Methyl­felbamate

The crystal structure of 2-meth­yl-2-phen­yl-1,3-propane­diol dicarbamate (methyl­felbamate), C₁₂H₁₆N₂O₄, contains two independent mol­ecules in the asymmetric unit. The hydrogen-bonding scheme is three-dimensional and involves inter­actions of the type N—H...O, C—H...O and N—H...(π-arene). Stereochemical and mol­ecular modelling investigations indicate that the mechanism for anti-epileptic action of the compound is probably different from those of other anticonvulsants.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.045
• wR factor = 0.111
• Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found





Alert level A
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5313

Author Response: ...'see _exptl_special_details'

PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6].....      55.00 Deg.

Author Response: ...'see _exptl_special_details'

PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      55.00 Deg.

Author Response: ...'see _exptl_special_details'

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.04 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C5A
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C1A
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C1A    -C6A           1.36 Ang.

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5313
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   9.3508
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.35
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O3A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C11A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C11B
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.12
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT420_ALERT_2_C D-H Without Acceptor       N2A    -   H103   ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N2B    -   H204   ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 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: Picker Operating Manual (Picker, 1967); cell refinement: Picker Operating Manual; data reduction: Picker Operating Manual; 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: SHELXL97.

2-Methyl-2-phenyl-1,3-propanediol dicarbamate

Crystal data

C12H16N2O4	Z = 4
Mr = 252.27	F(000) = 536
Triclinic, P1	Dx = 1.245 Mg m^−3
a = 9.984 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 12.040 (3) Å	Cell parameters from 16 reflections
c = 14.360 (4) Å	θ = 22–50°
α = 96.74 (2)°	µ = 0.79 mm^−1
β = 95.82 (2)°	T = 294 K
γ = 126.51 (3)°	Needle, colourless
V = 1345.8 (8) Å^3	0.5 × 0.2 × 0.2 mm

Data collection

Picker FACS-1 four-circle diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 55.0°, θmin = 3.2°
Ni-filtered radiation monochromator	h = 0→10
θ/2θ scans	k = −12→10
3626 measured reflections	l = −15→15
3385 independent reflections	3 standard reflections every 100 reflections
2591 reflections with I > 2σ(I)	intensity decay: 0.3%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0304P)^2 + 0.4196P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3385 reflections	Δρmax = 0.14 e Å^−3
362 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (5)

Special details

Experimental. There were no observable reflections above θ = 55°, only the background noise. High temperature factors for outer phenyl ring atoms are commented in the comment section. The data were collected on a crystal with dimensions 0.45 x 0.15 x. 10 mm mounted along its long axis.

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.

