The title N-(pyridin-2-ylmethyl)benzamide derivative, crystallizes with two independent molecules (A and B) in the asymmetric unit, which differ essentially in the orientation of the pyridine ring with respect to the benzene ring, with the two rings being inclined to each other by 53.3 (2) and 72.9 (2)° in molecules A and B, respectively.
Supporting information
CCDC reference: 1954107
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.007 Å
- R factor = 0.053
- wR factor = 0.167
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level A
CHEM003_ALERT_1_A _chemical_formula_weight is missing
Chemical formula mass (Da).
The following tests will not be performed.
CHEMW_01,CHEMW_02,CHEMW_03,DENSD_01
PLAT043_ALERT_1_A Calculated and Reported Mol. Weight Differ by .. 348.34 Check
PLAT046_ALERT_1_A Reported Z, MW and D(calc) are Inconsistent .... 0.000 Check
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.78 Report
PLAT220_ALERT_2_C Non-Solvent Resd 2 C Ueq(max)/Ueq(min) Range 3.3 Ratio
PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C2A Check
PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C16B Check
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C11A Check
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C11B Check
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C14B Check
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00653 Ang.
PLAT352_ALERT_3_C Short N-H (X0.87,N1.01A) N1B - H1B . 0.75 Ang.
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C2A - C3A . 1.40 Ang.
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers .. 1 Check
Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 12 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 15 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info
3 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
11 ALERT level C = Check. Ensure it is not caused by an omission or oversight
5 ALERT level G = General information/check it is not something unexpected
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 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
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2013/1 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015) and PLATON (Spek, 2009).
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-
N-(pyridin-2-ylmethyl)\
benzamide
top
Crystal data top
C18H18F2N2O3 | Dx = 1.345 Mg m−3 |
Mr = 348.34 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 8521 reflections |
a = 13.4775 (12) Å | θ = 1.5–28.4° |
b = 28.026 (3) Å | µ = 0.11 mm−1 |
c = 9.1085 (9) Å | T = 293 K |
V = 3440.5 (6) Å3 | BLOCK, colourless |
Z = 8 | 0.30 × 0.25 × 0.20 mm |
F(000) = 1456 | |
Data collection top
