#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:27:48 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180340 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/09/7200921.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_7200921
loop_
_publ_author_name
'Jacobs, Tia'
'Lloyd, Gareth O.'
'Bredenkamp, Martin W.'
'Barbour, Leonard J.'
_publ_section_title
;
 Breaking the trigonal host packing motif of Dianin's compound
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1545
_journal_paper_doi               10.1039/b900954j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C18 H20 O2, C5 H11 N1'
_chemical_formula_sum            'C23 H31 N O2'
_chemical_formula_weight         353.49
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.800(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4360(18)
_cell_length_b                   12.9411(15)
_cell_length_c                   10.3343(12)
_cell_measurement_reflns_used    5064
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.57
_cell_volume                     2027.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
X-Seed (Barbour, 2001; Atwood & Barbour, 2003)
;
_computing_publication_material
;
X-Seed (Atwood & Barbour, 2003; Barbour, 2001)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12574
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0477
_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)+(0.0708P)²+0.0399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                3517
_reflns_number_total             4690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b900954j.txt
_cod_data_source_block           c:\tia\work\paperw~1\dianin~2\dianin~2\xx
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7200921
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_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
O1 O 0.82948(6) -0.09467(6) 0.40875(9) 0.0228(2) Uani 1 1 d . . .
N1 N 0.57006(8) 0.55249(9) 0.35848(12) 0.0256(3) Uani 1 1 d . . .
C1 C 0.81063(9) -0.00549(10) 0.32117(13) 0.0223(3) Uani 1 1 d . . .
H1 H 0.5253(10) 0.5842(12) 0.3851(16) 0.035(4) Uiso 1 1 d . . .
H2 H 0.5785(12) 0.4488(15) 0.4526(18) 0.059(6) Uiso 1 1 d . . .
O2 O 0.57755(6) 0.38866(7) 0.51188(10) 0.0263(2) Uani 1 1 d . . .
C2 C 0.87378(8) 0.08135(10) 0.37354(13) 0.0204(3) Uani 1 1 d . . .
H2A H 0.8609 0.1413 0.3136 0.024 Uiso 1 1 calc R . .
H2B H 0.9346 0.0583 0.3711 0.024 Uiso 1 1 calc R . .
C3 C 0.87029(8) 0.11730(9) 0.51466(13) 0.0181(3) Uani 1 1 d . . .
C4 C 0.86851(8) 0.02037(10) 0.59851(13) 0.0183(3) Uani 1 1 d . . .
C5 C 0.89045(9) 0.02371(11) 0.73607(14) 0.0258(3) Uani 1 1 d . . .
H5 H 0.9062 0.0882 0.7777 0.031 Uiso 1 1 calc R . .
C6 C 0.89015(9) -0.06337(12) 0.81385(14) 0.0315(4) Uani 1 1 d . . .
H6 H 0.9043 -0.0580 0.9071 0.038 Uiso 1 1 calc R . .
C7 C 0.86912(9) -0.15819(12) 0.75449(15) 0.0314(4) Uani 1 1 d . . .
H7 H 0.8690 -0.2186 0.8067 0.038 Uiso 1 1 calc R . .
C8 C 0.84836(9) -0.16452(10) 0.61947(15) 0.0264(3) Uani 1 1 d . . .
H8 H 0.8342 -0.2297 0.5787 0.032 Uiso 1 1 calc R . .
C9 C 0.84788(8) -0.07641(10) 0.54158(13) 0.0201(3) Uani 1 1 d . . .
C10 C 0.79066(8) 0.18851(9) 0.51711(12) 0.0166(3) Uani 1 1 d . . .
C11 C 0.72756(8) 0.17148(10) 0.59466(13) 0.0181(3) Uani 1 1 d . . .
H11 H 0.7328 0.1124 0.6501 0.022 Uiso 1 1 calc R . .
C12 C 0.65723(8) 0.23841(10) 0.59329(13) 0.0200(3) Uani 1 1 d . . .
H12 H 0.6154 0.2248 0.6479 0.024 Uiso 1 1 calc R . .
C13 C 0.64749(8) 0.32497(9) 0.51280(13) 0.0188(3) Uani 1 1 d . . .
C14 C 0.71073(9) 0.34416(10) 0.43596(13) 0.0208(3) Uani 1 1 d . . .
H14 H 0.7059 0.4037 0.3813 0.025 Uiso 1 1 calc R . .
C15 C 0.78058(8) 0.27686(10) 0.43883(13) 0.0206(3) Uani 1 1 d . . .
H15 H 0.8231 0.2913 0.3857 0.025 Uiso 1 1 calc R . .