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

	x	y	z	Uiso*/Ueq
C1A	0.5149 (3)	0.9835 (3)	0.23702 (18)	0.0472 (7)
C2A	0.5844 (4)	0.9179 (4)	0.2572 (3)	0.0799 (10)
H2A	0.5585	0.8726	0.3082	0.132 (5)*
C3A	0.6925 (5)	0.9163 (5)	0.2044 (4)	0.1169 (16)
H3A	0.7368	0.8699	0.2204	0.132 (5)*
C4A	0.7329 (6)	0.9797 (6)	0.1319 (4)	0.1343 (19)
H4A	0.8045	0.9779	0.0962	0.132 (5)*
C5A	0.6684 (7)	1.0471 (7)	0.1106 (4)	0.168 (3)
H5A	0.6986	1.0946	0.0608	0.132 (5)*
C6A	0.5581 (5)	1.0471 (5)	0.1614 (3)	0.1156 (16)
H6A	0.5123	1.0918	0.1435	0.132 (5)*
C7A	0.3992 (3)	0.9867 (2)	0.29713 (16)	0.0416 (6)
C8A	0.2945 (3)	1.0244 (2)	0.24649 (16)	0.0447 (6)
H8A1	0.2296	1.0322	0.2891	0.067 (2)*
H8A2	0.3697	1.1150	0.2293	0.067 (2)*
C9A	0.5083 (3)	1.1022 (3)	0.38978 (19)	0.0585 (8)
H9A1	0.4351	1.0995	0.4305	0.067 (2)*
H9A2	0.5813	1.0858	0.4246	0.067 (2)*
C10A	0.1020 (3)	0.9488 (3)	0.10240 (17)	0.0417 (6)
C11A	0.7723 (3)	1.3340 (3)	0.41496 (18)	0.0504 (7)
C12A	0.2810 (3)	0.8479 (3)	0.32800 (19)	0.0519 (7)
H12A	0.2153	0.7712	0.2723	0.067 (2)*
H12B	0.2056	0.8523	0.3618	0.067 (2)*
H12C	0.3477	0.8325	0.3693	0.067 (2)*
O1A	0.1799 (2)	0.91556 (16)	0.16110 (11)	0.0468 (5)
O2A	0.1268 (2)	1.06209 (19)	0.11842 (12)	0.0592 (5)
O3A	0.6111 (2)	1.23877 (18)	0.36534 (14)	0.0727 (6)
O4A	0.8342 (2)	1.30945 (18)	0.47864 (13)	0.0594 (5)
N1A	−0.0057 (3)	0.8450 (3)	0.02634 (18)	0.0609 (7)
H101	−0.045 (3)	0.867 (3)	−0.017 (2)	0.056 (8)*
H102	−0.010 (3)	0.774 (3)	0.0180 (19)	0.055 (9)*
N2A	0.8478 (4)	1.4540 (3)	0.3871 (2)	0.0821 (10)
H103	0.793 (4)	1.465 (4)	0.339 (3)	0.098 (12)*
H104	0.946 (4)	1.526 (4)	0.419 (2)	0.085 (11)*
C1B	0.4971 (3)	0.4980 (3)	0.26383 (19)	0.0516 (7)
C2B	0.6577 (4)	0.6249 (3)	0.3006 (3)	0.0754 (10)
H2B	0.6752	0.6862	0.3548	0.132 (5)*
C3B	0.7931 (5)	0.6619 (5)	0.2576 (4)	0.1065 (15)
H3B	0.8996	0.7487	0.2829	0.132 (5)*
C4B	0.7742 (7)	0.5753 (7)	0.1803 (5)	0.1212 (18)
H4B	0.8665	0.6018	0.1526	0.132 (5)*
C5B	0.6180 (6)	0.4481 (5)	0.1431 (3)	0.1106 (14)
H5B	0.6038	0.3871	0.0899	0.132 (5)*
C6B	0.4797 (4)	0.4093 (4)	0.1842 (2)	0.0794 (10)
H6B	0.3738	0.3224	0.1579	0.132 (5)*
C7B	0.3437 (3)	0.4531 (2)	0.30873 (16)	0.0451 (6)
C8B	0.2885 (3)	0.3191 (3)	0.34336 (18)	0.0488 (7)
H8B1	0.2513	0.2438	0.2891	0.067 (2)*
H8B2	0.3837	0.3376	0.3871	0.067 (2)*
C9B	0.1962 (3)	0.4145 (3)	0.23310 (19)	0.0541 (7)
H9B1	0.1614	0.3358	0.1826	0.067 (2)*
H9B2	0.0994	0.3865	0.2617	0.067 (2)*
C10B	0.0965 (4)	0.1674 (3)	0.43385 (18)	0.0482 (7)
C11B	0.1554 (4)	0.5157 (3)	0.11300 (18)	0.0521 (7)
C12B	0.3844 (4)	0.5665 (3)	0.3921 (2)	0.0685 (9)
H12D	0.4732	0.5873	0.4417	0.067 (2)*
H12E	0.2841	0.5328	0.4171	0.067 (2)*
H12F	0.4217	0.6509	0.3700	0.067 (2)*
O1B	0.1502 (2)	0.27672 (18)	0.39171 (12)	0.0549 (5)
O2B	0.1623 (3)	0.1091 (2)	0.43483 (14)	0.0693 (6)
O3B	0.2520 (2)	0.53685 (17)	0.19402 (12)	0.0595 (5)
O4B	0.0244 (3)	0.4002 (2)	0.07246 (14)	0.0745 (7)
N1B	−0.0319 (4)	0.1358 (3)	0.4752 (2)	0.0659 (8)
