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The asymmetric unit of the title compound, C10H14N2O, contains two mol­ecules having similar conformation. The mol­ecules are connected via N—H...O hydrogen bonds, forming a three-dimensional network in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040244/ob2066sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040244/ob2066Isup2.hkl
Contains datablock I

CCDC reference: 628020

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.047
  • wR factor = 0.132
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT353_ALERT_3_C Long N-H Bond (0.87A) N1A - H2NA ... 1.01 Ang. PLAT353_ALERT_3_C Long N-H Bond (0.87A) N1B - H2NB ... 1.01 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 16 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C10 H14 N2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 and local procedures.

4-morpholinoaniline top
Crystal data top
C10H14N2OF(000) = 384
Mr = 178.23Dx = 1.296 Mg m3
Triclinic, P1Melting point = 401–405 K
a = 9.7252 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.4534 (2) ÅCell parameters from 4163 reflections
c = 10.6002 (3) Åθ = 1.0–27.5°
α = 100.4721 (9)°µ = 0.09 mm1
β = 97.0821 (9)°T = 90 K
γ = 117.4777 (10)°Block, orange–brown
V = 913.25 (4) Å30.25 × 0.20 × 0.15 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2903 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
Detector resolution: 18 pixels mm-1h = 1212
ω scans at fixed χ = 55°k = 1313
8318 measured reflectionsl = 1313
4199 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0736P)2 + 0.0298P]
where P = (Fo2 + 2Fc2)/3
4199 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.71140 (12)0.12164 (11)0.06223 (9)0.0244 (3)
N1A0.79358 (15)0.11241 (14)0.88549 (11)0.0261 (3)
H1NA0.90130.17920.94390.039*
H2NA0.74710.01890.91640.039*
C1A0.78015 (16)0.07856 (16)0.74870 (13)0.0197 (3)
N2A0.73325 (13)0.00154 (13)0.33298 (11)0.0183 (3)
C2A0.65058 (17)0.04987 (16)0.66286 (14)0.0212 (3)
H2A0.57180.11900.69780.025*
C3A0.63398 (16)0.07928 (16)0.52688 (14)0.0208 (3)
H3A0.54450.16830.47050.025*
C4A0.74644 (16)0.01975 (15)0.47219 (13)0.0171 (3)
C5A0.87650 (16)0.14855 (16)0.55850 (13)0.0193 (3)
H5A0.95530.21760.52360.023*
C6A0.89339 (16)0.17805 (15)0.69399 (13)0.0198 (3)
H6A0.98300.26700.75030.024*
C7A0.86747 (16)0.00889 (17)0.28982 (13)0.0211 (3)
H7A10.86390.10320.29780.025*
H7A20.96930.07600.34690.025*
C8A0.85899 (17)0.00234 (17)0.14850 (14)0.0248 (3)