C16 C 0.82889(10) -0.04340(11) 0.18977(14) 0.0326(4) Uani 1 1 d . . .
H16A H 0.7878 -0.0993 0.1568 0.049 Uiso 1 1 calc R . .
H16B H 0.8896 -0.0691 0.2014 0.049 Uiso 1 1 calc R . .
H16C H 0.8210 0.0137 0.1264 0.049 Uiso 1 1 calc R . .
C17 C 0.71314(9) 0.02014(11) 0.31035(14) 0.0272(3) Uani 1 1 d . . .
H17A H 0.6775 -0.0402 0.2768 0.041 Uiso 1 1 calc R . .
H17B H 0.6977 0.0784 0.2498 0.041 Uiso 1 1 calc R . .
H17C H 0.7016 0.0387 0.3975 0.041 Uiso 1 1 calc R . .
C18 C 0.95442(8) 0.18061(10) 0.56577(15) 0.0256(3) Uani 1 1 d . . .
H18A H 0.9550 0.2423 0.5109 0.038 Uiso 1 1 calc R . .
H18B H 1.0065 0.1383 0.5617 0.038 Uiso 1 1 calc R . .
H18C H 0.9552 0.2015 0.6571 0.038 Uiso 1 1 calc R . .
C19 C 0.64433(9) 0.62466(11) 0.37613(16) 0.0326(4) Uani 1 1 d . . .
H19A H 0.6955 0.5904 0.3493 0.039 Uiso 1 1 calc R . .
H19B H 0.6611 0.6425 0.4707 0.039 Uiso 1 1 calc R . .
C20 C 0.62336(11) 0.72309(12) 0.2969(2) 0.0468(5) Uani 1 1 d . . .
H20A H 0.5773 0.7623 0.3310 0.056 Uiso 1 1 calc R . .
H20B H 0.6769 0.7668 0.3070 0.056 Uiso 1 1 calc R . .
C21 C 0.59150(12) 0.69886(15) 0.15324(19) 0.0540(5) Uani 1 1 d . . .
H21A H 0.6407 0.6697 0.1158 0.065 Uiso 1 1 calc R . .
H21B H 0.5719 0.7634 0.1051 0.065 Uiso 1 1 calc R . .
C22 C 0.51576(12) 0.62243(14) 0.13482(16) 0.0461(5) Uani 1 1 d . . .
H22A H 0.4633 0.6556 0.1593 0.055 Uiso 1 1 calc R . .
H22B H 0.5005 0.6020 0.0410 0.055 Uiso 1 1 calc R . .
C23 C 0.54008(10) 0.52720(12) 0.21888(16) 0.0350(4) Uani 1 1 d . . .
H23A H 0.4881 0.4811 0.2099 0.042 Uiso 1 1 calc R . .
H23B H 0.5875 0.4893 0.1863 0.042 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 117.66(9) . . ?
C19 N1 C23 111.12(12) . . ?
C19 N1 H1 107.6(10) . . ?
C23 N1 H1 106.6(10) . . ?
O1 C1 C16 104.46(10) . . ?
O1 C1 C2 108.87(10) . . ?
C16 C1 C2 110.07(12) . . ?
O1 C1 C17 107.24(11) . . ?
C16 C1 C17 110.52(11) . . ?
C2 C1 C17 115.08(11) . . ?
C13 O2 H2 112.2(10) . . ?
C1 C2 C3 115.24(11) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C10 112.51(10) . . ?
C4 C3 C2 107.24(10) . . ?
C10 C3 C2 111.45(10) . . ?
C4 C3 C18 110.20(10) . . ?
C10 C3 C18 107.44(10) . . ?
C2 C3 C18 107.92(10) . . ?
C9 C4 C5 116.68(12) . . ?
C9 C4 C3 121.66(11) . . ?
C5 C4 C3 121.62(12) . . ?
C6 C5 C4 122.56(14) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C7 C6 C5 119.38(14) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C6 119.59(13) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.81(13) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
O1 C9 C4 124.46(11) . . ?
O1 C9 C8 114.53(12) . . ?
C4 C9 C8 120.96(12) . . ?
C11 C10 C15 116.82(11) . . ?
C11 C10 C3 124.20(11) . . ?
C15 C10 C3 118.97(11) . . ?
C12 C11 C10 121.80(12) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C13 C12 C11 120.49(12) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O2 C13 C12 119.45(12) . . ?
O2 C13 C14 122.01(11) . . ?
C12 C13 C14 118.54(11) . . ?
C15 C14 C13 120.22(12) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 122.12(12) . . ?
C14 C15 H15 118.9 . . ?