H201	−0.071 (3)	0.179 (3)	0.4685 (19)	0.055 (9)*
H202	−0.085 (4)	0.063 (3)	0.501 (2)	0.076 (10)*
N2B	0.2187 (4)	0.6347 (3)	0.0825 (2)	0.0737 (9)
H203	0.163 (4)	0.632 (3)	0.033 (2)	0.069 (10)*
H204	0.314 (5)	0.710 (4)	0.115 (3)	0.115 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0373 (14)	0.0431 (14)	0.0555 (16)	0.0202 (12)	0.0084 (12)	0.0219 (12)
C2A	0.085 (2)	0.096 (2)	0.111 (3)	0.071 (2)	0.050 (2)	0.064 (2)
C3A	0.116 (3)	0.148 (4)	0.179 (4)	0.112 (3)	0.086 (3)	0.099 (4)
C4A	0.139 (4)	0.205 (5)	0.175 (5)	0.141 (4)	0.115 (4)	0.127 (4)
C5A	0.202 (5)	0.291 (7)	0.193 (5)	0.207 (6)	0.160 (5)	0.194 (6)
C6A	0.130 (3)	0.190 (4)	0.142 (4)	0.134 (4)	0.096 (3)	0.127 (4)
C7A	0.0403 (14)	0.0395 (14)	0.0419 (14)	0.0235 (12)	0.0018 (11)	0.0110 (11)
C8A	0.0453 (15)	0.0426 (14)	0.0395 (14)	0.0272 (12)	−0.0059 (12)	−0.0015 (11)
C9A	0.0574 (18)	0.0459 (16)	0.0524 (16)	0.0235 (14)	−0.0053 (13)	0.0126 (13)
C10A	0.0407 (15)	0.0419 (15)	0.0403 (14)	0.0247 (13)	0.0047 (12)	0.0094 (12)
C11A	0.0557 (17)	0.0408 (16)	0.0455 (15)	0.0278 (14)	−0.0027 (14)	0.0035 (13)
C12A	0.0482 (16)	0.0504 (16)	0.0527 (16)	0.0266 (14)	0.0116 (13)	0.0193 (13)
O1A	0.0493 (10)	0.0434 (9)	0.0432 (10)	0.0295 (9)	−0.0064 (8)	0.0031 (8)
O2A	0.0697 (13)	0.0538 (12)	0.0540 (11)	0.0433 (10)	−0.0124 (9)	−0.0004 (9)
O3A	0.0659 (13)	0.0413 (11)	0.0710 (13)	0.0182 (10)	−0.0279 (11)	0.0113 (9)
O4A	0.0513 (11)	0.0529 (11)	0.0636 (12)	0.0290 (10)	−0.0069 (9)	0.0146 (9)
N1A	0.0722 (18)	0.0456 (15)	0.0522 (15)	0.0357 (14)	−0.0170 (13)	−0.0007 (13)
N2A	0.075 (2)	0.0448 (16)	0.083 (2)	0.0188 (16)	−0.0245 (17)	0.0207 (14)
C1B	0.0521 (17)	0.0443 (15)	0.0549 (17)	0.0258 (14)	0.0089 (13)	0.0256 (13)
C2B	0.053 (2)	0.061 (2)	0.098 (2)	0.0271 (17)	0.0022 (18)	0.0321 (18)
C3B	0.051 (2)	0.096 (3)	0.170 (5)	0.037 (2)	0.021 (3)	0.074 (3)
C4B	0.097 (4)	0.136 (5)	0.183 (5)	0.079 (4)	0.085 (4)	0.112 (4)
C5B	0.123 (4)	0.116 (4)	0.117 (3)	0.075 (3)	0.074 (3)	0.053 (3)
C6B	0.080 (2)	0.071 (2)	0.077 (2)	0.0365 (19)	0.0397 (19)	0.0275 (19)
C7B	0.0551 (16)	0.0393 (14)	0.0370 (13)	0.0275 (13)	0.0023 (12)	0.0122 (11)
C8B	0.0574 (17)	0.0514 (16)	0.0479 (15)	0.0360 (14)	0.0168 (13)	0.0229 (12)
C9B	0.0591 (17)	0.0460 (15)	0.0537 (16)	0.0294 (14)	0.0062 (13)	0.0223 (13)
C10B	0.0615 (18)	0.0475 (15)	0.0471 (15)	0.0362 (14)	0.0209 (14)	0.0225 (12)
C11B	0.074 (2)	0.0514 (17)	0.0413 (15)	0.0448 (17)	0.0031 (14)	0.0105 (13)
C12B	0.096 (2)	0.0550 (18)	0.0526 (17)	0.0467 (18)	0.0082 (16)	0.0113 (14)
O1B	0.0694 (12)	0.0586 (11)	0.0623 (11)	0.0470 (10)	0.0303 (10)	0.0343 (9)
O2B	0.0938 (15)	0.0769 (14)	0.0891 (15)	0.0689 (13)	0.0539 (13)	0.0544 (12)
O3B	0.0688 (12)	0.0460 (10)	0.0514 (11)	0.0306 (10)	−0.0066 (9)	0.0171 (8)
O4B	0.0874 (16)	0.0480 (12)	0.0681 (13)	0.0377 (12)	−0.0227 (12)	0.0060 (10)
N1B	0.0785 (19)	0.0733 (19)	0.0854 (19)	0.0583 (17)	0.0451 (16)	0.0484 (16)
N2B	0.097 (2)	0.0552 (17)	0.0562 (17)	0.0436 (18)	−0.0120 (16)	0.0172 (14)