H8A10.86960.09500.14220.030*
H8A20.94910.00910.11980.030*
C9A0.57831 (17)0.11940 (17)0.10637 (14)0.0240 (3)
H9A10.47790.20570.04880.029*
H9A20.57820.02660.09820.029*
C10A0.58409 (16)0.12652 (16)0.24784 (13)0.0208 (3)
H10A0.49270.12160.27550.025*
H10B0.57650.22240.25570.025*
O1B0.72835 (11)0.55597 (11)0.13716 (9)0.0223 (3)
N1B0.83270 (14)0.34429 (14)0.96100 (11)0.0233 (3)
H1NB0.81180.42331.00560.035*
H2NB0.79120.27670.99810.035*
C1B0.79408 (16)0.39632 (16)0.82184 (13)0.0192 (3)
N2B0.69172 (13)0.54862 (12)0.40194 (11)0.0179 (3)
C2B0.76889 (16)0.31280 (15)0.74291 (13)0.0191 (3)
H2B0.77350.22160.78350.023*
C3B0.73709 (16)0.35979 (15)0.60614 (13)0.0189 (3)
H3B0.72090.30000.55490.023*
C4B0.72853 (15)0.49309 (15)0.54295 (13)0.0169 (3)
C5B0.75331 (16)0.57738 (15)0.62212 (13)0.0187 (3)
H5B0.74770.66900.58150.022*
C6B0.78590 (16)0.53012 (16)0.75867 (13)0.0198 (3)
H6B0.80290.58940.81000.024*
C7B0.81091 (17)0.58146 (16)0.35347 (13)0.0198 (3)
H7B10.82470.65200.39750.024*
H7B20.91490.48780.37610.024*
C8B0.75948 (17)0.64932 (16)0.20534 (14)0.0224 (3)
H8B10.84440.66450.17480.027*
H8B20.66190.74850.18390.027*
C9B0.60625 (17)0.53376 (16)0.18173 (13)0.0220 (3)
H9B10.50770.63180.16270.026*
H9B20.58240.47140.13290.026*
C10B0.65590 (16)0.45806 (15)0.32828 (13)0.0191 (3)
H10C0.75140.35780.34730.023*
H10D0.56880.44480.35630.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0238 (6)0.0243 (6)0.0186 (5)0.0088 (5)0.0034 (4)0.0012 (4)
N1A0.0279 (7)0.0321 (8)0.0176 (6)0.0142 (6)0.0051 (5)0.0066 (5)
C1A0.0220 (7)0.0239 (8)0.0184 (7)0.0150 (6)0.0058 (6)0.0067 (6)
N2A0.0170 (6)0.0203 (6)0.0151 (6)0.0084 (5)0.0014 (5)0.0029 (5)
C2A0.0200 (7)0.0221 (8)0.0234 (8)0.0103 (6)0.0084 (6)0.0083 (6)
C3A0.0180 (7)0.0181 (7)0.0242 (8)0.0081 (6)0.0041 (6)0.0038 (6)
C4A0.0200 (7)0.0194 (7)0.0164 (7)0.0134 (6)0.0040 (6)0.0053 (6)
C5A0.0190 (7)0.0191 (7)0.0216 (8)0.0102 (6)0.0052 (6)0.0071 (6)
C6A0.0190 (7)0.0197 (7)0.0199 (7)0.0109 (6)0.0008 (6)0.0022 (6)
C7A0.0181 (7)0.0235 (8)0.0196 (7)0.0091 (6)0.0040 (6)0.0049 (6)
C8A0.0221 (8)0.0244 (8)0.0218 (8)0.0075 (6)0.0046 (6)0.0038 (6)
C9A0.0222 (8)0.0247 (8)0.0214 (8)0.0115 (6)0.0003 (6)0.0010 (6)
C10A0.0182 (7)0.0198 (8)0.0206 (8)0.0083 (6)0.0016 (6)0.0022 (6)
O1B0.0243 (5)0.0253 (6)0.0195 (5)0.0130 (5)0.0068 (4)0.0080 (4)
N1B0.0271 (7)0.0234 (7)0.0158 (6)0.0108 (6)0.0037 (5)0.0032 (5)
C1B0.0137 (7)0.0223 (8)0.0186 (7)0.0067 (6)0.0040 (6)0.0047 (6)
N2B0.0189 (6)0.0182 (6)0.0168 (6)0.0096 (5)0.0041 (5)0.0042 (5)
