Ortho­rhom­bic polymorph of 1,2-bis­(2-amino­phen­oxy)ethane

Yıldırım, S.Ö.; Akkurt, M.; Özpozan, T.; Heinemann, F.W.

doi:10.1107/S1600536806053657

Orthorhombic polymorph of 1,2-bis(2-aminophenoxy)ethane

S. Ö. Yıldırım, M. Akkurt, T. Özpozan and F. W. Heinemann

The orthorhombic polymorph of the title compound, C₁₄H₁₆N₂O₂, is devoid of crystallographically imposed molecular symmetry. The crystal structure is stabilized by N—H

O hydrogen-bonding interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053657/tk2118sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053657/tk2118Isup2.hkl Contains datablock I

CCDC reference: 634066

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.033
wR factor = 0.084
Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT115_ALERT_5_B ADDSYM Detects Noncrystallographic Inversion ...        100 PerFi
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1B    ..  H2B     ..       2.04 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT128_ALERT_4_C Non-standard setting of Space group Pna21   ....    Pbn21

Alert level G
ABSTY01_ALERT_1_G  Extra text has been found in the _exptl_absorpt_correction_type
            field, which should be only a single keyword. A literature
            citation should be included in the _exptl_absorpt_process_details
            field.
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.50
           From the CIF: _reflns_number_total               1594
           Count of symmetry unique reflns         1649
           Completeness (_total/calc)             96.66%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: SADABS (Sheldrick, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,2-bis(2-aminophenoxy)ethane top

Crystal data top

C₁₄H₁₆N₂O₂	F(000) = 520
M_r = 244.29	D_x = 1.273 Mg m⁻³
Orthorhombic, Pbn2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ab	Cell parameters from 97 reflections
a = 7.0644 (6) Å	θ = 14–40°
b = 7.5770 (7) Å	µ = 0.09 mm⁻¹
c = 23.8053 (10) Å	T = 100 K
V = 1274.23 (17) Å³	Prism, colourless
Z = 4	0.33 × 0.30 × 0.28 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer	1594 independent reflections
Radiation source: fine-focus sealed tube	1530 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 9 pixels mm^-1	θ_max = 28.5°, θ_min = 3.4°
ω scans	h = −9→9
Absorption correction: gaussian integration (Coppens, 1970)	k = −10→10
T_min = 0.972, T_max = 0.976	l = −31→31
13155 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0554P)² + 0.2427P] where P = (F_o² + 2F_c²)/3
1594 reflections	(Δ/σ)_max < 0.001
164 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Special details top

Experimental. IR (cm^-1): 3445 (aromatic NH₂), 3059 (aromatic C—H), 2884 (aliphatic C—H), 1275 (C—N), 1504 (aromatic C═C). ¹H NMR: d 4.0 (s, CH₂—O),4.1–3.4 (s, Ar—NH₂), 7.2–6.5 (s, aromatic protons).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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