Bruker SMART APEXII area-detector diffractometer | 5868 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.037 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 28.4°, θmin = 1.5° |
Tmin = 0.642, Tmax = 0.785 | h = −16→17 |
33263 measured reflections | k = −37→37 |
8521 independent reflections | l = −10→12 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: mixed |
wR(F2) = 0.167 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0901P)2 + 0.6343P] where P = (Fo2 + 2Fc2)/3 |
8521 reflections | (Δ/σ)max < 0.001 |
459 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C3A | 0.6926 (5) | 0.85621 (17) | 0.0399 (6) | 0.0849 (15) | |
H3A | 0.760513 | 0.868025 | 0.052106 | 0.102* | |
C3B | 0.8930 (3) | 0.64609 (14) | 0.4443 (5) | 0.0594 (10) | |
H3B | 0.824697 | 0.634683 | 0.432638 | 0.071* | |
C1B | 0.9416 (4) | 0.63426 (16) | 0.5869 (5) | 0.0770 (14) | |
H1B1 | 0.988434 | 0.657112 | 0.626991 | 0.092* | |
H1B2 | 0.902904 | 0.617075 | 0.659464 | 0.092* | |
C1A | 0.6470 (6) | 0.8684 (2) | −0.0992 (6) | 0.0997 (19) | |
H1A1 | 0.686226 | 0.886135 | −0.169794 | 0.120* | |
H1A2 | 0.600245 | 0.845892 | −0.141389 | 0.120* | |
C2A | 0.6200 (6) | 0.8918 (2) | 0.0358 (7) | 0.111 (2) | |
H2A1 | 0.641359 | 0.924536 | 0.049262 | 0.134* | |
H2A2 | 0.555580 | 0.884387 | 0.077600 | 0.134* | |
C2B | 0.9698 (4) | 0.60887 (18) | 0.4527 (6) | 0.0821 (14) | |
H2B1 | 0.948720 | 0.575924 | 0.442855 | 0.098* | |
H2B2 | 1.034168 | 0.615922 | 0.410413 | 0.098* | |
C4B | 0.9158 (3) | 0.69265 (12) | 0.3746 (4) | 0.0533 (9) | |
H4B1 | 0.871794 | 0.717173 | 0.412054 | 0.064* | |
H4B2 | 0.983671 | 0.701907 | 0.395770 | 0.064* | |
C4A | 0.6728 (4) | 0.80972 (14) | 0.1111 (4) | 0.0599 (10) | |
H4A1 | 0.605344 | 0.799607 | 0.090866 | 0.072* | |
H4A2 | 0.717818 | 0.785685 | 0.073220 | 0.072* | |
C5A | 0.6758 (3) | 0.77698 (11) | 0.3535 (4) | 0.0421 (7) | |
C5B | 0.9153 (3) | 0.72633 (11) | 0.1320 (4) | 0.0418 (7) | |
C10A | 0.6486 (3) | 0.73121 (12) | 0.3097 (4) | 0.0423 (7) | |
H10A | 0.636984 | 0.725073 | 0.210853 | 0.051* | |
C10B | 0.9444 (3) | 0.77079 (12) | 0.1793 (4) | 0.0425 (7) | |
H10B | 0.956199 | 0.775829 | 0.278668 | 0.051* | |
C9A | 0.6385 (2) | 0.69462 (11) | 0.4113 (3) | 0.0398 (7) | |
C9B | 0.9564 (2) | 0.80857 (11) | 0.0804 (3) | 0.0393 (7) | |
C8B | 0.9374 (3) | 0.80117 (12) | −0.0676 (4) | 0.0443 (7) | |
H8B | 0.944975 | 0.825994 | −0.134414 | 0.053* | |
C8A | 0.6566 (3) | 0.70345 (12) | 0.5597 (4) | 0.0450 (8) | |
H8A | 0.649867 | 0.679050 | 0.628203 | 0.054* | |
C7A | 0.6847 (3) | 0.74862 (12) | 0.6046 (4) | 0.0467 (8) | |
H7A | 0.696901 | 0.754677 | 0.703354 | 0.056* | |
C7B | 0.9069 (3) | 0.75644 (12) | −0.1152 (4) | 0.0471 (8) | |
H7B | 0.894040 | 0.751332 | −0.214280 | 0.057* | |
C6A | 0.6947 (3) | 0.78472 (11) | 0.5024 (4) | 0.0428 (7) | |
