# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 182/1435

data_gd792s

_audit_creation_method            SHELXL
_chemical_name_systematic
;
 N-cyclohexyl-N'-(butylaminocarbonyl)squaramide
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C15 H23 N3 O3'
_chemical_formula_weight          293.36
_chemical_melting_point           ?
_chemical_compound_source         ?

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'
 'O'  'O'   0.0106   0.0060
 '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'

_symmetry_cell_setting            ?
_symmetry_space_group_name_H-M    ?

loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                    5.9800(4)
_cell_length_b                    9.5090(5)
_cell_length_c                    14.1543(8)
_cell_angle_alpha                 89.694(6)
_cell_angle_beta                  81.471(5)
_cell_angle_gamma                 87.322(5)
_cell_volume                      795.10(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.225
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              316
_exptl_absorpt_coefficient_mu     0.086
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
 ?
;

_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device        ?
_diffrn_measurement_method        ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             3009
_diffrn_reflns_av_R_equivalents   0.0271
_diffrn_reflns_av_sigmaI/netI     0.0458
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          1.45
_diffrn_reflns_theta_max          24.97
_reflns_number_total              2726
_reflns_number_observed           1673
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics     ?
_computing_publication_material   ?

_refine_special_details
;
 Refinement on F^2^ for ALL reflections except for 3 with very negative F^2^
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F^2^, conventional R-factors R
 are based on F, with F set to zero for negative F^2^. The observed criterion
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme
 'calc w=1/[\s^2^(Fo^2^)+(0.0743P)^2^+0.2345P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     ?
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2723
_refine_ls_number_parameters      282
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1081
_refine_ls_R_factor_obs           0.0510
_refine_ls_wR_factor_all          0.1575
_refine_ls_wR_factor_obs          0.1250
_refine_ls_goodness_of_fit_all    1.070
_refine_ls_goodness_of_fit_obs    1.130
_refine_ls_restrained_S_all       1.078
_refine_ls_restrained_S_obs       1.130
_refine_ls_shift/esd_max          7.463
_refine_ls_shift/esd_mean         0.879