	x	y	z	U_iso*/U_eq
O1	0.55414 (16)	0.12426 (15)	0.49391 (5)	0.0128 (3)
O2	0.56105 (16)	0.40525 (15)	0.57785 (5)	0.0135 (3)
N1	0.2784 (2)	0.6233 (2)	0.59909 (7)	0.0198 (4)
N2	0.3172 (2)	−0.1449 (2)	0.48493 (6)	0.0165 (4)
C1	0.5343 (2)	0.0573 (2)	0.44011 (8)	0.0122 (4)
C2	0.6339 (3)	0.1177 (2)	0.39343 (8)	0.0155 (4)
C3	0.6015 (3)	0.0389 (2)	0.34126 (8)	0.0189 (5)
C4	0.4726 (3)	−0.0977 (3)	0.33620 (8)	0.0206 (5)
C5	0.3732 (3)	−0.1583 (2)	0.38334 (8)	0.0185 (5)
C6	0.4030 (2)	−0.0818 (2)	0.43586 (8)	0.0140 (4)
C7	0.7055 (2)	0.2471 (2)	0.50274 (7)	0.0133 (4)
C8	0.7142 (2)	0.2879 (2)	0.56454 (7)	0.0135 (4)
C9	0.5447 (2)	0.4543 (2)	0.63346 (7)	0.0126 (4)
C10	0.6617 (3)	0.3960 (2)	0.67652 (7)	0.0161 (4)
C11	0.6310 (3)	0.4574 (2)	0.73137 (7)	0.0201 (5)
C12	0.4849 (3)	0.5735 (3)	0.74229 (8)	0.0226 (5)
C13	0.3672 (3)	0.6319 (2)	0.69887 (8)	0.0202 (5)
C14	0.3954 (2)	0.5737 (2)	0.64386 (8)	0.0152 (4)
H1A	0.18400	0.69260	0.60490	0.0240*
H1B	0.30080	0.58440	0.56580	0.0240*
H2	0.72080	0.20920	0.39690	0.0190*
H2A	0.24250	−0.23440	0.48340	0.0200*
H2B	0.33910	−0.09410	0.51660	0.0200*
H3	0.66690	0.07840	0.30980	0.0230*
H4	0.45190	−0.14960	0.30130	0.0250*
H5	0.28680	−0.25020	0.37960	0.0220*
H7A	0.68280	0.35430	0.48150	0.0160*
H7B	0.82440	0.19630	0.49030	0.0160*
H8A	0.70290	0.18000	0.58620	0.0160*
H8B	0.83420	0.34300	0.57370	0.0160*
H10	0.75930	0.31700	0.66910	0.0190*
H11	0.70930	0.41990	0.76040	0.0240*
H12	0.46460	0.61320	0.77880	0.0270*
H13	0.26930	0.71010	0.70670	0.0240*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0127 (5)	0.0123 (5)	0.0134 (5)	−0.0049 (4)	0.0023 (4)	−0.0026 (4)
O2	0.0134 (5)	0.0118 (5)	0.0152 (6)	0.0031 (4)	−0.0009 (4)	−0.0019 (4)
N1	0.0167 (7)	0.0189 (7)	0.0237 (7)	0.0073 (5)	−0.0011 (6)	−0.0007 (6)
N2	0.0142 (6)	0.0153 (6)	0.0200 (7)	−0.0052 (5)	0.0008 (5)	−0.0004 (5)
C1	0.0125 (7)	0.0109 (6)	0.0131 (7)	0.0036 (6)	−0.0003 (6)	−0.0009 (6)
C2	0.0143 (8)	0.0136 (7)	0.0186 (8)	0.0011 (6)	0.0029 (6)	0.0013 (6)
C3	0.0227 (8)	0.0181 (8)	0.0159 (8)	0.0062 (7)	0.0032 (7)	0.0029 (6)
C4	0.0255 (9)	0.0201 (8)	0.0163 (8)	0.0057 (7)	−0.0058 (7)	−0.0037 (6)
C5	0.0185 (9)	0.0157 (8)	0.0212 (9)	0.0002 (6)	−0.0064 (6)	−0.0022 (7)
C6	0.0122 (7)	0.0127 (7)	0.0170 (8)	0.0027 (6)	−0.0023 (6)	0.0001 (6)
C7	0.0118 (7)	0.0107 (6)	0.0174 (7)	−0.0024 (5)	0.0011 (6)	−0.0020 (6)
C8	0.0118 (7)	0.0102 (7)	0.0185 (7)	0.0023 (6)	−0.0008 (6)	−0.0018 (6)
C9	0.0128 (7)	0.0088 (7)	0.0161 (8)	−0.0033 (6)	−0.0005 (6)	−0.0012 (6)
C10	0.0174 (8)	0.0129 (7)	0.0179 (8)	−0.0015 (6)	−0.0025 (7)	−0.0003 (6)
C11	0.0274 (9)	0.0179 (8)	0.0149 (8)	−0.0050 (7)	−0.0035 (7)	0.0018 (6)
C12	0.0326 (10)	0.0205 (9)	0.0148 (8)	−0.0060 (8)	0.0043 (7)	−0.0032 (7)
C13	0.0225 (10)	0.0158 (8)	0.0224 (9)	−0.0002 (7)	0.0072 (7)	−0.0027 (7)
C14	0.0140 (7)	0.0116 (7)	0.0201 (8)	−0.0008 (6)	0.0011 (7)	0.0004 (6)

Geometric parameters (Å, º) top

O1—C1	1.385 (2)	C9—C14	1.412 (2)
O1—C7	1.4331 (19)	C10—C11	1.403 (2)
O2—C8	1.4358 (19)	C11—C12	1.381 (3)
O2—C9	1.380 (2)	C12—C13	1.398 (3)
N1—C14	1.400 (2)	C13—C14	1.396 (3)
N2—C6	1.400 (2)	C2—H2	0.9300
N1—H1B	0.8600	C3—H3	0.9300
N1—H1A	0.8600	C4—H4	0.9300
N2—H2B	0.8600	C5—H5	0.9300
N2—H2A	0.8600	C7—H7A	0.9700
C1—C6	1.408 (2)	C7—H7B	0.9700
C1—C2	1.393 (3)	C8—H8A	0.9700
C2—C3	1.397 (3)	C8—H8B	0.9700
C3—C4	1.384 (3)	C10—H10	0.9300
C4—C5	1.401 (3)	C11—H11	0.9300
C5—C6	1.394 (3)	C12—H12	0.9300
C7—C8	1.505 (2)	C13—H13	0.9300
C9—C10	1.389 (2)

