1,1-Dibenzoyl-3,3-dimethyl­urea

The mol­ecules of 1,1-dibenzoyl-3,3-dimethyl­urea, C₁₇H₁₆N₂O₃, inter­act through an inter­molecular C—H...O hydrogen bond and several C—H...π inter­actions, resulting in a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.105
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_2_C           Chirality of atom sites is inverted?
           From the CIF: _refine_ls_abs_structure_Flack    4.000
           From the CIF: _refine_ls_abs_structure_Flack_su    2.000
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...       2.00
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       4.00
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C4      ..       5.11 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
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           26.00
           From the CIF: _reflns_number_total               1803
           Count of symmetry unique reflns         1806
           Completeness (_total/calc)             99.83%
           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
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: X-SEED.

1,1-dibenzoyl-3,3-dimethylurea

Crystal data

C17H16N2O3	Dx = 1.267 Mg m^−3
Mr = 296.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8844 reflections
a = 6.002 (3) Å	θ = 2.4–26.0°
b = 8.822 (5) Å	µ = 0.09 mm^−1
c = 29.339 (15) Å	T = 100 K
V = 1553.5 (14) Å^3	Needle, colourless
Z = 4	0.30 × 0.10 × 0.05 mm
F(000) = 624

Data collection

Bruker SMART APEX CCD diffractometer	1803 independent reflections
Radiation source: fine-focus sealed tube	1483 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 2002)	h = −7→3
Tmin = 0.964, Tmax = 0.996	k = −10→10
8844 measured reflections	l = −32→36

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 0.2226P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.009
1803 reflections	Δρmax = 0.15 e Å^−3
201 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: heavy-atom method	Absolute structure parameter: 4 (2)