C6B | 0.8957 (3) | 0.71980 (11) | −0.0171 (4) | 0.0441 (8) | |
C11B | 0.7764 (3) | 0.65960 (13) | −0.0361 (4) | 0.0556 (9) | |
H11B | 0.770549 | 0.653960 | 0.069771 | 0.067* | |
C11A | 0.8125 (3) | 0.84507 (12) | 0.5158 (4) | 0.0523 (9) | |
H11A | 0.820805 | 0.846015 | 0.408994 | 0.063* | |
C12A | 0.6111 (3) | 0.64577 (11) | 0.3570 (3) | 0.0399 (7) | |
C12B | 0.9851 (3) | 0.85610 (11) | 0.1403 (3) | 0.0394 (7) | |
C13B | 1.0486 (3) | 0.93630 (12) | 0.0893 (4) | 0.0527 (9) | |
H13A | 1.112422 | 0.944908 | 0.047812 | 0.063* | |
H13B | 1.053716 | 0.938497 | 0.195349 | 0.063* | |
C13A | 0.5474 (3) | 0.56661 (11) | 0.4218 (4) | 0.0504 (9) | |
H13C | 0.558990 | 0.560555 | 0.318366 | 0.060* | |
H13D | 0.477237 | 0.561821 | 0.440582 | 0.060* | |
C14A | 0.6056 (3) | 0.53127 (11) | 0.5106 (4) | 0.0468 (8) | |
C14B | 0.9714 (3) | 0.97029 (12) | 0.0361 (5) | 0.0574 (10) | |
C15A | 0.6971 (3) | 0.54131 (14) | 0.5656 (5) | 0.0604 (10) | |
H15A | 0.726593 | 0.570913 | 0.550449 | 0.072* | |
C15B | 0.8969 (5) | 0.9869 (2) | 0.1237 (8) | 0.0966 (18) | |
H15B | 0.893675 | 0.977774 | 0.221716 | 0.116* | |
C16A | 0.7455 (4) | 0.50557 (19) | 0.6458 (7) | 0.0808 (14) | |
H16A | 0.808325 | 0.511136 | 0.684333 | 0.097* | |
C16B | 0.8265 (6) | 1.0173 (3) | 0.0664 (11) | 0.128 (3) | |
H16B | 0.774980 | 1.029011 | 0.124056 | 0.154* | |
C17A | 0.7010 (5) | 0.46329 (18) | 0.6668 (7) | 0.0911 (17) | |
H17A | 0.732284 | 0.439371 | 0.720385 | 0.109* | |
C17B | 0.8351 (6) | 1.0297 (2) | −0.0794 (11) | 0.122 (3) | |
H17B | 0.787592 | 1.048970 | −0.124001 | 0.146* | |
C18A | 0.6109 (5) | 0.45618 (16) | 0.6094 (7) | 0.0910 (17) | |
H18A | 0.580764 | 0.426749 | 0.624739 | 0.109* | |
C18B | 0.9148 (6) | 1.0132 (2) | −0.1574 (7) | 0.108 (2) | |
H18B | 0.922244 | 1.023375 | −0.253996 | 0.130* | |
N1A | 0.5726 (3) | 0.61610 (10) | 0.4539 (3) | 0.0465 (7) | |
N1B | 1.0244 (3) | 0.88763 (10) | 0.0482 (4) | 0.0473 (7) | |
N2B | 0.9813 (4) | 0.98388 (15) | −0.1035 (4) | 0.0834 (13) | |
N2A | 0.5614 (3) | 0.48899 (12) | 0.5308 (5) | 0.0714 (10) | |
O1B | 0.9022 (2) | 0.68714 (8) | 0.2187 (3) | 0.0538 (6) | |
O1A | 0.6868 (2) | 0.81526 (8) | 0.2653 (3) | 0.0573 (7) | |
O2A | 0.7199 (2) | 0.83023 (8) | 0.5524 (3) | 0.0547 (7) | |
O2B | 0.8688 (2) | 0.67504 (9) | −0.0719 (3) | 0.0547 (7) | |
O3A | 0.6272 (2) | 0.63485 (8) | 0.2278 (3) | 0.0527 (6) | |
O3B | 0.9710 (2) | 0.86563 (9) | 0.2718 (3) | 0.0555 (7) | |
F2B | 0.7076 (2) | 0.69107 (10) | −0.0828 (3) | 0.0810 (8) | |
F1A | 0.8220 (3) | 0.88794 (10) | 0.5731 (5) | 0.1111 (12) | |
F2A | 0.8810 (2) | 0.81731 (11) | 0.5780 (4) | 0.0885 (9) | |
F1B | 0.7623 (3) | 0.61959 (10) | −0.1115 (4) | 0.0974 (10) | |
H1A | 0.552 (3) | 0.6261 (14) | 0.535 (5) | 0.053 (11)* | |
