Methyl N-[(2-hydroxy­naphthalen-1-yl)(phen­yl)meth­yl]carbamate

Inter­molecular O—H...O and intra­molecular N—H...O hydrogen bonds are effective in the stabilization of the crystal structure of the title compound, C₁₉H₁₇NO₃.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.070
• wR factor = 0.133
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.85 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C1     -   H1A    ...       0.84 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C19 H17 N O3

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

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-STEP32 (Stoe & Cie, 2000); software used to prepare material for publication: SHELXL97.

Methyl N-[(2-hydroxynaphthalen-1-yl)(phenyl)methyl]carbamate

Crystal data

C19H17NO3	F(000) = 648
Mr = 307.34	Dx = 1.264 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 9.217 (3) Å	θ = 2.3–26.8°
b = 18.106 (5) Å	µ = 0.09 mm^−1
c = 11.305 (4) Å	T = 294 K
β = 121.11 (2)°	Prism, yellow
V = 1615.4 (10) Å^3	0.3 × 0.15 × 0.1 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	2208 reflections with I > 2σ(I)
rotation method scans	Rint = 0.058
Absorption correction: numerical shape of crystal determined optically	θmax = 26.8°, θmin = 2.3°
Tmin = 0.985, Tmax = 0.991	h = −11→11
12313 measured reflections	k = −22→22
3450 independent reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.070	w = 1/[σ^2(Fo^2) + (0.0376P)^2 + 0.466P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.133	(Δ/σ)max = 0.002
S = 1.16	Δρmax = 0.13 e Å^−3
3450 reflections	Δρmin = −0.15 e Å^−3
276 parameters

