Crystal structure of phenyl N-(3,5-di­methyl­phenyl)carbamate

The asymmetric unit of the title carbamate, contains two independent mol­ecules (A and B) with similar conformations. In the crystal, they are arranged alternately, forming –A–B–A–B– chains linked by N—H...O(carbon­yl) hydrogen bonds, which extend along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.046
• wR factor = 0.143
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C27 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C25 Check
PLAT331_ALERT_2_C Small Average Phenyl   C-C Dist. C25    -C30           1.37 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C15 H15 N O2
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -4.504 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.028 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          3 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....         C7 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....         C8 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C22 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C23 Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          39 % Note

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

   4 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
   5 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Phenyl N-(3,5-dimethylphenyl)carbamate

Crystal data

C15H15NO2	Z = 4
Mr = 241.28	F(000) = 512
Triclinic, P1	Dx = 1.195 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4257 (4) Å	Cell parameters from 3376 reflections
b = 12.2054 (5) Å	θ = 1.7–25.0°
c = 13.2067 (6) Å	µ = 0.08 mm^−1
α = 62.979 (3)°	T = 293 K
β = 82.329 (3)°	Block, yellow
γ = 87.145 (3)°	0.20 × 0.18 × 0.17 mm
V = 1341.29 (10) Å^3

Data collection

Bruker SMART APEXII CCD diffractometer	4723 independent reflections
Radiation source: fine-focus sealed tube	3376 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.984, Tmax = 0.987	k = −14→14
31199 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.5754P] where P = (Fo^2 + 2Fc^2)/3
4723 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	1.58017 (15)	0.50462 (14)	0.15809 (14)	0.0562 (5)
O2	1.41427 (14)	0.39474 (15)	0.30750 (13)	0.0566 (6)
N1	1.64082 (17)	0.32555 (16)	0.29043 (15)	0.0457 (6)
C1	1.7338 (2)	0.1239 (2)	0.3932 (2)	0.0532 (8)
C2	1.7388 (3)	0.0131 (2)	0.4911 (3)	0.0626 (9)
C3	1.6482 (3)	−0.0046 (2)	0.5884 (2)	0.0642 (9)
O3	1.16793 (15)	0.29093 (14)	0.18417 (14)	0.0529 (6)
C4	1.5555 (3)	0.0854 (2)	0.5912 (2)	0.0590 (8)
O4	0.94345 (14)	0.36607 (14)	0.18663 (13)	0.0491 (5)
C5	1.5507 (2)	0.1955 (2)	0.4921 (2)	0.0503 (8)