H1B | 1.040 (3) | 0.8804 (13) | −0.028 (4) | 0.039 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C3A | 0.108 (4) | 0.075 (3) | 0.072 (3) | 0.002 (3) | −0.004 (3) | 0.018 (2) |
C3B | 0.059 (2) | 0.059 (2) | 0.060 (2) | −0.0020 (18) | 0.0005 (19) | 0.0089 (18) |
C1B | 0.107 (4) | 0.073 (3) | 0.051 (3) | −0.007 (2) | −0.003 (2) | 0.016 (2) |
C1A | 0.146 (6) | 0.095 (4) | 0.059 (3) | 0.009 (4) | −0.003 (3) | 0.021 (3) |
C2A | 0.140 (6) | 0.097 (4) | 0.097 (5) | 0.029 (4) | 0.011 (4) | 0.001 (3) |
C2B | 0.088 (4) | 0.071 (3) | 0.087 (4) | 0.017 (2) | 0.003 (3) | 0.019 (3) |
C4B | 0.064 (2) | 0.0516 (18) | 0.044 (2) | −0.0016 (17) | −0.0037 (17) | 0.0031 (16) |
C4A | 0.074 (3) | 0.058 (2) | 0.047 (2) | −0.0015 (19) | −0.0061 (19) | 0.0088 (17) |
C5A | 0.0406 (19) | 0.0444 (16) | 0.0414 (18) | 0.0031 (13) | 0.0003 (14) | 0.0035 (13) |
C5B | 0.0406 (18) | 0.0454 (15) | 0.0395 (18) | 0.0010 (13) | 0.0013 (13) | 0.0041 (13) |
C10A | 0.0437 (19) | 0.0486 (16) | 0.0346 (17) | 0.0018 (14) | −0.0049 (13) | 0.0002 (13) |
C10B | 0.045 (2) | 0.0489 (16) | 0.0334 (17) | 0.0004 (14) | −0.0027 (13) | 0.0028 (13) |
C9A | 0.0374 (17) | 0.0476 (15) | 0.0344 (16) | 0.0033 (13) | −0.0024 (13) | −0.0009 (13) |
C9B | 0.0331 (16) | 0.0482 (16) | 0.0365 (17) | 0.0019 (12) | 0.0008 (12) | 0.0013 (13) |
C8B | 0.0449 (18) | 0.0546 (17) | 0.0334 (17) | −0.0044 (14) | −0.0005 (13) | 0.0037 (14) |
C8A | 0.0497 (19) | 0.0513 (17) | 0.0341 (18) | −0.0008 (14) | 0.0002 (14) | 0.0031 (14) |
C7A | 0.049 (2) | 0.0578 (19) | 0.0330 (17) | −0.0058 (16) | −0.0019 (14) | −0.0040 (15) |
C7B | 0.047 (2) | 0.0619 (19) | 0.0323 (17) | −0.0067 (16) | −0.0003 (14) | −0.0025 (15) |
C6A | 0.0392 (19) | 0.0469 (16) | 0.0425 (19) | −0.0003 (13) | 0.0027 (14) | −0.0071 (14) |
C6B | 0.0366 (18) | 0.0520 (17) | 0.0437 (19) | −0.0042 (14) | 0.0038 (14) | −0.0079 (14) |
C11B | 0.062 (3) | 0.060 (2) | 0.045 (2) | −0.0165 (18) | −0.0007 (17) | 0.0005 (17) |
C11A | 0.052 (2) | 0.0510 (18) | 0.054 (2) | −0.0069 (16) | 0.0001 (17) | 0.0023 (16) |
C12A | 0.0417 (18) | 0.0445 (15) | 0.0337 (16) | 0.0048 (13) | −0.0034 (13) | 0.0018 (13) |
C12B | 0.0420 (18) | 0.0430 (15) | 0.0330 (16) | 0.0010 (13) | −0.0020 (13) | 0.0020 (13) |
C13B | 0.068 (3) | 0.0457 (17) | 0.044 (2) | −0.0066 (16) | −0.0037 (18) | 0.0005 (15) |
C13A | 0.062 (2) | 0.0428 (16) | 0.047 (2) | −0.0025 (15) | −0.0055 (17) | −0.0020 (14) |
C14A | 0.056 (2) | 0.0431 (16) | 0.0416 (19) | 0.0038 (15) | 0.0052 (15) | −0.0040 (14) |
C14B | 0.071 (3) | 0.0446 (17) | 0.057 (2) | −0.0013 (17) | 0.001 (2) | −0.0065 (16) |
C15A | 0.052 (2) | 0.065 (2) | 0.065 (3) | 0.0005 (18) | −0.0015 (19) | 0.0017 (19) |
C15B | 0.097 (4) | 0.093 (3) | 0.100 (4) | 0.018 (3) | 0.032 (4) | 0.019 (3) |
