0.89974(15) 0.36661(14) 0.0466(3) Uani d . 1 1
H H3 0.1203 0.9525 0.3346 0.056 Uiso calc R 1 1
C C4 0.23154(16) 0.78245(15) 0.27817(13) 0.0431(3) Uani d . 1 1
H H4 0.1849 0.7554 0.1850 0.052 Uiso calc R 1 1
C C5 0.33941(14) 0.70422(13) 0.32604(12) 0.0384(3) Uani d . 1 1
C C6 0.40708(17) 0.74400(16) 0.46470(13) 0.0469(3) Uani d . 1 1
H H6 0.4791 0.6915 0.4974 0.056 Uiso calc R 1 1
C C7 0.37823(15) 0.57761(15) 0.22457(13) 0.0441(3) Uani d . 1 1
H H7A 0.4292 0.6259 0.1712 0.053 Uiso calc R 1 1
H H7B 0.4584 0.5366 0.2724 0.053 Uiso calc R 1 1
C C8 0.2822(2) 0.2174(2) 0.20329(19) 0.0615(4) Uani d . 1 1
H H8A 0.3998 0.2799 0.2438 0.092 Uiso calc R 1 1
H H8B 0.2596 0.1444 0.1123 0.092 Uiso calc R 1 1
H H8C 0.2537 0.1565 0.2562 0.092 Uiso calc R 1 1
C C9 -0.01195(16) 0.23196(14) 0.13605(14) 0.0427(3) Uani d . 1 1
H H9A -0.0295 0.1501 0.1746 0.051 Uiso calc R 1 1
H H9B -0.0366 0.1755 0.0396 0.051 Uiso calc R 1 1
C C10 0.22706(16) 0.36646(14) -0.00178(12) 0.0395(3) Uani d . 1 1
H H10A 0.1226 0.2776 -0.0545 0.047 Uiso calc R 1 1
H H10B 0.3190 0.3208 0.0056 0.047 Uiso calc R 1 1
C C11 0.24794(16) 0.47711(16) -0.07869(14) 0.0439(3) Uani d . 1 1
H H11A 0.3646 0.5463 -0.0422 0.053 Uiso calc R 1 1
H H11B 0.2231 0.4118 -0.1735 0.053 Uiso calc R 1 1
C C12 0.14282(15) 0.68065(14) -0.15082(13) 0.0403(3) Uani d . 1 1
C C13 0.31661(18) 0.81153(19) -0.08704(18) 0.0604(4) Uani d . 1 1
H H13A 0.4025 0.7614 -0.0944 0.091 Uiso calc R 1 1
H H13B 0.3368 0.8705 0.0072 0.091 Uiso calc R 1 1
H H13C 0.3193 0.8845 -0.1339 0.091 Uiso calc R 1 1
C C14 0.1105(2) 0.5867(2) -0.30121(15) 0.0606(4) Uani d . 1 1
H H14A 0.0017 0.5051 -0.3412 0.091 Uiso calc R 1 1
H H14B 0.1962 0.5363 -0.3088 0.091 Uiso calc R 1 1
H H14C 0.1135 0.6599 -0.3479 0.091 Uiso calc R 1 1
C C15 0.36900(19) 0.86074(17) 0.55532(13) 0.0512(3) Uani d . 1 1
H H15 0.4139 0.8870 0.6485 0.061 Uiso calc R 1 1
N N1 0.2281(2) 1.06532(16) 0.59985(15) 0.0653(4) Uani d . 1 1
N N2 0.22416(11) 0.44428(11) 0.13438(9) 0.0347(2) Uani d . 1 1
N N3 0.13852(12) 0.57798(12) -0.07040(10) 0.0348(2) Uani d . 1 1
O O1 0.1657(2) 1.15487(16) 0.55712(16) 0.0867(4) Uani d . 1 1
O O2 0.2633(3) 1.0778(2) 0.71694(15) 0.1117(6) Uani d . 1 1
H H3A 0.0333(19) 0.5159(18) -0.0954(14) 0.044(4) Uiso 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
N2 C1 C9 . . 112.95(9)
N2 C1 C8 . . 113.69(11)
C9 C1 C8 . . 109.55(11)
N2 C1 H1 . . 106.7
C9 C1 H1 . . 106.7
C8 C1 H1 . . 106.7
C15 C2 C3 . . 122.80(12)
C15 C2 N1 . . 118.71(13)
C3 C2 N1 . . 118.47(14)
C4 C3 C2 . . 117.93(13)
C4 C3 H3 . . 121.0
C2 C3 H3 . . 121.0
C3 C4 C5 . . 120.98(12)
C3 C4 H4 . . 119.5
C5 C4 H4 . . 119.5
C6 C5 C4 . . 119.18(11)
C6 C5 C7 . . 122.20(12)
C4 C5 C7 . . 118.62(11)
C15 C6 C5 . . 120.86(13)
C15 C6 H6 . . 119.6
C5 C6 H6 . . 119.6
N2 C7 C5 . . 110.45(9)
N2 C7 H7A . . 109.6
C5 C7 H7A . . 109.6
N2 C7 H7B . . 109.6
C5 C7 H7B . . 109.6
H7A C7 H7B . . 108.1
C1 C8 H8A . . 109.5