C6	1.6388 (2)	0.21386 (19)	0.39347 (19)	0.0435 (7)
C7	1.8376 (4)	−0.0869 (3)	0.4895 (3)	0.0977 (13)
C8	1.4618 (4)	0.0653 (3)	0.6999 (2)	0.0914 (13)
C9	1.5337 (2)	0.40501 (19)	0.25803 (18)	0.0420 (7)
C10	1.4810 (2)	0.5974 (2)	0.10787 (19)	0.0505 (7)
C11	1.5007 (3)	0.7082 (2)	0.1060 (3)	0.0703 (10)
C12	1.4096 (4)	0.8039 (3)	0.0507 (3)	0.0948 (13)
C13	1.3023 (4)	0.7864 (3)	−0.0004 (3)	0.0933 (12)
C14	1.2842 (3)	0.6744 (3)	0.0022 (2)	0.0795 (12)
C15	1.3748 (2)	0.5789 (3)	0.0561 (2)	0.0595 (9)
N2	1.11656 (17)	0.40705 (15)	0.27069 (15)	0.0425 (6)
C16	1.1256 (2)	0.58070 (18)	0.30825 (17)	0.0422 (7)
C17	1.0624 (2)	0.66070 (19)	0.34863 (18)	0.0468 (7)
C18	0.9176 (2)	0.6468 (2)	0.38825 (19)	0.0505 (8)
C19	0.8359 (2)	0.5547 (2)	0.39031 (18)	0.0467 (7)
C20	0.9016 (2)	0.47436 (19)	0.35201 (17)	0.0418 (7)
C21	1.0452 (2)	0.48834 (17)	0.30963 (16)	0.0365 (6)
C22	1.1512 (3)	0.7594 (2)	0.3502 (3)	0.0725 (10)
C23	0.6792 (3)	0.5403 (3)	0.4352 (3)	0.0721 (10)
C24	1.0631 (2)	0.35729 (17)	0.21212 (17)	0.0382 (6)
C25	1.1406 (2)	0.24132 (19)	0.11142 (18)	0.0417 (7)
C26	1.1482 (3)	0.1170 (2)	0.1526 (2)	0.0724 (10)
C27	1.1370 (4)	0.0660 (3)	0.0796 (3)	0.0925 (13)
C28	1.1152 (3)	0.1379 (3)	−0.0306 (3)	0.0758 (12)
C29	1.1068 (3)	0.2615 (3)	−0.0702 (2)	0.0630 (9)
C30	1.1207 (2)	0.3150 (2)	0.0001 (2)	0.0522 (8)
H1	1.71910	0.34390	0.24420	0.0550*
H1A	1.79470	0.13780	0.32690	0.0640*
H3	1.64960	−0.07930	0.65390	0.0770*
H5	1.48810	0.25680	0.49240	0.0600*
H7A	1.89210	−0.05870	0.41510	0.1470*
H7B	1.78230	−0.15830	0.50600	0.1470*
H7C	1.90150	−0.10750	0.54620	0.1470*
H8A	1.40440	0.13660	0.68630	0.1370*
H8B	1.52060	0.05130	0.75850	0.1370*
H8C	1.40060	−0.00500	0.72410	0.1370*
H11	1.57400	0.71960	0.14110	0.0840*
H12	1.42170	0.88010	0.04850	0.1140*
H13	1.24120	0.85060	−0.03710	0.1120*
H14	1.21060	0.66280	−0.03260	0.0950*
H15	1.36370	0.50310	0.05710	0.0710*
H2	1.20280	0.38790	0.28630	0.0510*
H16	1.22240	0.58930	0.28020	0.0510*
H18	0.87400	0.70090	0.41420	0.0610*
H20	0.84890	0.41050	0.35480	0.0500*
H22A	1.24840	0.75510	0.31950	0.1090*
H22B	1.14850	0.74710	0.42760	0.1090*
H22C	1.11320	0.83870	0.30460	0.1090*
H23A	0.65130	0.60320	0.45820	0.1080*
H23B	0.66170	0.46090	0.49980	0.1080*
H23C	0.62440	0.54770	0.37610	0.1080*
H26	1.16080	0.06710	0.22880	0.0870*
H27	1.14440	−0.01860	0.10650	0.1110*
H28	1.10600	0.10280	−0.07880	0.0910*
H29	1.09160	0.31090	−0.14580	0.0760*
H30	1.11650	0.40000	−0.02780	0.0630*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0349 (8)	0.0558 (9)	0.0593 (10)	0.0080 (7)	−0.0001 (7)	−0.0123 (8)
O2	0.0302 (8)	0.0715 (11)	0.0554 (10)	0.0058 (7)	−0.0035 (7)	−0.0187 (8)