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

	x	y	z	Uiso*/Ueq
C1	−0.0136 (10)	−0.4678 (2)	0.8023 (7)	0.1111 (19)
H1A	0.028 (5)	−0.487 (2)	0.759 (5)	0.125 (15)*
H1B	0.021 (6)	−0.488 (2)	0.892 (5)	0.143 (18)*
H1C	−0.135 (8)	−0.469 (3)	0.757 (6)	0.20 (3)*
C2	−0.0175 (3)	−0.34803 (12)	0.8829 (2)	0.0456 (6)
C3	−0.0332 (3)	−0.21664 (12)	0.9311 (2)	0.0450 (6)
H3	−0.070 (3)	−0.2421 (13)	0.986 (2)	0.052 (7)*
C4	0.1186 (3)	−0.16862 (12)	1.0272 (2)	0.0466 (6)
C5	0.2649 (5)	−0.20102 (17)	1.1334 (3)	0.0740 (9)
H5	0.265 (4)	−0.2519 (18)	1.143 (3)	0.081 (9)*
C6	0.4040 (5)	−0.1597 (2)	1.2233 (4)	0.0878 (11)
H6	0.501 (5)	−0.184 (2)	1.296 (4)	0.125 (14)*
C7	0.3997 (5)	−0.08495 (19)	1.2101 (3)	0.0774 (9)
H7	0.498 (4)	−0.0548 (18)	1.267 (4)	0.094 (11)*
C8	0.2574 (4)	−0.05140 (16)	1.1065 (3)	0.0699 (9)
H8	0.250 (4)	0.0019 (18)	1.092 (3)	0.087 (10)*
C9	0.1170 (4)	−0.09289 (14)	1.0160 (3)	0.0563 (7)
H9	0.015 (4)	−0.0697 (15)	0.943 (3)	0.066 (8)*
C10	−0.1840 (3)	−0.17541 (11)	0.8165 (2)	0.0439 (6)
C11	−0.1863 (3)	−0.15374 (13)	0.6990 (3)	0.0460 (6)
C12	−0.3272 (4)	−0.11778 (16)	0.5899 (3)	0.0608 (7)
H12	−0.326 (4)	−0.1044 (15)	0.506 (3)	0.076 (9)*
C13	−0.4649 (4)	−0.10303 (18)	0.5988 (4)	0.0707 (9)
H13	−0.559 (4)	−0.0796 (17)	0.526 (3)	0.083 (10)*
C14	−0.4696 (3)	−0.12094 (14)	0.7181 (3)	0.0606 (7)
C15	−0.6103 (4)	−0.1027 (2)	0.7314 (6)	0.0856 (11)
H15	−0.705 (5)	−0.078 (2)	0.651 (4)	0.104 (13)*
C16	−0.6107 (6)	−0.1184 (3)	0.8466 (7)	0.1078 (17)
H16	−0.695 (5)	−0.106 (2)	0.857 (4)	0.113 (13)*
C17	−0.4723 (7)	−0.1531 (2)	0.9563 (6)	0.1033 (14)
H17	−0.457 (5)	−0.167 (2)	1.046 (4)	0.116 (14)*
C18	−0.3326 (5)	−0.17207 (17)	0.9497 (4)	0.0725 (9)
H18	−0.241 (4)	−0.1958 (16)	1.023 (3)	0.072 (10)*
C19	−0.3274 (3)	−0.15719 (13)	0.8287 (3)	0.0522 (7)
N1	0.0192 (3)	−0.27791 (11)	0.8766 (2)	0.0519 (6)
H1D	0.060 (3)	−0.2668 (15)	0.827 (3)	0.066 (9)*
O1	0.0281 (3)	−0.39066 (9)	0.8112 (2)	0.0698 (6)