C10 C15 H15 118.9 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 112.70(12) . . ?
N1 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N1 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 110.75(14) . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 C22 111.17(14) . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C23 C22 C21 110.89(13) . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.0 . . ?
N1 C23 C22 112.41(12) . . ?
N1 C23 H23A 109.1 . . ?
C22 C23 H23A 109.1 . . ?
N1 C23 H23B 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?
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
O1 C9 1.3692(16) . ?
O1 C1 1.4619(15) . ?
N1 C19 1.4635(19) . ?
N1 C23 1.4671(19) . ?
N1 H1 0.891(16) . ?
C1 C16 1.5191(19) . ?
C1 C2 1.5193(18) . ?
C1 C17 1.5245(18) . ?
O2 C13 1.3568(15) . ?
O2 H2 0.992(19) . ?
C2 C3 1.5413(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5277(17) . ?
C3 C10 1.5402(16) . ?
C3 C18 1.5426(17) . ?
C4 C9 1.3949(18) . ?
C4 C5 1.3989(18) . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3949(18) . ?
C8 H8 0.9500 . ?
C10 C11 1.3899(17) . ?
C10 C15 1.3923(17) . ?
C11 C12 1.3869(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3865(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3913(18) . ?
C14 C15 1.3820(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.516(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.507(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.516(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.514(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
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
_geom_hbond_site_symmetry_A
O2 H2 N1 0.992(19) 1.65(2) 2.6368(15) 173.9(16) .
N1 H1 O2 0.891(16) 2.100(16) 2.9513(15) 159.7(14) 3_666
C18 H18B O1 0.98 2.56 3.4792(16) 157.0 3_756
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C16 158.44(11) . . . . ?
C9 O1 C1 C2 40.88(14) . . . . ?
C9 O1 C1 C17 -84.23(12) . . . . ?
O1 C1 C2 C3 -58.50(14) . . . . ?
C16 C1 C2 C3 -172.44(11) . . . . ?
C17 C1 C2 C3 61.88(15) . . . . ?
C1 C2 C3 C4 45.07(13) . . . . ?
C1 C2 C3 C10 -78.47(13) . . . . ?
C1 C2 C3 C18 163.78(10) . . . . ?
C10 C3 C4 C9 106.51(13) . . . . ?
C2 C3 C4 C9 -16.39(15) . . . . ?
C18 C3 C4 C9 -133.61(12) . . . . ?
C10 C3 C4 C5 -75.72(15) . . . . ?
C2 C3 C4 C5 161.39(11) . . . . ?
C18 C3 C4 C5 44.16(15) . . . . ?
C9 C4 C5 C6 -1.45(19) . . . . ?
C3 C4 C5 C6 -179.32(12) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C1 O1 C9 C4 -14.43(17) . . . . ?
C1 O1 C9 C8 168.20(11) . . . . ?
C5 C4 C9 O1 -176.44(11) . . . . ?
C3 C4 C9 O1 1.44(18) . . . . ?
C5 C4 C9 C8 0.77(18) . . . . ?
C3 C4 C9 C8 178.64(11) . . . . ?
C7 C8 C9 O1 177.52(11) . . . . ?
C7 C8 C9 C4 0.05(19) . . . . ?
C4 C3 C10 C11 4.79(17) . . . . ?
C2 C3 C10 C11 125.29(13) . . . . ?
C18 C3 C10 C11 -116.68(13) . . . . ?
C4 C3 C10 C15 -176.17(11) . . . . ?
C2 C3 C10 C15 -55.67(15) . . . . ?
C18 C3 C10 C15 62.36(15) . . . . ?
C15 C10 C11 C12 0.75(18) . . . . ?
C3 C10 C11 C12 179.80(11) . . . . ?
C10 C11 C12 C13 0.41(19) . . . . ?
C11 C12 C13 O2 179.19(11) . . . . ?
C11 C12 C13 C14 -1.37(19) . . . . ?
O2 C13 C14 C15 -179.42(12) . . . . ?
C12 C13 C14 C15 1.15(19) . . . . ?
C13 C14 C15 C10 0.0(2) . . . . ?
C11 C10 C15 C14 -0.97(19) . . . . ?
C3 C10 C15 C14 179.92(12) . . . . ?
C23 N1 C19 C20 56.21(17) . . . . ?
N1 C19 C20 C21 -54.93(18) . . . . ?
C19 C20 C21 C22 52.84(18) . . . . ?
C20 C21 C22 C23 -52.96(19) . . . . ?
C19 N1 C23 C22 -56.09(16) . . . . ?
C21 C22 C23 N1 54.73(19) . . . . ?
