4-Methyl-1H-1,5-benzodiazepin-2(3H)-one

In the title compound, C₁₀H₁₀N₂O, the seven-membered heterocycle displays a half-chair conformation. In the crystal, N—H...O and C—H...O hydrogen bonds link the mol­ecules into chains propagating along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.028
• wR factor = 0.086
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTY03_ALERT_1_C  The _exptl_absorpt_correction_type has been given as none.
            However values have been given for Tmin and Tmax. Remove
            these if an absorption correction has not been applied.
  From the CIF: _exptl_absorpt_correction_T_min   0.974
  From the CIF: _exptl_absorpt_correction_T_max   0.984
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.300
           From the CIF: _refine_ls_abs_structure_Flack_su    0.200

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

4-Methyl-1H-1,5-benzodiazepin-2(3H)-one

Crystal data

C10H10N2O	Dx = 1.243 Mg m^−3
Mr = 174.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 245 reflections
a = 7.5676 (2) Å	θ = 0.5–32°
b = 10.7802 (2) Å	µ = 0.08 mm^−1
c = 11.4092 (3) Å	T = 296 K
V = 930.77 (4) Å^3	Prism, colourless
Z = 4	0.32 × 0.28 × 0.20 mm
F(000) = 368

Data collection

Bruker X8 APEXII CCD area-detector diffractometer	1747 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 26.0°, θmin = 3.6°
ω and φ scans	h = −9→9
25369 measured reflections	k = −13→13
1825 independent reflections	l = −13→14

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.0631P)^2 + 0.0577P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.086	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.14 e Å^−3
1825 reflections	Δρmin = −0.15 e Å^−3
123 parameters	Absolute structure: Flack x determined using 705 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.3 (2)
Primary atom site location: dual

Special details

Geometry. 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.

Refinement. The H atoms were located in a difference map and treated as riding with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and with U_iso(H) = 1.2–1.5Ueq(C, N).

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

	x	y	z	Uiso*/Ueq
C1	0.0092 (2)	0.51751 (13)	0.91727 (13)	0.0373 (3)
C9	0.2131 (2)	0.35141 (15)	0.97843 (13)	0.0379 (3)
C6	0.1120 (2)	0.58213 (14)	0.83489 (13)	0.0410 (4)
C8	0.3621 (2)	0.44253 (15)	0.96221 (14)	0.0402 (3)
H8A	0.4723	0.4076	0.9906	0.048*
H8B	0.3383	0.5185	1.0049	0.048*
C2	−0.1472 (2)	0.56990 (16)	0.95911 (15)	0.0466 (4)
H2	−0.2167	0.5258	1.0119	0.056*
C5	0.0527 (3)	0.69915 (16)	0.79881 (16)	0.0550 (5)
H5	0.1177	0.7428	0.7433	0.066*
C7	0.3736 (2)	0.46818 (16)	0.83226 (14)	0.0439 (4)
C3	−0.2001 (3)	0.68650 (18)	0.92309 (17)	0.0601 (5)
H3	−0.3034	0.7213	0.9524	0.072*
C4	−0.0983 (3)	0.75106 (17)	0.84313 (19)	0.0641 (6)
H4	−0.1325	0.8300	0.8193	0.077*
C10	0.5213 (3)	0.4081 (3)	0.76664 (19)	0.0667 (6)
H10A	0.5044	0.4201	0.6840	0.100*
H10B	0.5230	0.3209	0.7837	0.100*
H10C	0.6316	0.4445	0.7900	0.100*
N1	0.05078 (16)	0.39599 (12)	0.95461 (12)	0.0394 (3)
N2	0.26065 (19)	0.53402 (13)	0.77731 (12)	0.0459 (3)
O1	0.23581 (16)	0.24292 (11)	1.00743 (13)	0.0519 (3)
H1N	−0.042 (3)	0.3435 (19)	0.9707 (19)	0.057 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0376 (7)	0.0352 (7)	0.0392 (7)	0.0012 (6)	−0.0087 (6)	0.0009 (6)
C9	0.0332 (7)	0.0387 (8)	0.0419 (7)	0.0000 (6)	−0.0015 (6)	0.0047 (6)
C6	0.0467 (8)	0.0381 (7)	0.0382 (7)	−0.0027 (7)	−0.0076 (6)	0.0028 (6)
C8	0.0325 (7)	0.0438 (8)	0.0443 (8)	−0.0043 (6)	−0.0057 (6)	0.0036 (6)
C2	0.0424 (8)	0.0501 (9)	0.0473 (8)	0.0056 (7)	−0.0035 (7)	0.0015 (7)
C5	0.0670 (12)	0.0448 (9)	0.0531 (10)	−0.0003 (9)	−0.0084 (9)	0.0125 (8)
C7	0.0378 (8)	0.0483 (8)	0.0454 (8)	−0.0078 (7)	0.0004 (6)	0.0011 (7)
C3	0.0616 (11)	0.0585 (11)	0.0601 (10)	0.0239 (9)	−0.0067 (9)	−0.0046 (9)
C4	0.0828 (14)	0.0448 (9)	0.0648 (12)	0.0172 (10)	−0.0152 (11)	0.0076 (9)
C10	0.0471 (10)	0.0954 (16)	0.0576 (11)	0.0069 (11)	0.0063 (8)	−0.0033 (11)
N1	0.0317 (6)	0.0351 (6)	0.0514 (7)	−0.0029 (5)	−0.0022 (5)	0.0078 (5)
N2	0.0466 (7)	0.0498 (8)	0.0413 (6)	−0.0051 (7)	−0.0003 (6)	0.0054 (6)
O1	0.0383 (6)	0.0411 (6)	0.0764 (8)	0.0023 (5)	−0.0022 (6)	0.0167 (5)