O2	−0.0809 (3)	−0.37217 (9)	0.9462 (2)	0.0673 (6)
O3	−0.0446 (2)	−0.16728 (10)	0.6918 (2)	0.0569 (5)
H3B	−0.062 (4)	−0.1536 (15)	0.614 (3)	0.065 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.209 (7)	0.0470 (19)	0.129 (4)	−0.018 (3)	0.124 (5)	−0.029 (2)
C2	0.0619 (16)	0.0374 (12)	0.0405 (13)	−0.0013 (11)	0.0286 (13)	−0.0032 (10)
C3	0.0678 (17)	0.0329 (11)	0.0502 (15)	0.0017 (11)	0.0416 (14)	0.0011 (10)
C4	0.0655 (17)	0.0381 (13)	0.0402 (14)	0.0066 (11)	0.0301 (14)	0.0021 (10)
C5	0.100 (3)	0.0429 (16)	0.0569 (19)	0.0151 (16)	0.0247 (19)	0.0062 (13)
C6	0.093 (3)	0.070 (2)	0.053 (2)	0.017 (2)	0.004 (2)	−0.0027 (17)
C7	0.078 (2)	0.071 (2)	0.056 (2)	−0.0025 (19)	0.0146 (19)	−0.0123 (16)
C8	0.079 (2)	0.0442 (16)	0.063 (2)	−0.0019 (15)	0.0198 (19)	−0.0030 (14)
C9	0.0625 (18)	0.0426 (15)	0.0501 (17)	0.0036 (13)	0.0194 (16)	0.0028 (12)
C10	0.0545 (15)	0.0341 (11)	0.0494 (14)	−0.0065 (10)	0.0313 (13)	−0.0084 (10)
C11	0.0513 (15)	0.0439 (13)	0.0467 (15)	−0.0047 (11)	0.0282 (13)	−0.0077 (11)
C12	0.0633 (19)	0.0641 (18)	0.0473 (17)	−0.0004 (14)	0.0231 (16)	−0.0016 (13)
C13	0.0541 (19)	0.071 (2)	0.064 (2)	0.0014 (16)	0.0144 (19)	−0.0099 (16)
C14	0.0474 (16)	0.0494 (15)	0.084 (2)	−0.0096 (12)	0.0335 (17)	−0.0229 (14)
C15	0.057 (2)	0.077 (2)	0.125 (4)	−0.0095 (18)	0.049 (3)	−0.034 (2)
C16	0.093 (3)	0.104 (3)	0.171 (5)	−0.011 (3)	0.100 (4)	−0.034 (3)
C17	0.132 (4)	0.096 (3)	0.142 (4)	−0.003 (3)	0.114 (4)	−0.010 (3)
C18	0.091 (3)	0.0653 (19)	0.096 (3)	0.0008 (18)	0.073 (2)	−0.0024 (18)
C19	0.0600 (16)	0.0384 (13)	0.0706 (18)	−0.0130 (12)	0.0425 (16)	−0.0152 (12)
N1	0.0780 (16)	0.0358 (10)	0.0639 (14)	0.0005 (10)	0.0523 (14)	−0.0014 (9)
O1	0.1168 (17)	0.0402 (9)	0.0835 (14)	−0.0036 (10)	0.0737 (14)	−0.0135 (9)
O2	0.1139 (17)	0.0454 (10)	0.0716 (13)	−0.0195 (10)	0.0685 (13)	−0.0129 (9)
O3	0.0683 (13)	0.0657 (11)	0.0512 (11)	0.0042 (9)	0.0412 (11)	0.0081 (9)