C16A | 0.060 (3) | 0.092 (3) | 0.090 (4) | 0.016 (2) | −0.011 (3) | 0.004 (3) |
C16B | 0.105 (5) | 0.116 (5) | 0.163 (8) | 0.044 (4) | 0.028 (5) | 0.004 (5) |
C17A | 0.116 (5) | 0.067 (3) | 0.091 (4) | 0.027 (3) | −0.020 (3) | 0.013 (3) |
C17B | 0.129 (6) | 0.094 (4) | 0.142 (7) | 0.048 (4) | −0.048 (5) | −0.014 (4) |
C18A | 0.121 (5) | 0.053 (2) | 0.099 (4) | −0.005 (3) | −0.022 (4) | 0.018 (2) |
C18B | 0.153 (7) | 0.098 (4) | 0.073 (4) | 0.053 (4) | −0.029 (4) | −0.003 (3) |
N1A | 0.0626 (19) | 0.0413 (13) | 0.0355 (16) | −0.0002 (13) | 0.0056 (13) | −0.0034 (12) |
N1B | 0.063 (2) | 0.0443 (14) | 0.0343 (16) | 0.0007 (13) | 0.0049 (14) | 0.0010 (13) |
N2B | 0.115 (4) | 0.083 (2) | 0.052 (2) | 0.035 (2) | −0.007 (2) | 0.002 (2) |
N2A | 0.086 (3) | 0.0524 (17) | 0.076 (3) | −0.0080 (17) | −0.015 (2) | 0.0087 (17) |
O1B | 0.0715 (19) | 0.0454 (12) | 0.0445 (14) | −0.0040 (12) | −0.0072 (12) | 0.0056 (10) |
O1A | 0.075 (2) | 0.0483 (13) | 0.0487 (15) | −0.0047 (12) | −0.0070 (13) | 0.0062 (11) |
O2A | 0.0512 (16) | 0.0537 (13) | 0.0593 (16) | −0.0064 (11) | 0.0102 (12) | −0.0142 (12) |
O2B | 0.0600 (17) | 0.0553 (13) | 0.0488 (15) | −0.0113 (11) | 0.0107 (12) | −0.0133 (11) |
O3A | 0.0662 (17) | 0.0570 (13) | 0.0349 (13) | −0.0037 (12) | 0.0031 (11) | −0.0057 (10) |
O3B | 0.0734 (19) | 0.0597 (14) | 0.0336 (13) | −0.0128 (13) | 0.0001 (12) | −0.0025 (11) |
F2B | 0.0607 (16) | 0.0891 (17) | 0.093 (2) | −0.0114 (13) | −0.0134 (14) | 0.0211 (15) |
F1A | 0.095 (2) | 0.0660 (15) | 0.172 (4) | −0.0286 (15) | 0.019 (2) | −0.0379 (19) |
F2A | 0.0591 (16) | 0.1027 (19) | 0.104 (2) | −0.0103 (14) | −0.0187 (15) | 0.0355 (17) |
F1B | 0.110 (2) | 0.0744 (16) | 0.108 (2) | −0.0407 (16) | 0.0166 (19) | −0.0294 (16) |
Geometric parameters (Å, º) top
C3A—C2A | 1.397 (9) | C7B—H7B | 0.9300 |
C3A—C1A | 1.449 (8) | C6A—O2A | 1.396 (4) |
C3A—C4A | 1.479 (6) | C6B—O2B | 1.398 (4) |
C3A—H3A | 0.9800 | C11B—F1B | 1.329 (4) |
C3B—C2B | 1.471 (6) | C11B—F2B | 1.348 (5) |
C3B—C4B | 1.484 (5) | C11B—O2B | 1.359 (5) |
C3B—C1B | 1.492 (6) | C11B—H11B | 0.9800 |
C3B—H3B | 0.9800 | C11A—F1A | 1.316 (4) |
C1B—C2B | 1.465 (7) | C11A—F2A | 1.334 (5) |
C1B—H1B1 | 0.9700 | C11A—O2A | 1.357 (5) |
C1B—H1B2 | 0.9700 | C11A—H11A | 0.9800 |
C1A—C2A | 1.441 (8) | C12A—O3A | 1.235 (4) |
C1A—H1A1 | 0.9700 | C12A—N1A | 1.319 (4) |
C1A—H1A2 | 0.9700 | C12B—O3B | 1.242 (4) |
C2A—H2A1 | 0.9700 | C12B—N1B | 1.328 (4) |
C2A—H2A2 | 0.9700 | C13B—N1B | 1.452 (4) |
C2B—H2B1 | 0.9700 | C13B—C14B | 1.492 (6) |
C2B—H2B2 | 0.9700 | C13B—H13A | 0.9700 |
C4B—O1B | 1.440 (4) | C13B—H13B | 0.9700 |
C4B—H4B1 | 0.9700 | C13A—N1A | 1.458 (4) |
C4B—H4B2 | 0.9700 | C13A—C14A | 1.500 (5) |
C4A—O1A | 1.426 (5) | C13A—H13C | 0.9700 |
C4A—H4A1 | 0.9700 | C13A—H13D | 0.9700 |
C4A—H4A2 | 0.9700 | C14A—N2A | 1.339 (5) |