Special details

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. Friedel opposites were averaged using MERG 3 prior to refinement. The number of Friedel pairs (1247) was determined prior to final refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.1132 (4)	0.0158 (2)	0.12916 (7)	0.0408 (6)
O3	0.0492 (4)	0.2525 (2)	0.10065 (7)	0.0614 (6)
O1	0.0251 (4)	0.0044 (3)	0.20433 (7)	0.0626 (7)
C11	0.0821 (5)	0.1203 (3)	0.09306 (10)	0.0457 (7)
C1	0.2852 (5)	0.1937 (3)	0.18474 (9)	0.0412 (7)
C6	0.4811 (5)	0.2124 (3)	0.16069 (10)	0.0488 (8)
H6	0.5113	0.1500	0.1350	0.059*
N2	0.1380 (5)	−0.2468 (3)	0.13802 (8)	0.0530 (7)
C2	0.1284 (5)	0.0685 (3)	0.17486 (9)	0.0431 (7)
C12	0.0961 (5)	0.0571 (3)	0.04618 (9)	0.0467 (7)
O2	−0.1714 (4)	−0.1439 (3)	0.10723 (8)	0.0677 (7)
C3	0.0118 (6)	−0.1329 (3)	0.12396 (10)	0.0484 (8)
C9	0.3920 (6)	0.3966 (4)	0.23429 (10)	0.0561 (8)
H9	0.3607	0.4617	0.2593	0.067*
C10	0.2415 (5)	0.2862 (3)	0.22190 (9)	0.0471 (7)
H10	0.1079	0.2734	0.2388	0.057*
C8	0.5866 (6)	0.4120 (4)	0.21049 (11)	0.0574 (9)
H8	0.6916	0.4868	0.2195	0.069*
C7	0.6324 (6)	0.3209 (3)	0.17367 (11)	0.0571 (8)
H7	0.7678	0.3329	0.1573	0.068*
C13	0.2491 (6)	−0.0527 (4)	0.03413 (11)	0.0605 (9)
H13	0.3505	−0.0914	0.0561	0.073*
C17	−0.0459 (6)	0.1156 (4)	0.01378 (11)	0.0642 (10)
H17	−0.1475	0.1939	0.0217	0.077*
C4	0.3576 (6)	−0.2334 (4)	0.15740 (13)	0.0687 (10)
H4A	0.4257	−0.1381	0.1473	0.103*
H4B	0.4496	−0.3188	0.1473	0.103*
H4C	0.3469	−0.2341	0.1907	0.103*
C14	0.2535 (8)	−0.1060 (4)	−0.01037 (12)	0.0806 (12)
H14	0.3574	−0.1821	−0.0189	0.097*
C5	0.0392 (8)	−0.3986 (4)	0.13870 (15)	0.0896 (14)
H5A	0.0991	−0.4558	0.1646	0.134*
H5B	0.0755	−0.4514	0.1103	0.134*
H5C	−0.1229	−0.3902	0.1417	0.134*
C15	0.1089 (9)	−0.0494 (5)	−0.04168 (13)	0.0910 (14)
H15	0.1120	−0.0868	−0.0720	0.109*
C16	−0.0403 (8)	0.0603 (5)	−0.03012 (12)	0.0829 (13)
H16	−0.1406	0.0987	−0.0523	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0457 (14)	0.0361 (12)	0.0407 (13)	−0.0066 (12)	0.0056 (11)	0.0036 (10)
O3	0.0917 (18)	0.0382 (11)	0.0541 (13)	0.0088 (13)	0.0050 (12)	−0.0005 (10)
O1	0.0720 (16)	0.0629 (14)	0.0528 (13)	−0.0137 (13)	0.0209 (12)	0.0068 (11)
C11	0.0464 (17)	0.0392 (17)	0.0515 (18)	−0.0014 (15)	0.0070 (14)	0.0010 (13)
C1	0.0439 (17)	0.0402 (16)	0.0394 (15)	0.0039 (13)	0.0023 (13)	0.0056 (12)
C6	0.0506 (18)	0.0470 (18)	0.0489 (17)	−0.0030 (15)	0.0112 (15)	−0.0082 (14)
N2	0.0609 (17)	0.0356 (13)	0.0626 (16)	−0.0071 (14)	−0.0061 (14)	0.0041 (12)
C2	0.0451 (17)	0.0383 (15)	0.0461 (16)	0.0034 (15)	0.0109 (14)	0.0064 (13)
C12	0.0523 (19)	0.0420 (16)	0.0458 (17)	−0.0029 (16)	0.0067 (15)	0.0031 (13)
O2	0.0558 (15)	0.0671 (15)	0.0802 (16)	−0.0215 (13)	−0.0121 (12)	0.0119 (13)
C3	0.0496 (19)	0.0468 (18)	0.0487 (17)	−0.0119 (17)	0.0081 (15)	0.0017 (14)
C9	0.064 (2)	0.057 (2)	0.0469 (18)	0.0067 (19)	−0.0029 (16)	−0.0122 (15)
C10	0.0496 (18)	0.0511 (18)	0.0407 (15)	0.0047 (17)	0.0055 (14)	−0.0017 (13)
C8	0.058 (2)	0.0522 (19)	0.062 (2)	−0.0066 (18)	−0.0075 (17)	−0.0080 (16)
C7	0.0482 (19)	0.057 (2)	0.066 (2)	−0.0060 (17)	0.0062 (16)	−0.0050 (17)
C13	0.066 (2)	0.062 (2)	0.0534 (19)	0.011 (2)	0.0050 (17)	0.0004 (16)
C17	0.076 (3)	0.059 (2)	0.057 (2)	0.011 (2)	−0.0025 (18)	0.0014 (17)
C4	0.065 (2)	0.051 (2)	0.090 (2)	0.0056 (19)	−0.002 (2)	0.0055 (19)
C14	0.102 (3)	0.081 (3)	0.059 (2)	0.021 (3)	0.020 (2)	−0.012 (2)
C5	0.107 (4)	0.044 (2)	0.118 (3)	−0.022 (2)	−0.020 (3)	0.011 (2)
C15	0.125 (4)	0.098 (3)	0.050 (2)	0.009 (3)	0.005 (3)	−0.013 (2)
C16	0.098 (3)	0.096 (3)	0.054 (2)	0.008 (3)	−0.018 (2)	0.000 (2)

Geometric parameters (Å, º)