Geometric parameters (Å, º)

C1—O1	1.438 (4)	C9—H9	0.97 (3)
C1—H1A	0.84 (4)	C10—C11	1.375 (3)
C1—H1B	0.96 (5)	C10—C19	1.436 (3)
C1—H1C	0.96 (6)	C11—O3	1.372 (3)
C2—O2	1.215 (3)	C11—C12	1.406 (4)
C2—N1	1.325 (3)	C12—C13	1.351 (4)
C2—O1	1.335 (3)	C12—H12	0.98 (3)
C3—N1	1.467 (3)	C13—C14	1.410 (4)
C3—C10	1.519 (3)	C13—H13	0.94 (3)
C3—C4	1.524 (3)	C14—C15	1.420 (4)
C3—H3	0.96 (2)	C14—C19	1.421 (4)
C4—C9	1.376 (3)	C15—C16	1.334 (6)
C4—C5	1.390 (4)	C15—H15	0.98 (4)
C5—C6	1.374 (5)	C16—C17	1.388 (7)
C5—H5	0.93 (3)	C16—H16	0.87 (4)
C6—C7	1.361 (5)	C17—C18	1.372 (5)
C6—H6	0.95 (4)	C17—H17	0.98 (4)
C7—C8	1.369 (4)	C18—C19	1.418 (4)
C7—H7	0.96 (3)	C18—H18	0.93 (3)
C8—C9	1.385 (4)	N1—H1D	0.84 (3)
C8—H8	0.97 (3)	O3—H3B	0.85 (3)
O1—C1—H1A	105 (3)	C11—C10—C3	121.0 (2)
O1—C1—H1B	111 (3)	C19—C10—C3	120.9 (2)
H1A—C1—H1B	117 (4)	O3—C11—C10	117.8 (2)
O1—C1—H1C	105 (4)	O3—C11—C12	120.4 (2)
H1A—C1—H1C	116 (5)	C10—C11—C12	121.7 (2)
H1B—C1—H1C	102 (4)	C13—C12—C11	120.2 (3)
O2—C2—N1	126.2 (2)	C13—C12—H12	120.3 (17)
O2—C2—O1	123.2 (2)	C11—C12—H12	119.5 (17)
N1—C2—O1	110.6 (2)	C12—C13—C14	121.4 (3)
N1—C3—C10	111.61 (19)	C12—C13—H13	120.3 (19)
N1—C3—C4	110.5 (2)	C14—C13—H13	118.4 (19)
C10—C3—C4	115.21 (19)	C13—C14—C15	121.9 (4)
N1—C3—H3	102.2 (14)	C13—C14—C19	118.6 (3)
C10—C3—H3	108.3 (14)	C15—C14—C19	119.5 (4)
C4—C3—H3	108.1 (14)	C16—C15—C14	121.1 (4)
C9—C4—C5	117.3 (3)	C16—C15—H15	123 (2)
C9—C4—C3	122.7 (2)	C14—C15—H15	116 (2)
C5—C4—C3	119.9 (2)	C15—C16—C17	120.3 (4)
C6—C5—C4	121.8 (3)	C15—C16—H16	122 (3)
C6—C5—H5	120.6 (19)	C17—C16—H16	118 (3)
C4—C5—H5	117.5 (19)	C18—C17—C16	121.3 (4)
C7—C6—C5	119.8 (3)	C18—C17—H17	111 (2)
C7—C6—H6	121 (2)	C16—C17—H17	128 (2)
C5—C6—H6	119 (2)	C17—C18—C19	120.4 (4)
C6—C7—C8	119.7 (3)	C17—C18—H18	121.0 (18)
C6—C7—H7	122 (2)	C19—C18—H18	118.6 (18)
C8—C7—H7	118 (2)	C18—C19—C14	117.4 (3)
C7—C8—C9	120.5 (3)	C18—C19—C10	122.7 (3)
C7—C8—H8	122.4 (19)	C14—C19—C10	119.9 (2)
C9—C8—H8	117.0 (19)	C2—N1—C3	123.6 (2)
C4—C9—C8	120.7 (3)	C2—N1—H1D	118.6 (19)
C4—C9—H9	118.1 (16)	C3—N1—H1D	117.0 (19)
C8—C9—H9	121.2 (16)	C2—O1—C1	116.6 (3)
C11—C10—C19	118.2 (2)	C11—O3—H3B	109.4 (19)
N1—C3—C4—C9	130.9 (2)	C12—C13—C14—C15	177.0 (3)
C10—C3—C4—C9	3.2 (3)	C12—C13—C14—C19	−1.9 (4)
N1—C3—C4—C5	−50.7 (3)	C13—C14—C15—C16	−178.2 (3)
C10—C3—C4—C5	−178.3 (2)	C19—C14—C15—C16	0.7 (5)
C9—C4—C5—C6	−0.7 (5)	C14—C15—C16—C17	0.0 (6)
C3—C4—C5—C6	−179.2 (3)	C15—C16—C17—C18	0.1 (7)
C4—C5—C6—C7	0.6 (6)	C16—C17—C18—C19	−0.7 (6)
C5—C6—C7—C8	−0.5 (6)	C17—C18—C19—C14	1.3 (4)
C6—C7—C8—C9	0.7 (6)	C17—C18—C19—C10	179.6 (3)
C5—C4—C9—C8	0.8 (4)	C13—C14—C19—C18	177.7 (3)
C3—C4—C9—C8	179.3 (2)	C15—C14—C19—C18	−1.3 (4)
C7—C8—C9—C4	−0.8 (5)	C13—C14—C19—C10	−0.7 (4)
N1—C3—C10—C11	−47.8 (3)	C15—C14—C19—C10	−179.6 (2)
C4—C3—C10—C11	79.3 (3)	C11—C10—C19—C18	−175.2 (2)
N1—C3—C10—C19	133.0 (2)	C3—C10—C19—C18	4.0 (4)
C4—C3—C10—C19	−99.9 (2)	C11—C10—C19—C14	3.0 (3)
C19—C10—C11—O3	176.0 (2)	C3—C10—C19—C14	−177.8 (2)
C3—C10—C11—O3	−3.2 (3)	O2—C2—N1—C3	−8.7 (4)
C19—C10—C11—C12	−3.0 (3)	O1—C2—N1—C3	172.6 (2)
C3—C10—C11—C12	177.8 (2)	C10—C3—N1—C2	−102.4 (3)
O3—C11—C12—C13	−178.5 (2)	C4—C3—N1—C2	128.0 (2)
C10—C11—C12—C13	0.5 (4)	O2—C2—O1—C1	4.8 (5)
C11—C12—C13—C14	2.0 (4)	N1—C2—O1—C1	−176.4 (4)