N1	0.0295 (8)	0.0500 (10)	0.0534 (11)	0.0029 (7)	−0.0028 (8)	−0.0207 (9)
C1	0.0442 (12)	0.0516 (13)	0.0670 (15)	0.0033 (10)	−0.0101 (11)	−0.0291 (12)
C2	0.0626 (15)	0.0462 (14)	0.0798 (19)	0.0059 (11)	−0.0270 (14)	−0.0250 (13)
C3	0.0729 (17)	0.0495 (14)	0.0649 (17)	−0.0067 (13)	−0.0275 (14)	−0.0155 (13)
O3	0.0406 (8)	0.0657 (10)	0.0743 (11)	0.0177 (7)	−0.0184 (7)	−0.0493 (9)
C4	0.0623 (15)	0.0627 (15)	0.0514 (14)	−0.0125 (12)	−0.0131 (12)	−0.0223 (12)
O4	0.0303 (7)	0.0692 (10)	0.0590 (10)	0.0036 (7)	−0.0066 (6)	−0.0388 (8)
C5	0.0461 (12)	0.0536 (13)	0.0551 (14)	−0.0013 (10)	−0.0083 (11)	−0.0272 (12)
C6	0.0359 (10)	0.0447 (12)	0.0534 (13)	−0.0014 (9)	−0.0127 (10)	−0.0231 (11)
C7	0.101 (2)	0.0603 (18)	0.126 (3)	0.0280 (17)	−0.033 (2)	−0.0349 (19)
C8	0.108 (3)	0.099 (2)	0.0551 (17)	−0.0149 (19)	−0.0002 (17)	−0.0254 (17)
C9	0.0308 (11)	0.0498 (12)	0.0473 (12)	0.0006 (9)	−0.0068 (9)	−0.0230 (11)
C10	0.0377 (11)	0.0548 (14)	0.0459 (13)	0.0068 (10)	0.0015 (10)	−0.0138 (11)
C11	0.0558 (15)	0.0610 (16)	0.087 (2)	0.0000 (12)	−0.0054 (14)	−0.0282 (15)
C12	0.084 (2)	0.0554 (18)	0.120 (3)	0.0092 (16)	0.006 (2)	−0.0237 (18)
C13	0.075 (2)	0.086 (2)	0.077 (2)	0.0306 (18)	−0.0041 (17)	−0.0048 (18)
C14	0.0532 (15)	0.123 (3)	0.0531 (16)	0.0237 (17)	−0.0125 (12)	−0.0324 (18)
C15	0.0443 (13)	0.0827 (18)	0.0530 (14)	0.0074 (12)	−0.0024 (11)	−0.0337 (13)
N2	0.0291 (8)	0.0530 (10)	0.0556 (11)	0.0062 (7)	−0.0086 (7)	−0.0332 (9)
C16	0.0387 (11)	0.0465 (12)	0.0404 (12)	−0.0029 (9)	−0.0024 (9)	−0.0192 (10)
C17	0.0582 (13)	0.0401 (11)	0.0411 (12)	−0.0021 (10)	−0.0078 (10)	−0.0169 (10)
C18	0.0579 (14)	0.0536 (13)	0.0463 (13)	0.0118 (11)	−0.0064 (11)	−0.0291 (11)
C19	0.0407 (11)	0.0610 (14)	0.0447 (12)	0.0064 (10)	−0.0052 (9)	−0.0299 (11)
C20	0.0358 (10)	0.0506 (12)	0.0431 (12)	−0.0009 (9)	−0.0025 (9)	−0.0252 (10)
C21	0.0345 (10)	0.0395 (10)	0.0353 (11)	0.0036 (8)	−0.0058 (8)	−0.0168 (9)
C22	0.090 (2)	0.0568 (15)	0.0774 (19)	−0.0152 (14)	−0.0020 (15)	−0.0368 (15)
C23	0.0452 (13)	0.105 (2)	0.085 (2)	0.0088 (13)	0.0023 (13)	−0.0629 (18)
C24	0.0307 (10)	0.0400 (11)	0.0419 (11)	0.0010 (8)	−0.0021 (8)	−0.0176 (9)
C25	0.0350 (10)	0.0473 (12)	0.0492 (13)	0.0049 (9)	−0.0086 (9)	−0.0269 (11)
C26	0.118 (2)	0.0460 (14)	0.0578 (16)	0.0122 (14)	−0.0381 (16)	−0.0215 (12)
C27	0.156 (3)	0.0517 (16)	0.090 (2)	0.0190 (18)	−0.057 (2)	−0.0402 (16)
C28	0.095 (2)	0.081 (2)	0.077 (2)	0.0157 (16)	−0.0331 (16)	−0.0534 (17)
C29	0.0631 (15)	0.0784 (18)	0.0446 (14)	0.0112 (13)	−0.0104 (11)	−0.0253 (13)
C30	0.0514 (13)	0.0453 (12)	0.0529 (14)	0.0058 (10)	−0.0045 (11)	−0.0172 (11)