O1···O2	2.9203 (17)	C14···H1A^iv	3.0800
O1···N2	2.6470 (19)	H1A···H13	2.5000
O1···N2ⁱ	3.1602 (19)	H1A···O2ⁱ	2.4500
O1···C7ⁱⁱ	3.3308 (19)	H1A···C8ⁱ	3.0600
O2···N1	2.6405 (19)	H1A···C9ⁱ	2.6500
O2···C8ⁱⁱⁱ	3.3208 (19)	H1A···C14ⁱ	3.0800
O2···O1	2.9203 (17)	H1B···O2	2.3000
O2···N1^iv	3.2512 (19)	H1B···N2^v	2.8200
O1···H7Aⁱⁱ	2.7800	H1B···H2A^v	2.4300
O1···H2B	2.3100	H1B···N2ⁱ	2.7200
O1···H2Aⁱ	2.3700	H1B···H2Bⁱ	2.0400
O2···H1B	2.3000	H2···C7	2.5400
O2···H1A^iv	2.4500	H2···H7A	2.3100
O2···H8Aⁱⁱⁱ	2.6700	H2···H7B	2.3400
N1···O2	2.6405 (19)	H2···C3ⁱⁱⁱ	3.0900
N1···N2^v	3.247 (2)	H2···C4ⁱⁱⁱ	2.9900
N1···O2ⁱ	3.2512 (19)	H2···C5ⁱⁱⁱ	3.0600
N2···O1	2.6470 (19)	H2A···H1B^vi	2.4300
N2···O1^iv	3.1602 (19)	H2A···H5	2.4900
N2···N1^vi	3.247 (2)	H2A···O1^iv	2.3700
N1···H2Bⁱ	2.6900	H2A···C1^iv	2.7200
N1···H2B^v	2.9400	H2A···C6^iv	3.0400
N2···H1B^vi	2.8200	H2B···O1	2.3100
N2···H1B^iv	2.7200	H2B···N1^vi	2.9400
N2···H7Bⁱⁱ	2.8100	H2B···N1^iv	2.6900
C1···C7ⁱⁱ	3.336 (2)	H2B···H1B^iv	2.0400
C6···C7ⁱⁱ	3.445 (2)	H3···C12^xi	2.9900
C7···C6ⁱⁱⁱ	3.445 (2)	H4···C11^xii	2.9200
C7···C1ⁱⁱⁱ	3.336 (2)	H4···H11^xii	2.5400
C7···O1ⁱⁱⁱ	3.3308 (19)	H5···H2A	2.4900
C8···C9ⁱⁱ	3.462 (2)	H5···C1^iv	3.0600
C8···O2ⁱⁱ	3.3208 (19)	H7A···C2	2.7800
C9···C8ⁱⁱⁱ	3.462 (2)	H7A···H2	2.3100
C1···H7Aⁱⁱ	2.7100	H7A···O1ⁱⁱⁱ	2.7800
C1···H5ⁱ	3.0600	H7A···C1ⁱⁱⁱ	2.7100
C1···H2Aⁱ	2.7200	H7B···C2	2.7400
C2···H7B	2.7400	H7B···H2	2.3400
C2···H7A	2.7800	H7B···N2ⁱⁱⁱ	2.8100
C3···H2ⁱⁱ	3.0900	H7B···C6ⁱⁱⁱ	2.8700
C3···H12^vii	3.0600	H8A···C10	2.7200
C4···H11^viii	2.9200	H8A···H10	2.2700
C4···H2ⁱⁱ	2.9900	H8A···O2ⁱⁱ	2.6700
C5···H2ⁱⁱ	3.0600	H8A···C8ⁱⁱ	3.0700
C6···H2Aⁱ	3.0400	H8A···C9ⁱⁱ	2.7100
C6···H7Bⁱⁱ	2.8700	H8A···H8Bⁱⁱ	2.5800
C7···H2	2.5400	H8B···C10	2.7600
C8···H10	2.5200	H8B···H10	2.3400
C8···H1A^iv	3.0600	H8B···H8Aⁱⁱⁱ	2.5800
C8···H8Aⁱⁱⁱ	3.0700	H10···C8	2.5200
C9···H1A^iv	2.6500	H10···H8A	2.2700
C9···H8Aⁱⁱⁱ	2.7100	H10···H8B	2.3400
C10···H8A	2.7200	H10···C13ⁱⁱ	3.0700
C10···H8B	2.7600	H11···H4^ix	2.5400
C11···H4^ix	2.9200	H11···C4^xiii	2.9200
C12···H3^x	2.9900	H12···C3^xiv	3.0600
C13···H10ⁱⁱⁱ	3.0700	H13···H1A	2.5000