C5A—O1A | 1.349 (4) | C14A—C15A | 1.361 (6) |
C5A—C10A | 1.392 (5) | C14B—N2B | 1.333 (6) |
C5A—C6A | 1.397 (5) | C14B—C15B | 1.365 (7) |
C5B—O1B | 1.365 (4) | C15A—C16A | 1.400 (6) |
C5B—C10B | 1.375 (5) | C15A—H15A | 0.9300 |
C5B—C6B | 1.395 (5) | C15B—C16B | 1.378 (10) |
C10A—C9A | 1.388 (5) | C15B—H15B | 0.9300 |
C10A—H10A | 0.9300 | C16A—C17A | 1.342 (8) |
C10B—C9B | 1.399 (4) | C16A—H16A | 0.9300 |
C10B—H10B | 0.9300 | C16B—C17B | 1.378 (11) |
C9A—C8A | 1.396 (5) | C16B—H16B | 0.9300 |
C9A—C12A | 1.501 (4) | C17A—C18A | 1.337 (9) |
C9B—C8B | 1.388 (5) | C17A—H17A | 0.9300 |
C9B—C12B | 1.490 (4) | C17B—C18B | 1.369 (11) |
C8B—C7B | 1.389 (5) | C17B—H17B | 0.9300 |
C8B—H8B | 0.9300 | C18A—N2A | 1.343 (6) |
C8A—C7A | 1.383 (5) | C18A—H18A | 0.9300 |
C8A—H8A | 0.9300 | C18B—N2B | 1.312 (7) |
C7A—C6A | 1.381 (5) | C18B—H18B | 0.9300 |
C7A—H7A | 0.9300 | N1A—H1A | 0.83 (4) |
C7B—C6B | 1.370 (5) | N1B—H1B | 0.75 (4) |
| | | |
C2A—C3A—C1A | 60.8 (4) | C7A—C6A—O2A | 118.2 (3) |
C2A—C3A—C4A | 120.9 (6) | C7A—C6A—C5A | 121.5 (3) |
C1A—C3A—C4A | 120.9 (5) | O2A—C6A—C5A | 120.2 (3) |
C2A—C3A—H3A | 114.6 | C7B—C6B—C5B | 121.1 (3) |
C1A—C3A—H3A | 114.6 | C7B—C6B—O2B | 117.9 (3) |
C4A—C3A—H3A | 114.6 | C5B—C6B—O2B | 121.0 (3) |
C2B—C3B—C4B | 120.0 (4) | F1B—C11B—F2B | 106.9 (3) |
C2B—C3B—C1B | 59.2 (3) | F1B—C11B—O2B | 106.0 (3) |
C4B—C3B—C1B | 118.5 (4) | F2B—C11B—O2B | 110.3 (3) |
C2B—C3B—H3B | 115.8 | F1B—C11B—H11B | 111.2 |
C4B—C3B—H3B | 115.8 | F2B—C11B—H11B | 111.2 |
C1B—C3B—H3B | 115.8 | O2B—C11B—H11B | 111.2 |
C2B—C1B—C3B | 59.7 (3) | F1A—C11A—F2A | 107.2 (4) |
C2B—C1B—H1B1 | 117.8 | F1A—C11A—O2A | 105.8 (3) |
C3B—C1B—H1B1 | 117.8 | F2A—C11A—O2A | 110.7 (3) |
C2B—C1B—H1B2 | 117.8 | F1A—C11A—H11A | 111.0 |
C3B—C1B—H1B2 | 117.8 | F2A—C11A—H11A | 111.0 |
H1B1—C1B—H1B2 | 114.9 | O2A—C11A—H11A | 111.0 |
C2A—C1A—C3A | 57.8 (4) | O3A—C12A—N1A | 123.4 (3) |
C2A—C1A—H1A1 | 118.0 | O3A—C12A—C9A | 119.8 (3) |
C3A—C1A—H1A1 | 118.0 | N1A—C12A—C9A | 116.8 (3) |
C2A—C1A—H1A2 | 118.0 | O3B—C12B—N1B | 121.8 (3) |
C3A—C1A—H1A2 | 118.0 | O3B—C12B—C9B | 120.3 (3) |
H1A1—C1A—H1A2 | 115.2 | N1B—C12B—C9B | 117.8 (3) |
C3A—C2A—C1A | 61.3 (4) | N1B—C13B—C14B | 111.1 (3) |
C3A—C2A—H2A1 | 117.6 | N1B—C13B—H13A | 109.4 |
C1A—C2A—H2A1 | 117.6 | C14B—C13B—H13A | 109.4 |
C3A—C2A—H2A2 | 117.6 | N1B—C13B—H13B | 109.4 |
C1A—C2A—H2A2 | 117.6 | C14B—C13B—H13B | 109.4 |
H2A1—C2A—H2A2 | 114.7 | H13A—C13B—H13B | 108.0 |
C1B—C2B—C3B | 61.1 (3) | N1A—C13A—C14A | 113.4 (3) |
C1B—C2B—H2B1 | 117.7 | N1A—C13A—H13C | 108.9 |
C3B—C2B—H2B1 | 117.7 | C14A—C13A—H13C | 108.9 |
C1B—C2B—H2B2 | 117.7 | N1A—C13A—H13D | 108.9 |
C3B—C2B—H2B2 | 117.7 | C14A—C13A—H13D | 108.9 |
H2B1—C2B—H2B2 | 114.8 | H13C—C13A—H13D | 107.7 |