Geometric parameters (Å, º)

C1—C2	1.395 (2)	C2—H2	0.9300
C1—C6	1.405 (2)	C5—C4	1.370 (3)
C1—N1	1.4131 (19)	C5—H5	0.9300
C9—O1	1.2275 (19)	C7—N2	1.276 (2)
C9—N1	1.347 (2)	C7—C10	1.493 (3)
C9—C8	1.507 (2)	C3—C4	1.382 (3)
C6—C5	1.401 (2)	C3—H3	0.9300
C6—N2	1.402 (2)	C4—H4	0.9300
C8—C7	1.511 (2)	C10—H10A	0.9600
C8—H8A	0.9700	C10—H10B	0.9600
C8—H8B	0.9700	C10—H10C	0.9600
C2—C3	1.382 (2)	N1—H1N	0.918 (18)
C2—C1—C6	119.86 (14)	C6—C5—H5	119.1
C2—C1—N1	117.45 (14)	N2—C7—C10	119.78 (16)
C6—C1—N1	122.54 (14)	N2—C7—C8	123.06 (15)
O1—C9—N1	121.47 (14)	C10—C7—C8	117.11 (16)
O1—C9—C8	123.32 (14)	C4—C3—C2	119.55 (18)
N1—C9—C8	115.16 (13)	C4—C3—H3	120.2
C5—C6—N2	116.89 (15)	C2—C3—H3	120.2
C5—C6—C1	117.76 (16)	C5—C4—C3	120.20 (17)
N2—C6—C1	125.06 (14)	C5—C4—H4	119.9
C9—C8—C7	106.43 (13)	C3—C4—H4	119.9
C9—C8—H8A	110.4	C7—C10—H10A	109.5
C7—C8—H8A	110.4	C7—C10—H10B	109.5
C9—C8—H8B	110.4	H10A—C10—H10B	109.5
C7—C8—H8B	110.4	C7—C10—H10C	109.5
H8A—C8—H8B	108.6	H10A—C10—H10C	109.5
C3—C2—C1	120.80 (17)	H10B—C10—H10C	109.5
C3—C2—H2	119.6	C9—N1—C1	126.51 (13)
C1—C2—H2	119.6	C9—N1—H1N	115.8 (14)
C4—C5—C6	121.79 (18)	C1—N1—H1N	117.5 (14)
C4—C5—H5	119.1	C7—N2—C6	120.87 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.92 (2)	1.94 (2)	2.8481 (17)	169 (2)
C8—H8A···O1^ii	0.97	2.57	3.480 (2)	156

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