C2B0.0181 (7)0.0155 (7)0.0199 (7)0.0067 (6)0.0035 (6)0.0019 (6)
C3B0.0165 (7)0.0176 (7)0.0219 (8)0.0074 (6)0.0046 (6)0.0064 (6)
C4B0.0128 (7)0.0175 (7)0.0169 (7)0.0048 (6)0.0036 (5)0.0042 (6)
C5B0.0165 (7)0.0176 (7)0.0213 (7)0.0083 (6)0.0040 (6)0.0045 (6)
C6B0.0161 (7)0.0200 (7)0.0226 (8)0.0075 (6)0.0044 (6)0.0084 (6)
C7B0.0204 (7)0.0204 (7)0.0194 (7)0.0112 (6)0.0045 (6)0.0043 (6)
C8B0.0241 (8)0.0213 (8)0.0223 (8)0.0120 (6)0.0052 (6)0.0054 (6)
C9B0.0207 (7)0.0253 (8)0.0204 (8)0.0119 (6)0.0044 (6)0.0058 (6)
C10B0.0178 (7)0.0182 (7)0.0202 (7)0.0081 (6)0.0035 (6)0.0055 (6)
Geometric parameters (Å, º) top
O1A—C8A1.4358 (16)O1B—C9B1.4282 (16)
O1A—C9A1.4380 (17)O1B—C8B1.4287 (16)
N1A—C1A1.4032 (17)N1B—C1B1.4128 (17)
N1A—H1NA0.9882N1B—H1NB0.9785
N1A—H2NA1.0063N1B—H2NB1.0089
C1A—C2A1.3893 (19)C1B—C2B1.3909 (19)
C1A—C6A1.3967 (19)C1B—C6B1.398 (2)
N2A—C4A1.4322 (16)N2B—C4B1.4353 (16)
N2A—C10A1.4578 (17)N2B—C10B1.4606 (17)
N2A—C7A1.4649 (18)N2B—C7B1.4749 (17)
C2A—C3A1.3907 (19)C2B—C3B1.3890 (18)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C4A1.3905 (19)C3B—C4B1.3918 (19)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.3947 (19)C4B—C5B1.3977 (18)
C5A—C6A1.3853 (18)C5B—C6B1.3864 (18)
C5A—H5A0.9500C5B—H5B0.9500
C6A—H6A0.9500C6B—H6B0.9500
C7A—C8A1.5058 (19)C7B—C8B1.5142 (19)
C7A—H7A10.9900C7B—H7B10.9900
C7A—H7A20.9900C7B—H7B20.9900
C8A—H8A10.9900C8B—H8B10.9900
C8A—H8A20.9900C8B—H8B20.9900
C9A—C10A1.5103 (19)C9B—C10B1.5127 (19)
C9A—H9A10.9900C9B—H9B10.9900
C9A—H9A20.9900C9B—H9B20.9900
C10A—H10A0.9900C10B—H10C0.9900
C10A—H10B0.9900C10B—H10D0.9900
C8A—O1A—C9A110.36 (10)C9B—O1B—C8B109.17 (10)
C1A—N1A—H1NA117.9C1B—N1B—H1NB113.7
C1A—N1A—H2NA111.4C1B—N1B—H2NB115.7
H1NA—N1A—H2NA106.0H1NB—N1B—H2NB112.1
C2A—C1A—C6A117.82 (12)C2B—C1B—C6B117.64 (12)
C2A—C1A—N1A121.55 (12)C2B—C1B—N1B120.90 (13)
C6A—C1A—N1A120.54 (13)C6B—C1B—N1B121.41 (12)
C4A—N2A—C10A116.06 (11)C4B—N2B—C10B114.86 (11)
C4A—N2A—C7A113.77 (10)C4B—N2B—C7B113.66 (10)
C10A—N2A—C7A109.21 (11)C10B—N2B—C7B110.65 (10)
C1A—C2A—C3A121.32 (13)C3B—C2B—C1B121.47 (13)
C1A—C2A—H2A119.3C3B—C2B—H2B119.3
C3A—C2A—H2A119.3C1B—C2B—H2B119.3
C4A—C3A—C2A120.96 (13)C2B—C3B—C4B121.02 (12)
C4A—C3A—H3A119.5C2B—C3B—H3B119.5
C2A—C3A—H3A119.5C4B—C3B—H3B119.5
C3A—C4A—C5A117.65 (12)C3B—C4B—C5B117.57 (12)
C3A—C4A—N2A123.61 (12)C3B—C4B—N2B123.19 (12)
C5A—C4A—N2A118.71 (12)C5B—C4B—N2B119.22 (12)
C6A—C5A—C4A121.51 (13)C6B—C5B—C4B121.43 (13)
C6A—C5A—H5A119.2C6B—C5B—H5B119.3