C1 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C1 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C1 C9 C12 . 2_565 118.88(10)
C1 C9 H9A . . 107.6
C12 C9 H9A 2_565 . 107.6
C1 C9 H9B . . 107.6
C12 C9 H9B 2_565 . 107.6
H9A C9 H9B . . 107.0
N2 C10 C11 . . 114.82(10)
N2 C10 H10A . . 108.6
C11 C10 H10A . . 108.6
N2 C10 H10B . . 108.6
C11 C10 H10B . . 108.6
H10A C10 H10B . . 107.5
N3 C11 C10 . . 112.80(10)
N3 C11 H11A . . 109.0
C10 C11 H11A . . 109.0
N3 C11 H11B . . 109.0
C10 C11 H11B . . 109.0
H11A C11 H11B . . 107.8
N3 C12 C9 . 2_565 107.94(9)
N3 C12 C14 . . 113.61(11)
C9 C12 C14 2_565 . 110.55(11)
N3 C12 C13 . . 108.11(11)
C9 C12 C13 2_565 . 106.91(11)
C14 C12 C13 . . 109.47(11)
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
C12 C14 H14A . . 109.5
C12 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C12 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C2 C15 C6 . . 118.25(12)
C2 C15 H15 . . 120.9
C6 C15 H15 . . 120.9
O2 N1 O1 . . 123.36(15)
O2 N1 C2 . . 118.46(16)
O1 N1 C2 . . 118.18(15)
C10 N2 C7 . . 113.41(9)
C10 N2 C1 . . 114.37(9)
C7 N2 C1 . . 111.66(10)
C11 N3 C12 . . 115.96(9)
C11 N3 H3A . . 109.2(10)
C12 N3 H3A . . 108.6(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N2 . 1.4742(15)
C1 C9 . 1.5305(17)
C1 C8 . 1.5328(19)
C1 H1 . 0.9800
C2 C15 . 1.366(2)
C2 C3 . 1.382(2)
C2 N1 . 1.4675(18)
C3 C4 . 1.3781(18)
C3 H3 . 0.9300
C4 C5 . 1.3859(18)
C4 H4 . 0.9300
C5 C6 . 1.3831(17)
C5 C7 . 1.5067(17)
C6 C15 . 1.383(2)
C6 H6 . 0.9300
C7 N2 . 1.4598(14)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C9 C12 2_565 1.5317(18)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 N2 . 1.4588(15)
C10 C11 . 1.5145(17)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 N3 . 1.4559(16)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 N3 . 1.4743(15)
C12 C9 2_565 1.5317(18)
C12 C14 . 1.5318(19)
C12 C13 . 1.5349(18)
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C15 H15 . 0.9300
N1 O2 . 1.208(2)
N1 O1 . 1.214(2)
N3 H3A . 0.883(15)
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
N3 H3A N2 2_565 0.883(17) 2.284(17) 2.9770(15) 135.3(15)
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
C15 C2 C3 C4 . . -0.6(2)
N1 C2 C3 C4 . . 177.77(11)
C2 C3 C4 C5 . . -0.19(19)
C3 C4 C5 C6 . . 0.62(18)
C3 C4 C5 C7 . . -179.70(11)
C4 C5 C6 C15 . . -0.30(19)
C7 C5 C6 C15 . . -179.97(12)
C6 C5 C7 N2 . . 118.14(13)
C4 C5 C7 N2 . . -61.53(15)
N2 C1 C9 C12 . 2_565 -66.10(14)
C8 C1 C9 C12 . 2_565 166.07(12)
N2 C10 C11 N3 . . -45.97(15)
C3 C2 C15 C6 . . 0.9(2)
N1 C2 C15 C6 . . -177.46(12)
C5 C6 C15 C2 . . -0.4(2)
C15 C2 N1 O2 . . -15.0(2)
C3 C2 N1 O2 . . 166.54(16)
C15 C2 N1 O1 . . 164.41(15)
C3 C2 N1 O1 . . -14.0(2)
C11 C10 N2 C7 . . -60.07(13)
C11 C10 N2 C1 . . 170.32(10)
C5 C7 N2 C10 . . 149.14(10)
C5 C7 N2 C1 . . -79.89(13)
C9 C1 N2 C10 . . -71.93(13)
C8 C1 N2 C10 . . 53.70(14)
C9 C1 N2 C7 . . 157.59(10)
C8 C1 N2 C7 . . -76.78(13)
C10 C11 N3 C12 . . -175.81(10)
C9 C12 N3 C11 2_565 . 176.37(10)
C14 C12 N3 C11 . . 53.40(15)
C13 C12 N3 C11 . . -68.32(14)