O1B—C4B—C3B | 107.5 (3) | N2A—C14A—C15A | 122.4 (4) |
O1B—C4B—H4B1 | 110.2 | N2A—C14A—C13A | 115.2 (4) |
C3B—C4B—H4B1 | 110.2 | C15A—C14A—C13A | 122.4 (3) |
O1B—C4B—H4B2 | 110.2 | N2B—C14B—C15B | 122.2 (5) |
C3B—C4B—H4B2 | 110.2 | N2B—C14B—C13B | 115.0 (4) |
H4B1—C4B—H4B2 | 108.5 | C15B—C14B—C13B | 122.8 (4) |
O1A—C4A—C3A | 108.2 (4) | C14A—C15A—C16A | 117.8 (4) |
O1A—C4A—H4A1 | 110.1 | C14A—C15A—H15A | 121.1 |
C3A—C4A—H4A1 | 110.1 | C16A—C15A—H15A | 121.1 |
O1A—C4A—H4A2 | 110.1 | C14B—C15B—C16B | 119.8 (6) |
C3A—C4A—H4A2 | 110.1 | C14B—C15B—H15B | 120.1 |
H4A1—C4A—H4A2 | 108.4 | C16B—C15B—H15B | 120.1 |
O1A—C5A—C10A | 126.2 (3) | C17A—C16A—C15A | 119.9 (5) |
O1A—C5A—C6A | 115.8 (3) | C17A—C16A—H16A | 120.1 |
C10A—C5A—C6A | 118.0 (3) | C15A—C16A—H16A | 120.1 |
O1B—C5B—C10B | 125.8 (3) | C17B—C16B—C15B | 117.6 (7) |
O1B—C5B—C6B | 115.7 (3) | C17B—C16B—H16B | 121.2 |
C10B—C5B—C6B | 118.5 (3) | C15B—C16B—H16B | 121.2 |
C9A—C10A—C5A | 121.0 (3) | C18A—C17A—C16A | 118.8 (5) |
C9A—C10A—H10A | 119.5 | C18A—C17A—H17A | 120.6 |
C5A—C10A—H10A | 119.5 | C16A—C17A—H17A | 120.6 |
C5B—C10B—C9B | 121.1 (3) | C18B—C17B—C16B | 118.7 (6) |
C5B—C10B—H10B | 119.4 | C18B—C17B—H17B | 120.6 |
C9B—C10B—H10B | 119.4 | C16B—C17B—H17B | 120.6 |
C10A—C9A—C8A | 119.8 (3) | C17A—C18A—N2A | 123.9 (5) |
C10A—C9A—C12A | 118.6 (3) | C17A—C18A—H18A | 118.0 |
C8A—C9A—C12A | 121.6 (3) | N2A—C18A—H18A | 118.0 |
C8B—C9B—C10B | 119.4 (3) | N2B—C18B—C17B | 123.6 (6) |
C8B—C9B—C12B | 122.5 (3) | N2B—C18B—H18B | 118.2 |
C10B—C9B—C12B | 118.1 (3) | C17B—C18B—H18B | 118.2 |
C9B—C8B—C7B | 119.5 (3) | C12A—N1A—C13A | 123.9 (3) |
C9B—C8B—H8B | 120.2 | C12A—N1A—H1A | 121 (3) |
C7B—C8B—H8B | 120.2 | C13A—N1A—H1A | 115 (3) |
C7A—C8A—C9A | 119.8 (3) | C12B—N1B—C13B | 123.5 (3) |
C7A—C8A—H8A | 120.1 | C12B—N1B—H1B | 121 (3) |
C9A—C8A—H8A | 120.1 | C13B—N1B—H1B | 115 (3) |
C6A—C7A—C8A | 119.9 (3) | C18B—N2B—C14B | 117.9 (5) |
C6A—C7A—H7A | 120.1 | C14A—N2A—C18A | 117.2 (4) |
C8A—C7A—H7A | 120.1 | C5B—O1B—C4B | 117.9 (3) |
C6B—C7B—C8B | 120.4 (3) | C5A—O1A—C4A | 119.1 (3) |
C6B—C7B—H7B | 119.8 | C11A—O2A—C6A | 115.0 (3) |
C8B—C7B—H7B | 119.8 | C11B—O2B—C6B | 116.0 (3) |
| | | |
C4B—C3B—C1B—C2B | −109.8 (5) | C10B—C9B—C12B—N1B | 160.6 (3) |
C4A—C3A—C1A—C2A | 110.6 (7) | N1A—C13A—C14A—N2A | 154.4 (4) |
C4A—C3A—C2A—C1A | −110.6 (7) | N1A—C13A—C14A—C15A | −26.1 (5) |
C4B—C3B—C2B—C1B | 107.3 (5) | N1B—C13B—C14B—N2B | −82.7 (4) |
C2B—C3B—C4B—O1B | 84.0 (5) | N1B—C13B—C14B—C15B | 98.2 (5) |
C1B—C3B—C4B—O1B | 153.0 (4) | N2A—C14A—C15A—C16A | 0.1 (6) |
C2A—C3A—C4A—O1A | −81.6 (7) | C13A—C14A—C15A—C16A | −179.4 (4) |
C1A—C3A—C4A—O1A | −153.9 (5) | N2B—C14B—C15B—C16B | 2.7 (10) |
O1A—C5A—C10A—C9A | −179.3 (3) | C13B—C14B—C15B—C16B | −178.3 (6) |