C4A—C5A—H5A119.2C4B—C5B—H5B119.3
C5A—C6A—C1A120.75 (13)C5B—C6B—C1B120.86 (13)
C5A—C6A—H6A119.6C5B—C6B—H6B119.6
C1A—C6A—H6A119.6C1B—C6B—H6B119.6
N2A—C7A—C8A109.86 (11)N2B—C7B—C8B110.97 (11)
N2A—C7A—H7A1109.7N2B—C7B—H7B1109.4
C8A—C7A—H7A1109.7C8B—C7B—H7B1109.4
N2A—C7A—H7A2109.7N2B—C7B—H7B2109.4
C8A—C7A—H7A2109.7C8B—C7B—H7B2109.4
H7A1—C7A—H7A2108.2H7B1—C7B—H7B2108.0
O1A—C8A—C7A111.66 (11)O1B—C8B—C7B111.77 (11)
O1A—C8A—H8A1109.3O1B—C8B—H8B1109.3
C7A—C8A—H8A1109.3C7B—C8B—H8B1109.3
O1A—C8A—H8A2109.3O1B—C8B—H8B2109.3
C7A—C8A—H8A2109.3C7B—C8B—H8B2109.3
H8A1—C8A—H8A2107.9H8B1—C8B—H8B2107.9
O1A—C9A—C10A112.13 (11)O1B—C9B—C10B111.50 (11)
O1A—C9A—H9A1109.2O1B—C9B—H9B1109.3
C10A—C9A—H9A1109.2C10B—C9B—H9B1109.3
O1A—C9A—H9A2109.2O1B—C9B—H9B2109.3
C10A—C9A—H9A2109.2C10B—C9B—H9B2109.3
H9A1—C9A—H9A2107.9H9B1—C9B—H9B2108.0
N2A—C10A—C9A109.51 (11)N2B—C10B—C9B110.05 (11)
N2A—C10A—H10A109.8N2B—C10B—H10C109.7
C9A—C10A—H10A109.8C9B—C10B—H10C109.7
N2A—C10A—H10B109.8N2B—C10B—H10D109.7
C9A—C10A—H10B109.8C9B—C10B—H10D109.7
H10A—C10A—H10B108.2H10C—C10B—H10D108.2
C6A—C1A—C2A—C3A0.3 (2)C6B—C1B—C2B—C3B0.2 (2)
N1A—C1A—C2A—C3A176.87 (12)N1B—C1B—C2B—C3B177.41 (12)
C1A—C2A—C3A—C4A0.4 (2)C1B—C2B—C3B—C4B0.3 (2)
C2A—C3A—C4A—C5A0.4 (2)C2B—C3B—C4B—C5B0.10 (19)
C2A—C3A—C4A—N2A177.74 (12)C2B—C3B—C4B—N2B178.23 (12)
C10A—N2A—C4A—C3A6.67 (19)C10B—N2B—C4B—C3B2.84 (18)
C7A—N2A—C4A—C3A121.32 (15)C7B—N2B—C4B—C3B126.03 (14)
C10A—N2A—C4A—C5A171.51 (12)C10B—N2B—C4B—C5B175.47 (12)
C7A—N2A—C4A—C5A60.50 (16)C7B—N2B—C4B—C5B55.67 (16)
C3A—C4A—C5A—C6A0.4 (2)C3B—C4B—C5B—C6B0.25 (19)
N2A—C4A—C5A—C6A177.89 (12)N2B—C4B—C5B—C6B178.65 (11)
C4A—C5A—C6A—C1A0.3 (2)C4B—C5B—C6B—C1B0.4 (2)
C2A—C1A—C6A—C5A0.2 (2)C2B—C1B—C6B—C5B0.2 (2)
N1A—C1A—C6A—C5A176.85 (12)N1B—C1B—C6B—C5B177.75 (11)
C4A—N2A—C7A—C8A169.50 (11)C4B—N2B—C7B—C8B176.15 (11)
C10A—N2A—C7A—C8A59.07 (15)C10B—N2B—C7B—C8B52.88 (15)
C9A—O1A—C8A—C7A55.73 (15)C9B—O1B—C8B—C7B58.74 (14)
N2A—C7A—C8A—O1A58.04 (16)N2B—C7B—C8B—O1B55.55 (15)
C8A—O1A—C9A—C10A55.71 (15)C8B—O1B—C9B—C10B60.54 (14)
C4A—N2A—C10A—C9A171.22 (11)C4B—N2B—C10B—C9B175.46 (10)
C7A—N2A—C10A—C9A58.58 (14)C7B—N2B—C10B—C9B54.19 (14)
O1A—C9A—C10A—N2A57.69 (15)O1B—C9B—C10B—N2B58.95 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···N1Bi0.992.303.2728 (17)168
N1A—H2NA···O1Aii1.012.273.2197 (15)157
N1B—H1NB···O1Bii0.982.113.0513 (15)160
N1B—H2NB···O1Aii1.012.143.1461 (16)174
Symmetry codes: (i) x+2, y, z+2; (ii) x, y, z+1.
 

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