Geometric parameters (Å, º)

C1A—C6A	1.359 (4)	C1B—C2B	1.381 (4)
C1A—C2A	1.362 (4)	C1B—C6B	1.390 (4)
C1A—C7A	1.526 (4)	C1B—C7B	1.533 (4)
C2A—C3A	1.388 (5)	C2B—C3B	1.388 (5)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.317 (5)	C3B—C4B	1.343 (6)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.343 (6)	C4B—C5B	1.364 (6)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.381 (5)	C5B—C6B	1.391 (5)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.521 (3)	C7B—C9B	1.520 (3)
C7A—C12A	1.522 (3)	C7B—C12B	1.523 (4)
C7A—C9A	1.536 (3)	C7B—C8B	1.530 (3)
C8A—O1A	1.444 (3)	C8B—O1B	1.445 (3)
C8A—H8A1	0.9700	C8B—H8B1	0.9700
C8A—H8A2	0.9700	C8B—H8B2	0.9700
C9A—O3A	1.442 (3)	C9B—O3B	1.440 (3)
C9A—H9A1	0.9700	C9B—H9B1	0.9700
C9A—H9A2	0.9700	C9B—H9B2	0.9700
C10A—O2A	1.220 (3)	C10B—O2B	1.214 (3)
C10A—N1A	1.324 (3)	C10B—O1B	1.341 (3)
C10A—O1A	1.339 (3)	C10B—N1B	1.329 (4)
C11A—O4A	1.213 (3)	C11B—O4B	1.214 (3)
C11A—N2A	1.311 (3)	C11B—O3B	1.327 (3)
C11A—O3A	1.339 (3)	C11B—N2B	1.330 (4)
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
N1A—H101	0.86 (3)	N1B—H201	0.83 (3)
N1A—H102	0.82 (3)	N1B—H202	0.87 (3)
N2A—H103	0.90 (4)	N2B—H203	0.83 (3)
N2A—H104	0.86 (4)	N2B—H204	0.86 (4)
C6A—C1A—C2A	115.5 (3)	C2B—C1B—C6B	117.0 (3)
C6A—C1A—C7A	122.9 (3)	C2B—C1B—C7B	122.5 (3)
C2A—C1A—C7A	121.6 (2)	C6B—C1B—C7B	120.5 (2)
C1A—C2A—C3A	122.3 (3)	C1B—C2B—C3B	120.7 (4)
C1A—C2A—H2A	118.8	C1B—C2B—H2B	119.6
C3A—C2A—H2A	118.8	C3B—C2B—H2B	119.6
C4A—C3A—C2A	120.7 (4)	C4B—C3B—C2B	121.6 (4)
C4A—C3A—H3A	119.6	C4B—C3B—H3B	119.2
C2A—C3A—H3A	119.6	C2B—C3B—H3B	119.2
C3A—C4A—C5A	118.6 (4)	C5B—C4B—C3B	119.2 (4)
C3A—C4A—H4A	120.7	C5B—C4B—H4B	120.4
C5A—C4A—H4A	120.7	C3B—C4B—H4B	120.4
C4A—C5A—C6A	121.2 (4)	C4B—C5B—C6B	120.3 (4)
C4A—C5A—H5A	119.4	C4B—C5B—H5B	119.9
C6A—C5A—H5A	119.4	C6B—C5B—H5B	119.9
C1A—C6A—C5A	121.6 (3)	C1B—C6B—C5B	121.2 (3)
C1A—C6A—H6A	119.2	C1B—C6B—H6B	119.4