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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
O2 O 1.1109(5) 0.9916(3) 0.8368(2) 0.0657(8) Uani 1 d . .
O3 O 1.1628(4) 1.0531(3) 0.6069(2) 0.0642(8) Uani 1 d . .
O5 O 0.4513(4) 0.7506(3) 0.6646(2) 0.0639(8) Uani 1 d . .
N1 N 0.6539(5) 0.8246(3) 0.8235(2) 0.0478(8) Uani 1 d . .
N2 N 0.7290(5) 0.8858(3) 0.5880(2) 0.0514(8) Uani 1 d . .
N3 N 0.4912(5) 0.7765(4) 0.5039(2) 0.0573(9) Uani 1 d . .
C1 C 0.8014(5) 0.8885(4) 0.7628(2) 0.0421(8) Uani 1 d . .
C2 C 1.0097(6) 0.9649(4) 0.7719(2) 0.0470(9) Uani 1 d . .
C3 C 1.0317(6) 0.9921(4) 0.6668(2) 0.0489(9) Uani 1 d . .
C4 C 0.8330(5) 0.9154(4) 0.6640(2) 0.0436(8) Uani 1 d . .
C5 C 0.5456(6) 0.7997(4) 0.5904(2) 0.0479(9) Uani 1 d . .
C6 C 0.3021(8) 0.6907(7) 0.4916(3) 0.0703(14) Uani 1 d . .
C7 C 0.2970(9) 0.6561(6) 0.3909(3) 0.0692(13) Uani 1 d . .
C8 C 0.0974(11) 0.5711(7) 0.3764(4) 0.089(2) Uani 1 d . .
C9 C 0.0685(15) 0.5364(10) 0.2822(5) 0.136(3) Uani 1 d . .
C10 C 0.6721(6) 0.8110(4) 0.9256(2) 0.0421(8) Uani 1 d . .
C11 C 0.8314(7) 0.6898(4) 0.9440(3) 0.0507(9) Uani 1 d . .
C12 C 0.8493(7) 0.6801(5) 1.0500(3) 0.0576(10) Uani 1 d . .
C13 C 0.6187(7) 0.6661(5) 1.1093(3) 0.0617(11) Uani 1 d . .
C14 C 0.4567(7) 0.7856(5) 1.0889(3) 0.0564(10) Uani 1 d . .
C15 C 0.4406(6) 0.7966(5) 0.9828(3) 0.0493(9) Uani 1 d . .
H1 H 0.5412(77) 0.7890(45) 0.8012(31) 0.078(13) Uiso 1 d . .
H2 H 0.7908(63) 0.9146(38) 0.5297(29) 0.053(11) Uiso 1 d . .
H3 H 0.5641(73) 0.8118(45) 0.4557(32) 0.060(13) Uiso 1 d . .
H61 H 0.3056(59) 0.6054(39) 0.5335(27) 0.102(10) Uiso 1 d . .
H62 H 0.1605(63) 0.7499(36) 0.5188(25) 0.091(10) Uiso 1 d . .
H71 H 0.4436(66) 0.6144(37) 0.3619(26) 0.069(10) Uiso 1 d . .
H72 H 0.3002(58) 0.7415(38) 0.3516(25) 0.074(10) Uiso 1 d . .
H81 H 0.1083(57) 0.4777(37) 0.4195(25) 0.098(10) Uiso 1 d . .
H82 H -0.0579(63) 0.6007(35) 0.4127(25) 0.103(10) Uiso 1 d . .
H91 H -0.0667(60) 0.4735(36) 0.2793(24) 0.103(9) Uiso 1 d . .
H92 H 0.0598(65) 0.6262(39) 0.2464(29) 0.107(11) Uiso 1 d . .
H93 H 0.1993(61) 0.5381(38) 0.2271(27) 0.125(10) Uiso 1 d . .
H10 H 0.7293(53) 0.8943(35) 0.9442(23) 0.046(9) Uiso 1 d . .
H112 H 0.9745(67) 0.7005(37) 0.9082(27) 0.057(11) Uiso 1 d . .
H113 H 0.7715(58) 0.5977(38) 0.9206(25) 0.049(10) Uiso 1 d . .
H121 H 0.9157(64) 0.7617(44) 1.0685(28) 0.066(12) Uiso 1 d . .
H122 H 0.9586(85) 0.6018(53) 1.0642(33) 0.087(16) Uiso 1 d . .
H131 H 0.5494(83) 0.5827(53) 1.0971(34) 0.091(15) Uiso 1 d . .
H132 H 0.6307(63) 0.6640(39) 1.1796(30) 0.076(11) Uiso 1 d . .
H141 H 0.5199(68) 0.8744(44) 1.1122(29) 0.077(12) Uiso 1 d . .
H142 H 0.3051(75) 0.7752(43) 1.1210(30) 0.070(13) Uiso 1 d . .
H151 H 0.3774(62) 0.7135(41) 0.9622(26) 0.045(11) Uiso 1 d . .
H152 H 0.3365(65) 0.8708(41) 0.9696(26) 0.056(11) Uiso 1 d . .

loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
O2 0.067(2) 0.089(2) 0.047(2) 0.0022(13) -0.0205(13) -0.0297(15)
O3 0.058(2) 0.093(2) 0.0440(15) 0.0087(13) -0.0073(12) -0.0360(15)
O5 0.062(2) 0.090(2) 0.0420(15) 0.0082(13) -0.0074(12) -0.0370(15)
N1 0.045(2) 0.063(2) 0.038(2) 0.0060(13) -0.0114(13) -0.0145(15)
N2 0.048(2) 0.074(2) 0.036(2) 0.0066(14) -0.0100(13) -0.026(2)
N3 0.054(2) 0.085(2) 0.036(2) 0.001(2) -0.0073(14) -0.033(2)
C1 0.040(2) 0.049(2) 0.038(2) 0.0003(14) -0.0068(14) -0.005(2)
C2 0.046(2) 0.055(2) 0.042(2) 0.000(2) -0.011(2) -0.009(2)
C3 0.043(2) 0.065(2) 0.041(2) 0.002(2) -0.008(2) -0.015(2)
C4 0.042(2) 0.053(2) 0.037(2) 0.0012(14) -0.0076(14) -0.007(2)
C5 0.043(2) 0.064(2) 0.039(2) 0.001(2) -0.0068(15) -0.015(2)
C6 0.060(3) 0.101(4) 0.054(3) -0.010(3) -0.009(2) -0.039(3)
C7 0.072(3) 0.088(4) 0.052(2) -0.002(2) -0.016(2) -0.029(3)
C8 0.096(4) 0.115(4) 0.063(3) -0.003(3) -0.022(3) -0.052(4)
C9 0.151(6) 0.193(8) 0.076(4) 0.004(5) -0.035(4) -0.098(6)
C10 0.045(2) 0.048(2) 0.035(2) 0.0013(14) -0.0082(14) -0.010(2)
C11 0.048(2) 0.061(3) 0.044(2) -0.005(2) -0.008(2) 0.003(2)
C12 0.059(2) 0.066(3) 0.050(2) 0.001(2) -0.017(2) 0.008(2)
C13 0.074(3) 0.068(3) 0.045(2) 0.014(2) -0.015(2) -0.012(2)
C14 0.044(2) 0.081(3) 0.042(2) 0.004(2) -0.001(2) -0.008(2)
C15 0.040(2) 0.064(3) 0.045(2) 0.005(2) -0.009(2) -0.003(2)

_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O2 C2 1.207(4) . ?
O3 C3 1.229(4) . ?
O5 C5 1.218(4) . ?
N1 C1 1.306(4) . ?
N1 C10 1.469(4) . ?
N2 C4 1.356(4) . ?
N2 C5 1.395(4) . ?
N3 C5 1.335(4) . ?
N3 C6 1.456(5) . ?
C1 C4 1.407(4) . ?
C1 C2 1.493(5) . ?
C2 C3 1.496(5) . ?
C3 C4 1.428(5) . ?
C6 C7 1.470(6) . ?
C7 C8 1.511(6) . ?
C8 C9 1.412(7) . ?
C10 C11 1.508(5) . ?
C10 C15 1.508(5) . ?
C11 C12 1.522(5) . ?
C12 C13 1.515(6) . ?
C13 C14 1.513(6) . ?
C14 C15 1.523(5) . ?

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
C1 N1 C10 123.0(3) . . ?
C4 N2 C5 125.2(3) . . ?
C5 N3 C6 121.1(3) . . ?
N1 C1 C4 136.2(3) . . ?
N1 C1 C2 133.8(3) . . ?
C4 C1 C2 89.9(3) . . ?
O2 C2 C1 135.1(3) . . ?
O2 C2 C3 137.4(3) . . ?
C1 C2 C3 87.5(3) . . ?
O3 C3 C4 134.6(3) . . ?
O3 C3 C2 136.4(3) . . ?
C4 C3 C2 89.0(3) . . ?
N2 C4 C1 137.4(3) . . ?
N2 C4 C3 129.0(3) . . ?
C1 C4 C3 93.6(3) . . ?
O5 C5 N3 125.0(3) . . ?
O5 C5 N2 122.1(3) . . ?
N3 C5 N2 112.8(3) . . ?
N3 C6 C7 112.4(4) . . ?
C6 C7 C8 113.2(4) . . ?
C9 C8 C7 118.5(5) . . ?
N1 C10 C11 111.7(3) . . ?
N1 C10 C15 110.0(3) . . ?
C11 C10 C15 111.3(3) . . ?
C10 C11 C12 110.3(3) . . ?
C13 C12 C11 111.2(3) . . ?
C12 C13 C14 110.9(3) . . ?
C15 C14 C13 111.5(4) . . ?
C10 C15 C14 110.5(3) . . ?

_refine_diff_density_max    0.315
_refine_diff_density_min   -0.179
_refine_diff_density_rms    0.049