C1—O1—C7	116.69 (12)	N1—C14—C9	118.66 (16)
C8—O2—C9	116.21 (12)	N1—C14—C13	123.02 (15)
C14—N1—H1A	120.00	C1—C2—H2	121.00
C14—N1—H1B	120.00	C3—C2—H2	120.00
H1A—N1—H1B	120.00	C2—C3—H3	120.00
C6—N2—H2A	120.00	C4—C3—H3	120.00
C6—N2—H2B	120.00	C3—C4—H4	120.00
H2A—N2—H2B	120.00	C5—C4—H4	120.00
C2—C1—C6	121.44 (17)	C4—C5—H5	120.00
O1—C1—C2	124.51 (14)	C6—C5—H5	120.00
O1—C1—C6	114.05 (15)	O1—C7—H7A	110.00
C1—C2—C3	119.09 (16)	O1—C7—H7B	110.00
C2—C3—C4	120.33 (18)	C8—C7—H7A	110.00
C3—C4—C5	120.34 (18)	C8—C7—H7B	110.00
C4—C5—C6	120.42 (17)	H7A—C7—H7B	108.00
N2—C6—C5	122.74 (14)	O2—C8—H8A	110.00
C1—C6—C5	118.38 (16)	O2—C8—H8B	110.00
N2—C6—C1	118.75 (16)	C7—C8—H8A	110.00
O1—C7—C8	107.90 (12)	C7—C8—H8B	110.00
O2—C8—C7	108.19 (12)	H8A—C8—H8B	108.00
C10—C9—C14	121.27 (16)	C9—C10—H10	120.00
O2—C9—C14	113.80 (14)	C11—C10—H10	120.00
O2—C9—C10	124.93 (14)	C10—C11—H11	120.00
C9—C10—C11	119.30 (17)	C12—C11—H11	120.00
C10—C11—C12	120.13 (17)	C11—C12—H12	120.00
C11—C12—C13	120.46 (17)	C13—C12—H12	120.00
C12—C13—C14	120.57 (17)	C12—C13—H13	120.00
C9—C14—C13	118.27 (16)	C14—C13—H13	120.00

C7—O1—C1—C2	−8.7 (2)	C4—C5—C6—N2	−175.58 (17)
C7—O1—C1—C6	170.81 (12)	C4—C5—C6—C1	0.2 (3)
C1—O1—C7—C8	−174.15 (12)	O1—C7—C8—O2	−75.68 (14)
C8—O2—C9—C14	178.22 (12)	O2—C9—C10—C11	179.40 (15)
C9—O2—C8—C7	178.74 (12)	C14—C9—C10—C11	−0.2 (3)
C8—O2—C9—C10	−1.4 (2)	O2—C9—C14—N1	2.5 (2)
O1—C1—C6—N2	−4.0 (2)	O2—C9—C14—C13	−179.83 (14)
C2—C1—C6—C5	−0.4 (2)	C10—C9—C14—N1	−177.96 (15)
O1—C1—C6—C5	−179.91 (14)	C10—C9—C14—C13	−0.2 (2)
C6—C1—C2—C3	0.4 (3)	C9—C10—C11—C12	0.5 (3)
O1—C1—C2—C3	179.88 (15)	C10—C11—C12—C13	−0.5 (3)
C2—C1—C6—N2	175.55 (15)	C11—C12—C13—C14	0.1 (3)
C1—C2—C3—C4	−0.2 (3)	C12—C13—C14—N1	177.90 (17)
C2—C3—C4—C5	0.0 (3)	C12—C13—C14—C9	0.3 (3)
C3—C4—C5—C6	0.0 (3)

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+3/2, y−1/2, z; (iii) −x+3/2, y+1/2, z; (iv) −x+1/2, y−1/2, z; (v) x, y+1, z; (vi) x, y−1, z; (vii) −x+1, −y+1, z−1/2; (viii) x−1/2, −y+1/2, z−1/2; (ix) −x+1, −y, z+1/2; (x) x−1/2, −y+1/2, z+1/2; (xi) x+1/2, −y+1/2, z−1/2; (xii) −x+1, −y, z−1/2; (xiii) x+1/2, −y+1/2, z+1/2; (xiv) −x+1, −y+1, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.45	3.2512 (19)	155
N1—H1B···O2	0.86	2.30	2.6405 (19)	104
N2—H2A···O1^iv	0.86	2.37	3.1602 (19)	154
N2—H2B···O1	0.86	2.31	2.6470 (19)	104

Symmetry codes: (i) −x+1/2, y+1/2, z; (iv) −x+1/2, y−1/2, z.

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Ortho­rhom­bic polymorph of 1,2-bis­(2-amino­phen­oxy)ethane

Supporting information

Key indicators

checkCIF/PLATON results

Orthorhombic polymorph of 1,2-bis(2-aminophenoxy)ethane