N1—C11	1.416 (3)	C10—H10	0.9500
N1—C2	1.422 (3)	C8—C7	1.374 (4)
N1—C3	1.454 (4)	C8—H8	0.9500
O3—C11	1.203 (3)	C7—H7	0.9500
O1—C2	1.205 (3)	C13—C14	1.388 (5)
C11—C12	1.486 (4)	C13—H13	0.9500
C1—C6	1.381 (4)	C17—C16	1.378 (5)
C1—C10	1.387 (4)	C17—H17	0.9500
C1—C2	1.479 (4)	C4—H4A	0.9800
C6—C7	1.373 (4)	C4—H4B	0.9800
C6—H6	0.9500	C4—H4C	0.9800
N2—C3	1.324 (4)	C14—C15	1.359 (6)
N2—C4	1.440 (4)	C14—H14	0.9500
N2—C5	1.464 (4)	C5—H5A	0.9800
C12—C17	1.377 (4)	C5—H5B	0.9800
C12—C13	1.381 (4)	C5—H5C	0.9800
O2—C3	1.208 (4)	C15—C16	1.361 (6)
C9—C8	1.368 (5)	C15—H15	0.9500
C9—C10	1.377 (4)	C16—H16	0.9500
C9—H9	0.9500
C11—N1—C2	120.0 (2)	C7—C8—H8	119.5
C11—N1—C3	117.0 (2)	C6—C7—C8	119.6 (3)
C2—N1—C3	114.9 (2)	C6—C7—H7	120.2
O3—C11—N1	120.9 (3)	C8—C7—H7	120.2
O3—C11—C12	122.9 (3)	C12—C13—C14	119.4 (3)
N1—C11—C12	116.1 (2)	C12—C13—H13	120.3
C6—C1—C10	119.5 (3)	C14—C13—H13	120.3
C6—C1—C2	122.1 (3)	C12—C17—C16	119.8 (3)
C10—C1—C2	118.2 (3)	C12—C17—H17	120.1
C7—C6—C1	120.3 (3)	C16—C17—H17	120.1
C7—C6—H6	119.8	N2—C4—H4A	109.5
C1—C6—H6	119.8	N2—C4—H4B	109.5
C3—N2—C4	125.7 (3)	H4A—C4—H4B	109.5
C3—N2—C5	117.8 (3)	N2—C4—H4C	109.5
C4—N2—C5	116.1 (3)	H4A—C4—H4C	109.5
O1—C2—N1	119.3 (3)	H4B—C4—H4C	109.5
O1—C2—C1	122.5 (3)	C15—C14—C13	119.9 (4)
N1—C2—C1	118.0 (2)	C15—C14—H14	120.0
C17—C12—C13	119.9 (3)	C13—C14—H14	120.0
C17—C12—C11	117.6 (3)	N2—C5—H5A	109.5
C13—C12—C11	122.5 (3)	N2—C5—H5B	109.5
O2—C3—N2	125.9 (3)	H5A—C5—H5B	109.5
O2—C3—N1	119.7 (3)	N2—C5—H5C	109.5
N2—C3—N1	114.4 (3)	H5A—C5—H5C	109.5
C8—C9—C10	119.7 (3)	H5B—C5—H5C	109.5
C8—C9—H9	120.1	C14—C15—C16	120.9 (4)
C10—C9—H9	120.1	C14—C15—H15	119.6
C9—C10—C1	120.0 (3)	C16—C15—H15	119.6
C9—C10—H10	120.0	C15—C16—C17	120.1 (4)
C1—C10—H10	120.0	C15—C16—H16	120.0
C9—C8—C7	120.9 (3)	C17—C16—H16	120.0
C9—C8—H8	119.5
C2—N1—C11—O3	−6.4 (4)	C11—N1—C3—O2	−39.6 (4)
C3—N1—C11—O3	140.7 (3)	C2—N1—C3—O2	109.2 (3)
C2—N1—C11—C12	172.7 (3)	C11—N1—C3—N2	139.3 (3)
C3—N1—C11—C12	−40.2 (4)	C2—N1—C3—N2	−72.0 (3)
C10—C1—C6—C7	0.6 (4)	C8—C9—C10—C1	−1.6 (5)
C2—C1—C6—C7	−173.7 (3)	C6—C1—C10—C9	0.6 (4)
C11—N1—C2—O1	134.5 (3)	C2—C1—C10—C9	175.1 (3)
C3—N1—C2—O1	−13.2 (4)	C10—C9—C8—C7	1.4 (5)
C11—N1—C2—C1	−50.1 (4)	C1—C6—C7—C8	−0.7 (5)
C3—N1—C2—C1	162.2 (2)	C9—C8—C7—C6	−0.2 (5)
C6—C1—C2—O1	143.6 (3)	C17—C12—C13—C14	−1.8 (5)
C10—C1—C2—O1	−30.7 (4)	C11—C12—C13—C14	−179.7 (3)
C6—C1—C2—N1	−31.6 (4)	C13—C12—C17—C16	2.4 (5)
C10—C1—C2—N1	154.1 (3)	C11—C12—C17—C16	−179.6 (3)
O3—C11—C12—C17	−37.7 (5)	C12—C13—C14—C15	0.4 (6)
N1—C11—C12—C17	143.2 (3)	C13—C14—C15—C16	0.4 (7)
O3—C11—C12—C13	140.2 (3)	C14—C15—C16—C17	0.1 (7)
N1—C11—C12—C13	−38.8 (4)	C12—C17—C16—C15	−1.5 (6)
C4—N2—C3—O2	179.1 (3)	O2—C3—C11—O3	84.3 (4)
C5—N2—C3—O2	−7.9 (5)	O2—C3—C2—O1	76.8 (3)
C4—N2—C3—N1	0.4 (4)	O1—C2—C11—O3	109.1 (3)
C5—N2—C3—N1	173.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3^i	0.95	2.47	3.349 (4)	153

Symmetry code: (i) x+1, y, z.