C6A—C5A—C10A—C9A | 1.3 (5) | C14A—C15A—C16A—C17A | −0.5 (8) |
O1B—C5B—C10B—C9B | 179.4 (3) | C14B—C15B—C16B—C17B | −0.1 (12) |
C6B—C5B—C10B—C9B | −1.4 (5) | C15A—C16A—C17A—C18A | 0.4 (9) |
C5A—C10A—C9A—C8A | −0.6 (5) | C15B—C16B—C17B—C18B | −3.0 (13) |
C5A—C10A—C9A—C12A | −178.7 (3) | C16A—C17A—C18A—N2A | 0.1 (10) |
C5B—C10B—C9B—C8B | 0.9 (5) | C16B—C17B—C18B—N2B | 3.9 (12) |
C5B—C10B—C9B—C12B | 178.2 (3) | O3A—C12A—N1A—C13A | 2.1 (6) |
C10B—C9B—C8B—C7B | −0.1 (5) | C9A—C12A—N1A—C13A | −176.3 (3) |
C12B—C9B—C8B—C7B | −177.3 (3) | C14A—C13A—N1A—C12A | 117.2 (4) |
C10A—C9A—C8A—C7A | −0.1 (5) | O3B—C12B—N1B—C13B | −3.8 (6) |
C12A—C9A—C8A—C7A | 177.9 (3) | C9B—C12B—N1B—C13B | 175.2 (3) |
C9A—C8A—C7A—C6A | 0.0 (5) | C14B—C13B—N1B—C12B | −101.4 (4) |
C9B—C8B—C7B—C6B | 0.0 (5) | C17B—C18B—N2B—C14B | −1.5 (11) |
C8A—C7A—C6A—O2A | 177.8 (3) | C15B—C14B—N2B—C18B | −1.9 (8) |
C8A—C7A—C6A—C5A | 0.8 (5) | C13B—C14B—N2B—C18B | 179.0 (5) |
O1A—C5A—C6A—C7A | 179.1 (3) | C15A—C14A—N2A—C18A | 0.3 (7) |
C10A—C5A—C6A—C7A | −1.5 (5) | C13A—C14A—N2A—C18A | 179.8 (5) |
O1A—C5A—C6A—O2A | 2.1 (5) | C17A—C18A—N2A—C14A | −0.4 (9) |
C10A—C5A—C6A—O2A | −178.4 (3) | C10B—C5B—O1B—C4B | 2.7 (5) |
C8B—C7B—C6B—C5B | −0.5 (5) | C6B—C5B—O1B—C4B | −176.5 (3) |
C8B—C7B—C6B—O2B | −177.4 (3) | C3B—C4B—O1B—C5B | 177.4 (3) |
O1B—C5B—C6B—C7B | −179.5 (3) | C10A—C5A—O1A—C4A | −2.0 (6) |
C10B—C5B—C6B—C7B | 1.2 (5) | C6A—C5A—O1A—C4A | 177.5 (3) |
O1B—C5B—C6B—O2B | −2.7 (5) | C3A—C4A—O1A—C5A | −178.0 (4) |
C10B—C5B—C6B—O2B | 178.1 (3) | F1A—C11A—O2A—C6A | −179.5 (3) |
C10A—C9A—C12A—O3A | 21.9 (5) | F2A—C11A—O2A—C6A | −63.7 (4) |
C8A—C9A—C12A—O3A | −156.1 (3) | C7A—C6A—O2A—C11A | 110.5 (4) |
C10A—C9A—C12A—N1A | −159.6 (3) | C5A—C6A—O2A—C11A | −72.5 (4) |
C8A—C9A—C12A—N1A | 22.4 (5) | F1B—C11B—O2B—C6B | 173.3 (3) |
C8B—C9B—C12B—O3B | 156.8 (3) | F2B—C11B—O2B—C6B | 58.0 (4) |
C10B—C9B—C12B—O3B | −20.3 (5) | C7B—C6B—O2B—C11B | −111.5 (4) |
C8B—C9B—C12B—N1B | −22.2 (5) | C5B—C6B—O2B—C11B | 71.5 (4) |
Hydrogen-bond geometry (Å, º) topCg2, Cg3 and Cg6 are the centroids of the
N2A/C14A–C18A, C5A–C10A and
C5B–C10B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11A—H11A···O3B | 0.98 | 2.44 | 3.136 (5) | 128 |
C11B—H11B···O3A | 0.98 | 2.47 | 3.210 (5) | 132 |
C4B—H4B1···Cg3 | 0.97 | 2.87 | 3.689 (4) | 143 |
C4A—H4A2···Cg6 | 0.97 | 2.90 | 3.717 (5) | 143 |
N1A—H1A···O3Bi | 0.84 (4) | 2.08 (4) | 2.895 (4) | 163 (4) |
N1B—H1B···O3Aii | 0.75 (4) | 2.21 (4) | 2.939 (4) | 164 (4) |
C13A—H13C···N2Biii | 0.97 | 2.55 | 3.347 (5) | 140 |
C13A—H13D···F1Ai | 0.97 | 2.52 | 3.294 (6) | 136 |
C13B—H13B···Cg2iv | 0.97 | 2.73 | 3.748 (4) | 137 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x+1/2, −y+3/2, −z; (iii) x−1/2, −y+3/2, −z; (iv) x+1/2, −y+3/2, −z+1. |