C5A—C6A—H6A	119.2	C5B—C6B—H6B	119.4
C8A—C7A—C12A	109.6 (2)	C9B—C7B—C12B	109.2 (2)
C8A—C7A—C1A	112.7 (2)	C9B—C7B—C1B	110.2 (2)
C12A—C7A—C1A	112.3 (2)	C12B—C7B—C1B	113.1 (2)
C8A—C7A—C9A	105.8 (2)	C9B—C7B—C8B	107.8 (2)
C12A—C7A—C9A	106.4 (2)	C12B—C7B—C8B	110.1 (2)
C1A—C7A—C9A	109.6 (2)	C1B—C7B—C8B	106.3 (2)
O1A—C8A—C7A	109.30 (18)	O1B—C8B—C7B	108.6 (2)
O1A—C8A—H8A1	109.8	O1B—C8B—H8B1	110.0
C7A—C8A—H8A1	109.8	C7B—C8B—H8B1	110.0
O1A—C8A—H8A2	109.8	O1B—C8B—H8B2	110.0
C7A—C8A—H8A2	109.8	C7B—C8B—H8B2	110.0
H8A1—C8A—H8A2	108.3	H8B1—C8B—H8B2	108.3
O3A—C9A—C7A	109.1 (2)	O3B—C9B—C7B	108.2 (2)
O3A—C9A—H9A1	109.9	O3B—C9B—H9B1	110.1
C7A—C9A—H9A1	109.9	C7B—C9B—H9B1	110.1
O3A—C9A—H9A2	109.9	O3B—C9B—H9B2	110.1
C7A—C9A—H9A2	109.9	C7B—C9B—H9B2	110.1
H9A1—C9A—H9A2	108.3	H9B1—C9B—H9B2	108.4
O2A—C10A—N1A	124.1 (2)	O2B—C10B—O1B	122.9 (2)
O2A—C10A—O1A	123.2 (2)	O2B—C10B—N1B	125.7 (2)
N1A—C10A—O1A	112.7 (2)	O1B—C10B—N1B	111.5 (2)
O4A—C11A—N2A	126.2 (3)	O4B—C11B—O3B	123.1 (2)
O4A—C11A—O3A	122.7 (2)	O4B—C11B—N2B	124.7 (3)
N2A—C11A—O3A	111.1 (3)	O3B—C11B—N2B	112.2 (3)
C7A—C12A—H12A	109.5	C7B—C12B—H12D	109.5
C7A—C12A—H12B	109.5	C7B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C7A—C12A—H12C	109.5	C7B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C10A—O1A—C8A	114.40 (18)	C10B—O1B—C8B	116.13 (19)
C11A—O3A—C9A	117.9 (2)	C11B—O3B—C9B	116.9 (2)
C10A—N1A—H101	115.2 (18)	C10B—N1B—H201	118.6 (19)
C10A—N1A—H102	118.5 (19)	C10B—N1B—H202	121 (2)
H101—N1A—H102	124 (3)	H201—N1B—H202	119 (3)
C11A—N2A—H103	121 (2)	C11B—N2B—H203	118 (2)
C11A—N2A—H104	119 (2)	C11B—N2B—H204	118 (3)
H103—N2A—H104	120 (3)	H203—N2B—H204	124 (3)
C6A—C1A—C2A—C3A	0.2 (6)	C6B—C1B—C2B—C3B	1.5 (4)
C7A—C1A—C2A—C3A	−178.8 (3)	C7B—C1B—C2B—C3B	−179.8 (3)
C1A—C2A—C3A—C4A	0.3 (7)	C1B—C2B—C3B—C4B	−1.3 (6)
C2A—C3A—C4A—C5A	0.6 (9)	C2B—C3B—C4B—C5B	0.2 (7)