Geometric parameters (Å, º)

O1—C9	1.361 (3)	C11—H11	0.9300
O1—C10	1.405 (3)	C12—H12	0.9300
O2—C9	1.205 (2)	C13—H13	0.9300
N1—C6	1.422 (3)	C14—H14	0.9300
N1—C9	1.336 (3)	C15—H15	0.9300
C1—C2	1.387 (4)	N2—H2	0.8600
C1—C6	1.383 (3)	C16—C21	1.381 (3)
N1—H1	0.8600	C16—C17	1.387 (3)
C2—C3	1.379 (4)	C17—C18	1.385 (3)
C2—C7	1.504 (5)	C17—C22	1.510 (4)
O3—C25	1.402 (3)	C18—C19	1.382 (3)
O3—C24	1.365 (3)	C19—C20	1.381 (3)
C3—C4	1.380 (4)	C19—C23	1.504 (4)
C4—C5	1.390 (3)	C20—C21	1.382 (3)
C4—C8	1.505 (4)	C25—C30	1.364 (3)
O4—C24	1.206 (2)	C25—C26	1.361 (4)
C5—C6	1.379 (3)	C26—C27	1.381 (5)
C10—C15	1.366 (3)	C27—C28	1.354 (5)
C10—C11	1.363 (4)	C28—C29	1.356 (5)
C11—C12	1.388 (5)	C29—C30	1.378 (4)
C12—C13	1.363 (5)	C16—H16	0.9300
C13—C14	1.370 (6)	C18—H18	0.9300
C14—C15	1.380 (4)	C20—H20	0.9300
C1—H1A	0.9300	C22—H22A	0.9600
N2—C24	1.335 (3)	C22—H22B	0.9600
N2—C21	1.416 (3)	C22—H22C	0.9600
C3—H3	0.9300	C23—H23A	0.9600
C5—H5	0.9300	C23—H23B	0.9600
C7—H7C	0.9600	C23—H23C	0.9600
C7—H7B	0.9600	C26—H26	0.9300
C7—H7A	0.9600	C27—H27	0.9300
C8—H8A	0.9600	C28—H28	0.9300
C8—H8C	0.9600	C29—H29	0.9300
C8—H8B	0.9600	C30—H30	0.9300
C9—O1—C10	117.78 (16)	C14—C15—H15	120.00
C6—N1—C9	126.72 (17)	C10—C15—H15	121.00
C2—C1—C6	120.4 (2)	C21—N2—H2	117.00
C6—N1—H1	117.00	C24—N2—H2	117.00
C9—N1—H1	117.00	C17—C16—C21	120.19 (18)
C3—C2—C7	120.9 (3)	C18—C17—C22	121.3 (2)
C1—C2—C3	118.6 (3)	C16—C17—C18	118.5 (2)
C1—C2—C7	120.5 (3)	C16—C17—C22	120.18 (19)
C2—C3—C4	121.8 (2)	C17—C18—C19	121.9 (2)
C24—O3—C25	118.46 (16)	C20—C19—C23	120.4 (2)
C3—C4—C5	118.9 (2)	C18—C19—C20	118.64 (19)
C3—C4—C8	120.6 (2)	C18—C19—C23	121.0 (2)
C5—C4—C8	120.4 (3)	C19—C20—C21	120.4 (2)
C4—C5—C6	120.0 (2)	C16—C21—C20	120.3 (2)
C1—C6—C5	120.2 (2)	N2—C21—C20	122.0 (2)
N1—C6—C5	122.4 (2)	N2—C21—C16	117.65 (17)
N1—C6—C1	117.29 (19)	O3—C24—O4	123.5 (2)
O1—C9—O2	123.5 (2)	O3—C24—N2	108.53 (17)
O1—C9—N1	109.16 (17)	O4—C24—N2	127.9 (2)
O2—C9—N1	127.3 (2)	O3—C25—C26	117.45 (19)
C11—C10—C15	121.6 (3)	C26—C25—C30	120.9 (2)
O1—C10—C11	117.6 (2)	O3—C25—C30	121.4 (2)
O1—C10—C15	120.6 (3)	C25—C26—C27	119.0 (2)
C10—C11—C12	118.9 (3)	C26—C27—C28	120.7 (4)
C11—C12—C13	120.2 (4)	C27—C28—C29	119.6 (3)
C12—C13—C14	120.2 (3)	C28—C29—C30	120.9 (3)
C13—C14—C15	120.2 (3)	C25—C30—C29	118.9 (3)
C10—C15—C14	119.0 (3)	C17—C16—H16	120.00
C6—C1—H1A	120.00	C21—C16—H16	120.00
C2—C1—H1A	120.00	C17—C18—H18	119.00
C21—N2—C24	126.38 (17)	C19—C18—H18	119.00
C2—C3—H3	119.00	C19—C20—H20	120.00
C4—C3—H3	119.00	C21—C20—H20	120.00
C6—C5—H5	120.00	C17—C22—H22A	109.00
C4—C5—H5	120.00	C17—C22—H22B	109.00
C2—C7—H7C	110.00	C17—C22—H22C	110.00
H7A—C7—H7B	109.00	H22A—C22—H22B	109.00
H7A—C7—H7C	109.00	H22A—C22—H22C	110.00
H7B—C7—H7C	109.00	H22B—C22—H22C	109.00
C2—C7—H7A	109.00	C19—C23—H23A	109.00
C2—C7—H7B	109.00	C19—C23—H23B	110.00
C4—C8—H8A	109.00	C19—C23—H23C	109.00
H8A—C8—H8B	110.00	H23A—C23—H23B	110.00
H8A—C8—H8C	109.00	H23A—C23—H23C	109.00
H8B—C8—H8C	109.00	H23B—C23—H23C	109.00
C4—C8—H8B	109.00	C25—C26—H26	121.00
C4—C8—H8C	109.00	C27—C26—H26	120.00
C10—C11—H11	121.00	C26—C27—H27	120.00
C12—C11—H11	121.00	C28—C27—H27	120.00
C11—C12—H12	120.00	C27—C28—H28	120.00
C13—C12—H12	120.00	C29—C28—H28	120.00
C14—C13—H13	120.00	C28—C29—H29	120.00
C12—C13—H13	120.00	C30—C29—H29	119.00
C13—C14—H14	120.00	C25—C30—H30	120.00
C15—C14—H14	120.00	C29—C30—H30	121.00
C10—O1—C9—N1	178.0 (2)	C10—C11—C12—C13	0.2 (5)
C9—O1—C10—C15	−72.6 (3)	C11—C12—C13—C14	−0.3 (5)
C9—O1—C10—C11	111.8 (3)	C12—C13—C14—C15	−0.3 (5)
C10—O1—C9—O2	−3.0 (3)	C13—C14—C15—C10	0.9 (4)
C6—N1—C9—O2	−3.2 (4)	C21—N2—C24—O4	−4.3 (4)
C9—N1—C6—C1	156.0 (2)	C24—N2—C21—C16	−144.0 (2)
C9—N1—C6—C5	−26.5 (4)	C24—N2—C21—C20	38.5 (3)
C6—N1—C9—O1	175.8 (2)	C21—N2—C24—O3	176.05 (18)
C6—C1—C2—C3	−0.6 (4)	C21—C16—C17—C18	−1.0 (3)
C6—C1—C2—C7	177.4 (3)	C21—C16—C17—C22	178.3 (2)
C2—C1—C6—N1	179.3 (2)	C17—C16—C21—N2	−178.04 (18)
C2—C1—C6—C5	1.7 (4)	C17—C16—C21—C20	−0.5 (3)
C7—C2—C3—C4	−179.2 (3)	C22—C17—C18—C19	−178.2 (2)
C1—C2—C3—C4	−1.2 (4)	C16—C17—C18—C19	1.1 (3)
C2—C3—C4—C8	−177.7 (3)	C17—C18—C19—C23	179.2 (2)
C25—O3—C24—O4	7.3 (3)	C17—C18—C19—C20	0.3 (3)
C2—C3—C4—C5	1.9 (4)	C18—C19—C20—C21	−1.8 (3)
C24—O3—C25—C26	−120.5 (2)	C23—C19—C20—C21	179.3 (2)
C25—O3—C24—N2	−173.11 (18)	C19—C20—C21—N2	179.34 (19)
C24—O3—C25—C30	65.6 (3)	C19—C20—C21—C16	1.9 (3)
C3—C4—C5—C6	−0.7 (4)	O3—C25—C26—C27	−173.2 (3)
C8—C4—C5—C6	178.9 (3)	C30—C25—C26—C27	0.7 (4)
C4—C5—C6—C1	−1.1 (3)	O3—C25—C30—C29	174.3 (2)
C4—C5—C6—N1	−178.5 (2)	C26—C25—C30—C29	0.7 (3)
C11—C10—C15—C14	−1.0 (4)	C25—C26—C27—C28	−1.6 (5)
O1—C10—C15—C14	−176.5 (2)	C26—C27—C28—C29	1.2 (5)
O1—C10—C11—C12	176.1 (3)	C27—C28—C29—C30	0.3 (4)
C15—C10—C11—C12	0.5 (4)	C28—C29—C30—C25	−1.2 (4)

Hydrogen-bond geometry (Å, º)

Cg2 and Cg3 are the centroids of rings C10–C15 and C16–C21, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4^i	0.86	2.14	2.957 (2)	159
N2—H2···O2	0.86	2.06	2.896 (2)	164
C16—H16···Cg2	0.93	2.93	3.659 (2)	136
C29—H29···Cg3^ii	0.93	2.59	3.508 (3)	173

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