C3A—C4A—C5A—C6A	−1.8 (10)	C3B—C4B—C5B—C6B	0.6 (7)
C2A—C1A—C6A—C5A	−1.4 (7)	C2B—C1B—C6B—C5B	−0.8 (5)
C7A—C1A—C6A—C5A	177.5 (4)	C7B—C1B—C6B—C5B	−179.5 (3)
C4A—C5A—C6A—C1A	2.4 (9)	C4B—C5B—C6B—C1B	−0.3 (6)
C6A—C1A—C7A—C8A	18.4 (4)	C2B—C1B—C7B—C9B	126.8 (3)
C2A—C1A—C7A—C8A	−162.7 (3)	C6B—C1B—C7B—C9B	−54.6 (3)
C6A—C1A—C7A—C12A	142.8 (3)	C2B—C1B—C7B—C12B	4.3 (3)
C2A—C1A—C7A—C12A	−38.4 (3)	C6B—C1B—C7B—C12B	−177.1 (3)
C6A—C1A—C7A—C9A	−99.1 (4)	C2B—C1B—C7B—C8B	−116.7 (3)
C2A—C1A—C7A—C9A	79.7 (3)	C6B—C1B—C7B—C8B	62.0 (3)
C12A—C7A—C8A—O1A	−62.1 (3)	C9B—C7B—C8B—O1B	−65.3 (3)
C1A—C7A—C8A—O1A	63.8 (3)	C12B—C7B—C8B—O1B	53.7 (3)
C9A—C7A—C8A—O1A	−176.43 (19)	C1B—C7B—C8B—O1B	176.57 (19)
C8A—C7A—C9A—O3A	−57.7 (3)	C12B—C7B—C9B—O3B	65.4 (3)
C12A—C7A—C9A—O3A	−174.2 (2)	C1B—C7B—C9B—O3B	−59.5 (3)
C1A—C7A—C9A—O3A	64.1 (3)	C8B—C7B—C9B—O3B	−175.1 (2)
O2A—C10A—O1A—C8A	1.0 (3)	O2B—C10B—O1B—C8B	2.4 (4)
N1A—C10A—O1A—C8A	−178.2 (2)	N1B—C10B—O1B—C8B	−179.3 (2)
C7A—C8A—O1A—C10A	−169.4 (2)	C7B—C8B—O1B—C10B	−174.4 (2)
O4A—C11A—O3A—C9A	0.3 (4)	O4B—C11B—O3B—C9B	0.7 (4)
N2A—C11A—O3A—C9A	−177.9 (3)	N2B—C11B—O3B—C9B	−179.4 (3)
C7A—C9A—O3A—C11A	−140.0 (2)	C7B—C9B—O3B—C11B	165.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H101···O2A^i	0.86 (3)	2.09 (3)	2.946 (3)	176 (3)
N1B—H201···O4A^ii	0.83 (3)	2.26 (3)	3.079 (3)	170 (3)
N1A—H102···O4B^iii	0.82 (3)	2.25 (3)	3.012 (4)	154 (3)
N1B—H202···O2B^iv	0.87 (3)	2.10 (3)	2.954 (3)	167 (3)
N2A—H104···O4A^v	0.86 (4)	2.09 (4)	2.936 (4)	169 (3)
N2B—H203···O4B^iii	0.83 (3)	2.10 (3)	2.914 (4)	166 (3)
C6B—H6B···O2A^vi	0.93	2.52	3.414 (4)	162
C8A—H8A1···O2B^vii	0.97	2.50	3.431 (3)	160
N2B—H204···Cg1	0.86 (4)	2.80 (4)	3.640 (4)	166 (4)
N2A—H103···Cg2^vii	0.90 (4)	2.72 (5)	3.619 (4)	169 (4)

Symmetry codes: (i) −x, −y+2, −z; (ii) x−1, y−1, z; (iii) −x, −y+1, −z; (iv) −x, −y, −z+1; (v) −x+2, −y+3, −z+1; (vi) x, y−1, z; (vii) x, y+1, z.